diff --git a/.dprint.json b/.dprint.json
index 082eb30058..ea99f2aeda 100644
--- a/.dprint.json
+++ b/.dprint.json
@@ -68,8 +68,8 @@
     "third_party"
   ],
   "plugins": [
-    "https://plugins.dprint.dev/typescript-0.93.0.wasm",
-    "https://plugins.dprint.dev/json-0.19.3.wasm",
+    "https://plugins.dprint.dev/typescript-0.93.1.wasm",
+    "https://plugins.dprint.dev/json-0.19.4.wasm",
     "https://plugins.dprint.dev/markdown-0.17.8.wasm",
     "https://plugins.dprint.dev/toml-0.6.3.wasm",
     "https://plugins.dprint.dev/exec-0.5.0.json@8d9972eee71fa1590e04873540421f3eda7674d0f1aae3d7c788615e7b7413d0",
diff --git a/.github/workflows/cargo_publish.yml b/.github/workflows/cargo_publish.yml
index f77286c7d4..f285b78919 100644
--- a/.github/workflows/cargo_publish.yml
+++ b/.github/workflows/cargo_publish.yml
@@ -2,6 +2,11 @@ name: cargo_publish
 
 on: workflow_dispatch
 
+# Ensures only one publish is running at a time
+concurrency:
+  group: ${{ github.workflow }}
+  cancel-in-progress: true
+
 jobs:
   build:
     name: cargo publish
@@ -28,7 +33,7 @@ jobs:
       - uses: dsherret/rust-toolchain-file@v1
 
       - name: Install deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
 
diff --git a/.github/workflows/ci.generate.ts b/.github/workflows/ci.generate.ts
index c03f10bc92..49d11107d5 100755
--- a/.github/workflows/ci.generate.ts
+++ b/.github/workflows/ci.generate.ts
@@ -5,10 +5,10 @@ import { stringify } from "jsr:@std/yaml@^0.221/stringify";
 // Bump this number when you want to purge the cache.
 // Note: the tools/release/01_bump_crate_versions.ts script will update this version
 // automatically via regex, so ensure that this line maintains this format.
-const cacheVersion = 18;
+const cacheVersion = 23;
 
-const ubuntuX86Runner = "ubuntu-22.04";
-const ubuntuX86XlRunner = "ubuntu-22.04-xl";
+const ubuntuX86Runner = "ubuntu-24.04";
+const ubuntuX86XlRunner = "ubuntu-24.04-xl";
 const ubuntuARMRunner = "ubicloud-standard-16-arm";
 const windowsX86Runner = "windows-2022";
 const windowsX86XlRunner = "windows-2022-xl";
@@ -59,7 +59,7 @@ const prCacheKeyPrefix =
   `${cacheVersion}-cargo-target-\${{ matrix.os }}-\${{ matrix.arch }}-\${{ matrix.profile }}-\${{ matrix.job }}-`;
 
 // Note that you may need to add more version to the `apt-get remove` line below if you change this
-const llvmVersion = 18;
+const llvmVersion = 19;
 const installPkgsCommand =
   `sudo apt-get install --no-install-recommends clang-${llvmVersion} lld-${llvmVersion} clang-tools-${llvmVersion} clang-format-${llvmVersion} clang-tidy-${llvmVersion}`;
 const sysRootStep = {
@@ -71,7 +71,7 @@ export DEBIAN_FRONTEND=noninteractive
 sudo apt-get -qq remove --purge -y man-db  > /dev/null 2> /dev/null
 # Remove older clang before we install
 sudo apt-get -qq remove \
-  'clang-12*' 'clang-13*' 'clang-14*' 'clang-15*' 'clang-16*' 'llvm-12*' 'llvm-13*' 'llvm-14*' 'llvm-15*' 'llvm-16*' 'lld-12*' 'lld-13*' 'lld-14*' 'lld-15*' 'lld-16*' > /dev/null 2> /dev/null
+  'clang-12*' 'clang-13*' 'clang-14*' 'clang-15*' 'clang-16*' 'clang-17*' 'clang-18*' 'llvm-12*' 'llvm-13*' 'llvm-14*' 'llvm-15*' 'llvm-16*' 'lld-12*' 'lld-13*' 'lld-14*' 'lld-15*' 'lld-16*' 'lld-17*' 'lld-18*' > /dev/null 2> /dev/null
 
 # Install clang-XXX, lld-XXX, and debootstrap.
 echo "deb http://apt.llvm.org/jammy/ llvm-toolchain-jammy-${llvmVersion} main" |
@@ -86,7 +86,7 @@ ${installPkgsCommand} || echo 'Failed. Trying again.' && sudo apt-get clean && s
 (yes '' | sudo update-alternatives --force --all) > /dev/null 2> /dev/null || true
 
 echo "Decompressing sysroot..."
-wget -q https://github.com/denoland/deno_sysroot_build/releases/download/sysroot-20240528/sysroot-\`uname -m\`.tar.xz -O /tmp/sysroot.tar.xz
+wget -q https://github.com/denoland/deno_sysroot_build/releases/download/sysroot-20241030/sysroot-\`uname -m\`.tar.xz -O /tmp/sysroot.tar.xz
 cd /
 xzcat /tmp/sysroot.tar.xz | sudo tar -x
 sudo mount --rbind /dev /sysroot/dev
@@ -193,7 +193,7 @@ const installNodeStep = {
 };
 const installDenoStep = {
   name: "Install Deno",
-  uses: "denoland/setup-deno@v1",
+  uses: "denoland/setup-deno@v2",
   with: { "deno-version": "v1.x" },
 };
 
@@ -751,11 +751,11 @@ const ci = {
           ].join("\n"),
           run: [
             "cd target/release",
-            "shasum -a 256 deno > deno-${{ matrix.arch }}-unknown-linux-gnu.sha256sum",
             "zip -r deno-${{ matrix.arch }}-unknown-linux-gnu.zip deno",
+            "shasum -a 256 deno-${{ matrix.arch }}-unknown-linux-gnu.zip > deno-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum",
             "strip denort",
-            "shasum -a 256 denort > denort-${{ matrix.arch }}-unknown-linux-gnu.sha256sum",
             "zip -r denort-${{ matrix.arch }}-unknown-linux-gnu.zip denort",
+            "shasum -a 256 denort-${{ matrix.arch }}-unknown-linux-gnu.zip > denort-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum",
             "./deno types > lib.deno.d.ts",
           ].join("\n"),
         },
@@ -779,11 +779,11 @@ const ci = {
             "--p12-file=<(echo $APPLE_CODESIGN_KEY | base64 -d) " +
             "--entitlements-xml-file=cli/entitlements.plist",
             "cd target/release",
-            "shasum -a 256 deno > deno-${{ matrix.arch }}-apple-darwin.sha256sum",
             "zip -r deno-${{ matrix.arch }}-apple-darwin.zip deno",
+            "shasum -a 256 deno-${{ matrix.arch }}-apple-darwin.zip > deno-${{ matrix.arch }}-apple-darwin.zip.sha256sum",
             "strip denort",
-            "shasum -a 256 denort > denort-${{ matrix.arch }}-apple-darwin.sha256sum",
             "zip -r denort-${{ matrix.arch }}-apple-darwin.zip denort",
+            "shasum -a 256 denort-${{ matrix.arch }}-apple-darwin.zip > denort-${{ matrix.arch }}-apple-darwin.zip.sha256sum",
           ]
             .join("\n"),
         },
@@ -797,10 +797,10 @@ const ci = {
           ].join("\n"),
           shell: "pwsh",
           run: [
-            "Get-FileHash target/release/deno.exe -Algorithm SHA256 | Format-List > target/release/deno-${{ matrix.arch }}-pc-windows-msvc.sha256sum",
             "Compress-Archive -CompressionLevel Optimal -Force -Path target/release/deno.exe -DestinationPath target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip",
-            "Get-FileHash target/release/denort.exe -Algorithm SHA256 | Format-List > target/release/denort-${{ matrix.arch }}-pc-windows-msvc.sha256sum",
+            "Get-FileHash target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum",
             "Compress-Archive -CompressionLevel Optimal -Force -Path target/release/denort.exe -DestinationPath target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip",
+            "Get-FileHash target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum",
           ].join("\n"),
         },
         {
@@ -1045,25 +1045,25 @@ const ci = {
           with: {
             files: [
               "target/release/deno-x86_64-pc-windows-msvc.zip",
-              "target/release/deno-x86_64-pc-windows-msvc.sha256sum",
+              "target/release/deno-x86_64-pc-windows-msvc.zip.sha256sum",
               "target/release/denort-x86_64-pc-windows-msvc.zip",
-              "target/release/denort-x86_64-pc-windows-msvc.sha256sum",
+              "target/release/denort-x86_64-pc-windows-msvc.zip.sha256sum",
               "target/release/deno-x86_64-unknown-linux-gnu.zip",
-              "target/release/deno-x86_64-unknown-linux-gnu.sha256sum",
+              "target/release/deno-x86_64-unknown-linux-gnu.zip.sha256sum",
               "target/release/denort-x86_64-unknown-linux-gnu.zip",
-              "target/release/denort-x86_64-unknown-linux-gnu.sha256sum",
+              "target/release/denort-x86_64-unknown-linux-gnu.zip.sha256sum",
               "target/release/deno-x86_64-apple-darwin.zip",
-              "target/release/deno-x86_64-apple-darwin.sha256sum",
+              "target/release/deno-x86_64-apple-darwin.zip.sha256sum",
               "target/release/denort-x86_64-apple-darwin.zip",
-              "target/release/denort-x86_64-apple-darwin.sha256sum",
+              "target/release/denort-x86_64-apple-darwin.zip.sha256sum",
               "target/release/deno-aarch64-unknown-linux-gnu.zip",
-              "target/release/deno-aarch64-unknown-linux-gnu.sha256sum",
+              "target/release/deno-aarch64-unknown-linux-gnu.zip.sha256sum",
               "target/release/denort-aarch64-unknown-linux-gnu.zip",
-              "target/release/denort-aarch64-unknown-linux-gnu.sha256sum",
+              "target/release/denort-aarch64-unknown-linux-gnu.zip.sha256sum",
               "target/release/deno-aarch64-apple-darwin.zip",
-              "target/release/deno-aarch64-apple-darwin.sha256sum",
+              "target/release/deno-aarch64-apple-darwin.zip.sha256sum",
               "target/release/denort-aarch64-apple-darwin.zip",
-              "target/release/denort-aarch64-apple-darwin.sha256sum",
+              "target/release/denort-aarch64-apple-darwin.zip.sha256sum",
               "target/release/deno_src.tar.gz",
               "target/release/lib.deno.d.ts",
             ].join("\n"),
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 701d67f93c..a9c06de17a 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -62,7 +62,7 @@ jobs:
             profile: debug
           - os: macos
             arch: x86_64
-            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-22.04'' || ''macos-13'' }}'
+            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-24.04'' || ''macos-13'' }}'
             job: test
             profile: release
             skip: '${{ !contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'') }}'
@@ -73,7 +73,7 @@ jobs:
             profile: debug
           - os: macos
             arch: aarch64
-            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-22.04'' || ''macos-14'' }}'
+            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-24.04'' || ''macos-14'' }}'
             job: test
             profile: release
             skip: '${{ !contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'') }}'
@@ -84,33 +84,33 @@ jobs:
             profile: debug
           - os: windows
             arch: x86_64
-            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-22.04'' || github.repository == ''denoland/deno'' && ''windows-2022-xl'' || ''windows-2022'' }}'
+            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'')) && ''ubuntu-24.04'' || github.repository == ''denoland/deno'' && ''windows-2022-xl'' || ''windows-2022'' }}'
             job: test
             profile: release
             skip: '${{ !contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'') }}'
           - os: linux
             arch: x86_64
-            runner: '${{ github.repository == ''denoland/deno'' && ''ubuntu-22.04-xl'' || ''ubuntu-22.04'' }}'
+            runner: '${{ github.repository == ''denoland/deno'' && ''ubuntu-24.04-xl'' || ''ubuntu-24.04'' }}'
             job: test
             profile: release
             use_sysroot: true
             wpt: '${{ !startsWith(github.ref, ''refs/tags/'') }}'
           - os: linux
             arch: x86_64
-            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'' && !contains(github.event.pull_request.labels.*.name, ''ci-bench''))) && ''ubuntu-22.04'' || github.repository == ''denoland/deno'' && ''ubuntu-22.04-xl'' || ''ubuntu-22.04'' }}'
+            runner: '${{ (!contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'' && !contains(github.event.pull_request.labels.*.name, ''ci-bench''))) && ''ubuntu-24.04'' || github.repository == ''denoland/deno'' && ''ubuntu-24.04-xl'' || ''ubuntu-24.04'' }}'
             job: bench
             profile: release
             use_sysroot: true
             skip: '${{ !contains(github.event.pull_request.labels.*.name, ''ci-full'') && (github.event_name == ''pull_request'' && !contains(github.event.pull_request.labels.*.name, ''ci-bench'')) }}'
           - os: linux
             arch: x86_64
-            runner: ubuntu-22.04
+            runner: ubuntu-24.04
             job: test
             profile: debug
             use_sysroot: true
           - os: linux
             arch: x86_64
-            runner: ubuntu-22.04
+            runner: ubuntu-24.04
             job: lint
             profile: debug
           - os: linux
@@ -178,7 +178,7 @@ jobs:
         if: '!(matrix.skip)'
       - if: '!(matrix.skip) && (matrix.job == ''lint'' || matrix.job == ''test'' || matrix.job == ''bench'')'
         name: Install Deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
       - name: Install Python
@@ -252,22 +252,22 @@ jobs:
           # to complete.
           sudo apt-get -qq remove --purge -y man-db  > /dev/null 2> /dev/null
           # Remove older clang before we install
-          sudo apt-get -qq remove   'clang-12*' 'clang-13*' 'clang-14*' 'clang-15*' 'clang-16*' 'llvm-12*' 'llvm-13*' 'llvm-14*' 'llvm-15*' 'llvm-16*' 'lld-12*' 'lld-13*' 'lld-14*' 'lld-15*' 'lld-16*' > /dev/null 2> /dev/null
+          sudo apt-get -qq remove   'clang-12*' 'clang-13*' 'clang-14*' 'clang-15*' 'clang-16*' 'clang-17*' 'clang-18*' 'llvm-12*' 'llvm-13*' 'llvm-14*' 'llvm-15*' 'llvm-16*' 'lld-12*' 'lld-13*' 'lld-14*' 'lld-15*' 'lld-16*' 'lld-17*' 'lld-18*' > /dev/null 2> /dev/null
 
           # Install clang-XXX, lld-XXX, and debootstrap.
-          echo "deb http://apt.llvm.org/jammy/ llvm-toolchain-jammy-18 main" |
-            sudo dd of=/etc/apt/sources.list.d/llvm-toolchain-jammy-18.list
+          echo "deb http://apt.llvm.org/jammy/ llvm-toolchain-jammy-19 main" |
+            sudo dd of=/etc/apt/sources.list.d/llvm-toolchain-jammy-19.list
           curl https://apt.llvm.org/llvm-snapshot.gpg.key |
             gpg --dearmor                                 |
           sudo dd of=/etc/apt/trusted.gpg.d/llvm-snapshot.gpg
           sudo apt-get update
           # this was unreliable sometimes, so try again if it fails
-          sudo apt-get install --no-install-recommends clang-18 lld-18 clang-tools-18 clang-format-18 clang-tidy-18 || echo 'Failed. Trying again.' && sudo apt-get clean && sudo apt-get update && sudo apt-get install --no-install-recommends clang-18 lld-18 clang-tools-18 clang-format-18 clang-tidy-18
+          sudo apt-get install --no-install-recommends clang-19 lld-19 clang-tools-19 clang-format-19 clang-tidy-19 || echo 'Failed. Trying again.' && sudo apt-get clean && sudo apt-get update && sudo apt-get install --no-install-recommends clang-19 lld-19 clang-tools-19 clang-format-19 clang-tidy-19
           # Fix alternatives
           (yes '' | sudo update-alternatives --force --all) > /dev/null 2> /dev/null || true
 
           echo "Decompressing sysroot..."
-          wget -q https://github.com/denoland/deno_sysroot_build/releases/download/sysroot-20240528/sysroot-`uname -m`.tar.xz -O /tmp/sysroot.tar.xz
+          wget -q https://github.com/denoland/deno_sysroot_build/releases/download/sysroot-20241030/sysroot-`uname -m`.tar.xz -O /tmp/sysroot.tar.xz
           cd /
           xzcat /tmp/sysroot.tar.xz | sudo tar -x
           sudo mount --rbind /dev /sysroot/dev
@@ -299,8 +299,8 @@ jobs:
           CARGO_PROFILE_RELEASE_LTO=false
           RUSTFLAGS<<__1
             -C linker-plugin-lto=true
-            -C linker=clang-18
-            -C link-arg=-fuse-ld=lld-18
+            -C linker=clang-19
+            -C link-arg=-fuse-ld=lld-19
             -C link-arg=-ldl
             -C link-arg=-Wl,--allow-shlib-undefined
             -C link-arg=-Wl,--thinlto-cache-dir=$(pwd)/target/release/lto-cache
@@ -310,8 +310,8 @@ jobs:
           __1
           RUSTDOCFLAGS<<__1
             -C linker-plugin-lto=true
-            -C linker=clang-18
-            -C link-arg=-fuse-ld=lld-18
+            -C linker=clang-19
+            -C link-arg=-fuse-ld=lld-19
             -C link-arg=-ldl
             -C link-arg=-Wl,--allow-shlib-undefined
             -C link-arg=-Wl,--thinlto-cache-dir=$(pwd)/target/release/lto-cache
@@ -319,7 +319,7 @@ jobs:
             --cfg tokio_unstable
             $RUSTFLAGS
           __1
-          CC=/usr/bin/clang-18
+          CC=/usr/bin/clang-19
           CFLAGS=-flto=thin $CFLAGS
           " > $GITHUB_ENV
       - name: Remove macOS cURL --ipv4 flag
@@ -361,8 +361,8 @@ jobs:
           path: |-
             ~/.cargo/registry/index
             ~/.cargo/registry/cache
-          key: '18-cargo-home-${{ matrix.os }}-${{ matrix.arch }}-${{ hashFiles(''Cargo.lock'') }}'
-          restore-keys: '18-cargo-home-${{ matrix.os }}-${{ matrix.arch }}'
+          key: '23-cargo-home-${{ matrix.os }}-${{ matrix.arch }}-${{ hashFiles(''Cargo.lock'') }}'
+          restore-keys: '23-cargo-home-${{ matrix.os }}-${{ matrix.arch }}'
         if: '!(matrix.skip)'
       - name: Restore cache build output (PR)
         uses: actions/cache/restore@v4
@@ -375,7 +375,7 @@ jobs:
             !./target/*/*.zip
             !./target/*/*.tar.gz
           key: never_saved
-          restore-keys: '18-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-'
+          restore-keys: '23-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-'
       - name: Apply and update mtime cache
         if: '!(matrix.skip) && (!startsWith(github.ref, ''refs/tags/''))'
         uses: ./.github/mtime_cache
@@ -442,11 +442,11 @@ jobs:
           github.repository == 'denoland/deno')
         run: |-
           cd target/release
-          shasum -a 256 deno > deno-${{ matrix.arch }}-unknown-linux-gnu.sha256sum
           zip -r deno-${{ matrix.arch }}-unknown-linux-gnu.zip deno
+          shasum -a 256 deno-${{ matrix.arch }}-unknown-linux-gnu.zip > deno-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum
           strip denort
-          shasum -a 256 denort > denort-${{ matrix.arch }}-unknown-linux-gnu.sha256sum
           zip -r denort-${{ matrix.arch }}-unknown-linux-gnu.zip denort
+          shasum -a 256 denort-${{ matrix.arch }}-unknown-linux-gnu.zip > denort-${{ matrix.arch }}-unknown-linux-gnu.zip.sha256sum
           ./deno types > lib.deno.d.ts
       - name: Pre-release (mac)
         if: |-
@@ -461,11 +461,11 @@ jobs:
           echo "Key is $(echo $APPLE_CODESIGN_KEY | base64 -d | wc -c) bytes"
           rcodesign sign target/release/deno --code-signature-flags=runtime --p12-password="$APPLE_CODESIGN_PASSWORD" --p12-file=<(echo $APPLE_CODESIGN_KEY | base64 -d) --entitlements-xml-file=cli/entitlements.plist
           cd target/release
-          shasum -a 256 deno > deno-${{ matrix.arch }}-apple-darwin.sha256sum
           zip -r deno-${{ matrix.arch }}-apple-darwin.zip deno
+          shasum -a 256 deno-${{ matrix.arch }}-apple-darwin.zip > deno-${{ matrix.arch }}-apple-darwin.zip.sha256sum
           strip denort
-          shasum -a 256 denort > denort-${{ matrix.arch }}-apple-darwin.sha256sum
           zip -r denort-${{ matrix.arch }}-apple-darwin.zip denort
+          shasum -a 256 denort-${{ matrix.arch }}-apple-darwin.zip > denort-${{ matrix.arch }}-apple-darwin.zip.sha256sum
       - name: Pre-release (windows)
         if: |-
           !(matrix.skip) && (matrix.os == 'windows' &&
@@ -474,10 +474,10 @@ jobs:
           github.repository == 'denoland/deno')
         shell: pwsh
         run: |-
-          Get-FileHash target/release/deno.exe -Algorithm SHA256 | Format-List > target/release/deno-${{ matrix.arch }}-pc-windows-msvc.sha256sum
           Compress-Archive -CompressionLevel Optimal -Force -Path target/release/deno.exe -DestinationPath target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip
-          Get-FileHash target/release/denort.exe -Algorithm SHA256 | Format-List > target/release/denort-${{ matrix.arch }}-pc-windows-msvc.sha256sum
+          Get-FileHash target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/deno-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum
           Compress-Archive -CompressionLevel Optimal -Force -Path target/release/denort.exe -DestinationPath target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip
+          Get-FileHash target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip -Algorithm SHA256 | Format-List > target/release/denort-${{ matrix.arch }}-pc-windows-msvc.zip.sha256sum
       - name: Upload canary to dl.deno.land
         if: |-
           !(matrix.skip) && (matrix.job == 'test' &&
@@ -652,25 +652,25 @@ jobs:
         with:
           files: |-
             target/release/deno-x86_64-pc-windows-msvc.zip
-            target/release/deno-x86_64-pc-windows-msvc.sha256sum
+            target/release/deno-x86_64-pc-windows-msvc.zip.sha256sum
             target/release/denort-x86_64-pc-windows-msvc.zip
-            target/release/denort-x86_64-pc-windows-msvc.sha256sum
+            target/release/denort-x86_64-pc-windows-msvc.zip.sha256sum
             target/release/deno-x86_64-unknown-linux-gnu.zip
-            target/release/deno-x86_64-unknown-linux-gnu.sha256sum
+            target/release/deno-x86_64-unknown-linux-gnu.zip.sha256sum
             target/release/denort-x86_64-unknown-linux-gnu.zip
-            target/release/denort-x86_64-unknown-linux-gnu.sha256sum
+            target/release/denort-x86_64-unknown-linux-gnu.zip.sha256sum
             target/release/deno-x86_64-apple-darwin.zip
-            target/release/deno-x86_64-apple-darwin.sha256sum
+            target/release/deno-x86_64-apple-darwin.zip.sha256sum
             target/release/denort-x86_64-apple-darwin.zip
-            target/release/denort-x86_64-apple-darwin.sha256sum
+            target/release/denort-x86_64-apple-darwin.zip.sha256sum
             target/release/deno-aarch64-unknown-linux-gnu.zip
-            target/release/deno-aarch64-unknown-linux-gnu.sha256sum
+            target/release/deno-aarch64-unknown-linux-gnu.zip.sha256sum
             target/release/denort-aarch64-unknown-linux-gnu.zip
-            target/release/denort-aarch64-unknown-linux-gnu.sha256sum
+            target/release/denort-aarch64-unknown-linux-gnu.zip.sha256sum
             target/release/deno-aarch64-apple-darwin.zip
-            target/release/deno-aarch64-apple-darwin.sha256sum
+            target/release/deno-aarch64-apple-darwin.zip.sha256sum
             target/release/denort-aarch64-apple-darwin.zip
-            target/release/denort-aarch64-apple-darwin.sha256sum
+            target/release/denort-aarch64-apple-darwin.zip.sha256sum
             target/release/deno_src.tar.gz
             target/release/lib.deno.d.ts
           body_path: target/release/release-notes.md
@@ -685,10 +685,10 @@ jobs:
             !./target/*/*.zip
             !./target/*/*.sha256sum
             !./target/*/*.tar.gz
-          key: '18-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-${{ github.sha }}'
+          key: '23-cargo-target-${{ matrix.os }}-${{ matrix.arch }}-${{ matrix.profile }}-${{ matrix.job }}-${{ github.sha }}'
   publish-canary:
     name: publish canary
-    runs-on: ubuntu-22.04
+    runs-on: ubuntu-24.04
     needs:
       - build
     if: github.repository == 'denoland/deno' && github.ref == 'refs/heads/main'
diff --git a/.github/workflows/promote_to_release.yml b/.github/workflows/promote_to_release.yml
index 3dc15dc730..79fefa6d6c 100644
--- a/.github/workflows/promote_to_release.yml
+++ b/.github/workflows/promote_to_release.yml
@@ -40,7 +40,7 @@ jobs:
           project_id: denoland
 
       - name: Install deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
 
diff --git a/.github/workflows/start_release.yml b/.github/workflows/start_release.yml
index 392551afbe..7c2f149e11 100644
--- a/.github/workflows/start_release.yml
+++ b/.github/workflows/start_release.yml
@@ -34,7 +34,7 @@ jobs:
         uses: actions/checkout@v4
 
       - name: Install deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
 
diff --git a/.github/workflows/version_bump.yml b/.github/workflows/version_bump.yml
index 733abbb024..fd082bca3e 100644
--- a/.github/workflows/version_bump.yml
+++ b/.github/workflows/version_bump.yml
@@ -39,7 +39,7 @@ jobs:
       - uses: dsherret/rust-toolchain-file@v1
 
       - name: Install deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: v1.x
 
diff --git a/.github/workflows/wpt_epoch.yml b/.github/workflows/wpt_epoch.yml
index c3c6277b93..d679498b83 100644
--- a/.github/workflows/wpt_epoch.yml
+++ b/.github/workflows/wpt_epoch.yml
@@ -30,7 +30,7 @@ jobs:
           persist-credentials: false
 
       - name: Setup Deno
-        uses: denoland/setup-deno@v1
+        uses: denoland/setup-deno@v2
         with:
           deno-version: ${{ matrix.deno-version }}
 
diff --git a/Cargo.lock b/Cargo.lock
index 0e6b4fb6ac..8c7b35ca9f 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -769,7 +769,7 @@ dependencies = [
  "http-body-util",
  "hyper 1.4.1",
  "hyper-util",
- "nix 0.26.2",
+ "nix",
  "once_cell",
  "os_pipe",
  "pretty_assertions",
@@ -1154,7 +1154,7 @@ dependencies = [
 
 [[package]]
 name = "deno"
-version = "2.0.0"
+version = "2.0.4"
 dependencies = [
  "anstream",
  "async-trait",
@@ -1188,6 +1188,7 @@ dependencies = [
  "deno_task_shell",
  "deno_terminal 0.2.0",
  "deno_tower_lsp",
+ "dhat",
  "dissimilar",
  "dotenvy",
  "dprint-plugin-json",
@@ -1195,7 +1196,6 @@ dependencies = [
  "dprint-plugin-markdown",
  "dprint-plugin-typescript",
  "env_logger",
- "eszip",
  "fancy-regex",
  "faster-hex",
  "flate2",
@@ -1213,7 +1213,6 @@ dependencies = [
  "lazy-regex",
  "libc",
  "libsui",
- "libuv-sys-lite",
  "libz-sys",
  "log",
  "lsp-types",
@@ -1221,8 +1220,7 @@ dependencies = [
  "markup_fmt",
  "memmem",
  "monch",
- "napi_sym",
- "nix 0.26.2",
+ "nix",
  "node_resolver",
  "notify",
  "once_cell",
@@ -1262,9 +1260,7 @@ dependencies = [
  "walkdir",
  "which 4.4.2",
  "winapi",
- "windows-sys 0.52.0",
  "winres",
- "yoke",
  "zeromq",
  "zip",
  "zstd",
@@ -1283,9 +1279,9 @@ dependencies = [
 
 [[package]]
 name = "deno_ast"
-version = "0.42.2"
+version = "0.43.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b2b9d03b1bbeeecdac54367f075d572131736d06c5be3bc49037855bc5ab1bbb"
+checksum = "48d00b724e06d2081a141ec1155756a0b465d413d8e2a7515221f61d482eb2ee"
 dependencies = [
  "base64 0.21.7",
  "deno_media_type",
@@ -1327,7 +1323,7 @@ dependencies = [
 
 [[package]]
 name = "deno_bench_util"
-version = "0.165.0"
+version = "0.169.0"
 dependencies = [
  "bencher",
  "deno_core",
@@ -1336,31 +1332,33 @@ dependencies = [
 
 [[package]]
 name = "deno_broadcast_channel"
-version = "0.165.0"
+version = "0.169.0"
 dependencies = [
  "async-trait",
  "deno_core",
+ "thiserror",
  "tokio",
  "uuid",
 ]
 
 [[package]]
 name = "deno_cache"
-version = "0.103.0"
+version = "0.107.0"
 dependencies = [
  "async-trait",
  "deno_core",
  "rusqlite",
  "serde",
  "sha2",
+ "thiserror",
  "tokio",
 ]
 
 [[package]]
 name = "deno_cache_dir"
-version = "0.13.0"
+version = "0.13.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "186a102b13b4512841f5f40784cd25822042d22954afe3b5b070d406d15eb4f2"
+checksum = "08c1f52170cd7715f8006da54cde1444863a0d6fbd9c11d037a737db2dec8e22"
 dependencies = [
  "base32",
  "deno_media_type",
@@ -1378,19 +1376,20 @@ dependencies = [
 
 [[package]]
 name = "deno_canvas"
-version = "0.40.0"
+version = "0.44.0"
 dependencies = [
  "deno_core",
  "deno_webgpu",
  "image",
  "serde",
+ "thiserror",
 ]
 
 [[package]]
 name = "deno_config"
-version = "0.37.1"
+version = "0.37.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3cb7a1723676fba5964f8d7441d8b53748f9e74d6d4241be7de9730da021859a"
+checksum = "5900bfb37538d83b19ba0b157cdc785770e38422ee4632411e3bd3d90ac0f537"
 dependencies = [
  "anyhow",
  "deno_package_json",
@@ -1412,16 +1411,16 @@ dependencies = [
 
 [[package]]
 name = "deno_console"
-version = "0.171.0"
+version = "0.175.0"
 dependencies = [
  "deno_core",
 ]
 
 [[package]]
 name = "deno_core"
-version = "0.311.0"
+version = "0.316.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5e09bd55da542fa1fde753aff617c355b5d782e763ab2a19e4371a56d7844cac"
+checksum = "94f68061c88ced959c6b0417f0f0d0b3dbeaeb18013b55f86c505e9fba705cf8"
 dependencies = [
  "anyhow",
  "bincode",
@@ -1434,7 +1433,7 @@ dependencies = [
  "deno_unsync",
  "futures",
  "libc",
- "memoffset 0.9.1",
+ "memoffset",
  "parking_lot",
  "percent-encoding",
  "pin-project",
@@ -1457,19 +1456,20 @@ checksum = "a13951ea98c0a4c372f162d669193b4c9d991512de9f2381dd161027f34b26b1"
 
 [[package]]
 name = "deno_cron"
-version = "0.51.0"
+version = "0.55.0"
 dependencies = [
  "anyhow",
  "async-trait",
  "chrono",
  "deno_core",
  "saffron",
+ "thiserror",
  "tokio",
 ]
 
 [[package]]
 name = "deno_crypto"
-version = "0.185.0"
+version = "0.189.0"
 dependencies = [
  "aes",
  "aes-gcm",
@@ -1498,15 +1498,17 @@ dependencies = [
  "sha2",
  "signature",
  "spki",
+ "thiserror",
+ "tokio",
  "uuid",
  "x25519-dalek",
 ]
 
 [[package]]
 name = "deno_doc"
-version = "0.153.0"
+version = "0.156.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6925db7ad16bee4bdcb7e654d2475e2fbd5e1d7dd4c6ee5f030ee858b4a2a8ee"
+checksum = "2585b98d6ad76dae30bf2d7b6d71b8363cae041158b8780d14a2f4fe17590a61"
 dependencies = [
  "anyhow",
  "cfg-if",
@@ -1523,23 +1525,13 @@ dependencies = [
  "regex",
  "serde",
  "serde_json",
+ "syntect",
  "termcolor",
- "tree-sitter-bash",
- "tree-sitter-css",
- "tree-sitter-highlight",
- "tree-sitter-html",
- "tree-sitter-javascript",
- "tree-sitter-json",
- "tree-sitter-md",
- "tree-sitter-regex",
- "tree-sitter-rust",
- "tree-sitter-typescript",
- "tree-sitter-xml",
 ]
 
 [[package]]
 name = "deno_fetch"
-version = "0.195.0"
+version = "0.199.0"
 dependencies = [
  "base64 0.21.7",
  "bytes",
@@ -1560,6 +1552,7 @@ dependencies = [
  "rustls-webpki",
  "serde",
  "serde_json",
+ "thiserror",
  "tokio",
  "tokio-rustls",
  "tokio-socks",
@@ -1571,7 +1564,7 @@ dependencies = [
 
 [[package]]
 name = "deno_ffi"
-version = "0.158.0"
+version = "0.162.0"
 dependencies = [
  "deno_core",
  "deno_permissions",
@@ -1580,15 +1573,18 @@ dependencies = [
  "libffi",
  "libffi-sys",
  "log",
+ "num-bigint",
  "serde",
  "serde-value",
  "serde_json",
+ "thiserror",
+ "tokio",
  "winapi",
 ]
 
 [[package]]
 name = "deno_fs"
-version = "0.81.0"
+version = "0.85.0"
 dependencies = [
  "async-trait",
  "base32",
@@ -1599,19 +1595,20 @@ dependencies = [
  "filetime",
  "junction",
  "libc",
- "nix 0.26.2",
+ "nix",
  "rand",
  "rayon",
  "serde",
+ "thiserror",
  "winapi",
  "windows-sys 0.52.0",
 ]
 
 [[package]]
 name = "deno_graph"
-version = "0.83.3"
+version = "0.84.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "77163c46755676d8f793fc19e365537ba660a8db173cd1e02d21eb010c0b3cef"
+checksum = "cd4f4a14aa069087be41c2998077b0453f0191747898f96e6343f700abfc2c18"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -1638,7 +1635,7 @@ dependencies = [
 
 [[package]]
 name = "deno_http"
-version = "0.169.0"
+version = "0.173.0"
 dependencies = [
  "async-compression",
  "async-trait",
@@ -1677,7 +1674,7 @@ dependencies = [
 
 [[package]]
 name = "deno_io"
-version = "0.81.0"
+version = "0.85.0"
 dependencies = [
  "async-trait",
  "deno_core",
@@ -1698,7 +1695,7 @@ dependencies = [
 
 [[package]]
 name = "deno_kv"
-version = "0.79.0"
+version = "0.83.0"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -1723,14 +1720,15 @@ dependencies = [
  "rand",
  "rusqlite",
  "serde",
+ "thiserror",
  "url",
 ]
 
 [[package]]
 name = "deno_lint"
-version = "0.67.0"
+version = "0.68.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "871b60e32bfb6c110cbb9b0688dbf048f81e5d347fe4ce5a42239263de9dd938"
+checksum = "bb994e6d1b18223df0a756c7948143b35682941d615edffef60d5b38822f38ac"
 dependencies = [
  "anyhow",
  "deno_ast",
@@ -1758,9 +1756,9 @@ dependencies = [
 
 [[package]]
 name = "deno_media_type"
-version = "0.1.4"
+version = "0.2.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a8978229b82552bf8457a0125aa20863f023619cfc21ebb007b1e571d68fd85b"
+checksum = "7fcf552fbdedbe81c89705349d7d2485c7051382b000dfddbdbf7fc25931cf83"
 dependencies = [
  "data-url",
  "serde",
@@ -1769,11 +1767,17 @@ dependencies = [
 
 [[package]]
 name = "deno_napi"
-version = "0.102.0"
+version = "0.106.0"
 dependencies = [
  "deno_core",
  "deno_permissions",
+ "libc",
  "libloading 0.7.4",
+ "libuv-sys-lite",
+ "log",
+ "napi_sym",
+ "thiserror",
+ "windows-sys 0.52.0",
 ]
 
 [[package]]
@@ -1791,7 +1795,7 @@ dependencies = [
 
 [[package]]
 name = "deno_net"
-version = "0.163.0"
+version = "0.167.0"
 dependencies = [
  "deno_core",
  "deno_permissions",
@@ -1800,6 +1804,7 @@ dependencies = [
  "rustls-tokio-stream",
  "serde",
  "socket2",
+ "thiserror",
  "tokio",
  "trust-dns-proto",
  "trust-dns-resolver",
@@ -1807,7 +1812,7 @@ dependencies = [
 
 [[package]]
 name = "deno_node"
-version = "0.108.0"
+version = "0.112.0"
 dependencies = [
  "aead-gcm-stream",
  "aes",
@@ -1897,9 +1902,9 @@ dependencies = [
 
 [[package]]
 name = "deno_npm"
-version = "0.25.3"
+version = "0.25.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8050bcc2513046cbc0134ae1bc0f3b251a58b95012f3b81e0ea09a7f069c301b"
+checksum = "e6b4dc4a9f1cff63d5638e7d93042f24f46300d1cc77b86f3caaa699a7ddccf7"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -1916,9 +1921,9 @@ dependencies = [
 
 [[package]]
 name = "deno_ops"
-version = "0.187.0"
+version = "0.192.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e040fd4def8a67538fe38c9955fd970efc9f44284bd69d44f8992a456afd665d"
+checksum = "bdb7096887508456349d7e7e09e326d157d4dba46ef1f5849bc544592ea3042a"
 dependencies = [
  "proc-macro-rules",
  "proc-macro2",
@@ -1956,7 +1961,7 @@ dependencies = [
 
 [[package]]
 name = "deno_permissions"
-version = "0.31.0"
+version = "0.35.0"
 dependencies = [
  "deno_core",
  "deno_path_util",
@@ -1973,7 +1978,7 @@ dependencies = [
 
 [[package]]
 name = "deno_resolver"
-version = "0.3.0"
+version = "0.7.0"
 dependencies = [
  "anyhow",
  "base32",
@@ -1989,8 +1994,9 @@ dependencies = [
 
 [[package]]
 name = "deno_runtime"
-version = "0.180.0"
+version = "0.184.0"
 dependencies = [
+ "color-print",
  "deno_ast",
  "deno_broadcast_channel",
  "deno_cache",
@@ -2030,7 +2036,7 @@ dependencies = [
  "libc",
  "log",
  "netif",
- "nix 0.26.2",
+ "nix",
  "node_resolver",
  "notify",
  "ntapi",
@@ -2038,11 +2044,13 @@ dependencies = [
  "percent-encoding",
  "regex",
  "rustyline",
+ "same-file",
  "serde",
  "signal-hook",
  "signal-hook-registry",
  "tempfile",
  "test_server",
+ "thiserror",
  "tokio",
  "tokio-metrics",
  "twox-hash",
@@ -2054,9 +2062,9 @@ dependencies = [
 
 [[package]]
 name = "deno_semver"
-version = "0.5.14"
+version = "0.5.16"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "670fec7ef309384e23c2a90ac5d2d9d91a776d225306c75f5cdd28cf6cc8a59f"
+checksum = "c957c6a57c38b7dde2315df0da0ec228911e56a74f185b108a488d0401841a67"
 dependencies = [
  "monch",
  "once_cell",
@@ -2104,7 +2112,7 @@ dependencies = [
 
 [[package]]
 name = "deno_tls"
-version = "0.158.0"
+version = "0.162.0"
 dependencies = [
  "deno_core",
  "deno_native_certs",
@@ -2113,6 +2121,7 @@ dependencies = [
  "rustls-tokio-stream",
  "rustls-webpki",
  "serde",
+ "thiserror",
  "tokio",
  "webpki-roots",
 ]
@@ -2152,18 +2161,19 @@ dependencies = [
 
 [[package]]
 name = "deno_url"
-version = "0.171.0"
+version = "0.175.0"
 dependencies = [
  "deno_bench_util",
  "deno_console",
  "deno_core",
  "deno_webidl",
+ "thiserror",
  "urlpattern",
 ]
 
 [[package]]
 name = "deno_web"
-version = "0.202.0"
+version = "0.206.0"
 dependencies = [
  "async-trait",
  "base64-simd 0.8.0",
@@ -2178,17 +2188,19 @@ dependencies = [
  "flate2",
  "futures",
  "serde",
+ "thiserror",
  "tokio",
  "uuid",
 ]
 
 [[package]]
 name = "deno_webgpu"
-version = "0.138.0"
+version = "0.142.0"
 dependencies = [
  "deno_core",
  "raw-window-handle",
  "serde",
+ "thiserror",
  "tokio",
  "wgpu-core",
  "wgpu-types",
@@ -2196,7 +2208,7 @@ dependencies = [
 
 [[package]]
 name = "deno_webidl"
-version = "0.171.0"
+version = "0.175.0"
 dependencies = [
  "deno_bench_util",
  "deno_core",
@@ -2204,7 +2216,7 @@ dependencies = [
 
 [[package]]
 name = "deno_websocket"
-version = "0.176.0"
+version = "0.180.0"
 dependencies = [
  "bytes",
  "deno_core",
@@ -2220,16 +2232,18 @@ dependencies = [
  "once_cell",
  "rustls-tokio-stream",
  "serde",
+ "thiserror",
  "tokio",
 ]
 
 [[package]]
 name = "deno_webstorage"
-version = "0.166.0"
+version = "0.170.0"
 dependencies = [
  "deno_core",
  "deno_web",
  "rusqlite",
+ "thiserror",
 ]
 
 [[package]]
@@ -2415,6 +2429,22 @@ version = "1.4.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b6e854126756c496b8c81dec88f9a706b15b875c5849d4097a3854476b9fdf94"
 
+[[package]]
+name = "dhat"
+version = "0.3.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "98cd11d84628e233de0ce467de10b8633f4ddaecafadefc86e13b84b8739b827"
+dependencies = [
+ "backtrace",
+ "lazy_static",
+ "mintex",
+ "parking_lot",
+ "rustc-hash 1.1.0",
+ "serde",
+ "serde_json",
+ "thousands",
+]
+
 [[package]]
 name = "diff"
 version = "0.1.13"
@@ -2536,9 +2566,9 @@ dependencies = [
 
 [[package]]
 name = "dprint-plugin-json"
-version = "0.19.3"
+version = "0.19.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a19f4a9f2f548b2098b8ec597d7bb40af133b6e9a3187c1d3c4caa101b8c93c3"
+checksum = "57f91e594559b450b7c5d6a0ba9f3f9fe951c1ea371168f7c95973da3fdbd85a"
 dependencies = [
  "anyhow",
  "dprint-core",
@@ -2550,9 +2580,9 @@ dependencies = [
 
 [[package]]
 name = "dprint-plugin-jupyter"
-version = "0.1.3"
+version = "0.1.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c67b0e54b552a4775c221b44ed33be918c400bd8041d1f044f947fbb01025cc0"
+checksum = "d0d20684e37b3824e2bc917cfcb14e2cdf88398eef507335d839cbd78172bfee"
 dependencies = [
  "anyhow",
  "dprint-core",
@@ -2578,9 +2608,9 @@ dependencies = [
 
 [[package]]
 name = "dprint-plugin-typescript"
-version = "0.93.0"
+version = "0.93.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e9308d98b923b7c0335c2ee1560199e3f2321b1be82803107b4ba4ed5dac46cc"
+checksum = "5abfd78fe3cde4f5a6699d65f760c8d44da130cf446b6f80a7a9bc6580e156ab"
 dependencies = [
  "anyhow",
  "deno_ast",
@@ -2864,29 +2894,6 @@ version = "1.0.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "31ae425815400e5ed474178a7a22e275a9687086a12ca63ec793ff292d8fdae8"
 
-[[package]]
-name = "eszip"
-version = "0.79.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8eb55c89bdde75a3826a79d49c9d847623ae7fbdb2695b542982982da990d33e"
-dependencies = [
- "anyhow",
- "async-trait",
- "base64 0.21.7",
- "deno_ast",
- "deno_graph",
- "deno_npm",
- "deno_semver",
- "futures",
- "hashlink 0.8.4",
- "indexmap",
- "serde",
- "serde_json",
- "sha2",
- "thiserror",
- "url",
-]
-
 [[package]]
 name = "fallible-iterator"
 version = "0.3.0"
@@ -3498,15 +3505,6 @@ dependencies = [
  "allocator-api2",
 ]
 
-[[package]]
-name = "hashlink"
-version = "0.8.4"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e8094feaf31ff591f651a2664fb9cfd92bba7a60ce3197265e9482ebe753c8f7"
-dependencies = [
- "hashbrown",
-]
-
 [[package]]
 name = "hashlink"
 version = "0.9.1"
@@ -4007,9 +4005,9 @@ dependencies = [
 
 [[package]]
 name = "jsonc-parser"
-version = "0.23.0"
+version = "0.26.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7725c320caac8c21d8228c1d055af27a995d371f78cc763073d3e068323641b5"
+checksum = "b558af6b49fd918e970471374e7a798b2c9bbcda624a210ffa3901ee5614bc8e"
 dependencies = [
  "serde_json",
 ]
@@ -4300,9 +4298,9 @@ dependencies = [
 
 [[package]]
 name = "malva"
-version = "0.10.1"
+version = "0.11.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "484beda6e5d775ed06a8ec0fce79e51d39f49d834ed2a29da3f437079321804f"
+checksum = "1c67b97ed99f56b86fa3c010843441f1fcdb71884bab96b8551bb3d1e7c6d529"
 dependencies = [
  "aho-corasick",
  "itertools 0.13.0",
@@ -4313,9 +4311,9 @@ dependencies = [
 
 [[package]]
 name = "markup_fmt"
-version = "0.13.1"
+version = "0.15.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9dab5ae899659fbe5c8835b2c8ca8d3e357974a3e454138925b404004973361f"
+checksum = "ebae65c91eab3d42231232bf48107f351e5a8d511454927218c53aeb68bbdb6f"
 dependencies = [
  "aho-corasick",
  "css_dataset",
@@ -4370,15 +4368,6 @@ version = "0.1.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "a64a92489e2744ce060c349162be1c5f33c6969234104dbd99ddb5feb08b8c15"
 
-[[package]]
-name = "memoffset"
-version = "0.7.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5de893c32cde5f383baa4c04c5d6dbdd735cfd4a794b0debdb2bb1b421da5ff4"
-dependencies = [
- "autocfg",
-]
-
 [[package]]
 name = "memoffset"
 version = "0.9.1"
@@ -4425,6 +4414,12 @@ dependencies = [
  "simd-adler32",
 ]
 
+[[package]]
+name = "mintex"
+version = "0.1.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9bec4598fddb13cc7b528819e697852653252b760f1228b7642679bf2ff2cd07"
+
 [[package]]
 name = "mio"
 version = "0.8.11"
@@ -4488,7 +4483,7 @@ dependencies = [
 
 [[package]]
 name = "napi_sym"
-version = "0.101.0"
+version = "0.105.0"
 dependencies = [
  "quote",
  "serde",
@@ -4530,20 +4525,6 @@ dependencies = [
  "smallvec",
 ]
 
-[[package]]
-name = "nix"
-version = "0.26.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bfdda3d196821d6af13126e40375cdf7da646a96114af134d5f417a9a1dc8e1a"
-dependencies = [
- "bitflags 1.3.2",
- "cfg-if",
- "libc",
- "memoffset 0.7.1",
- "pin-utils",
- "static_assertions",
-]
-
 [[package]]
 name = "nix"
 version = "0.27.1"
@@ -4557,7 +4538,7 @@ dependencies = [
 
 [[package]]
 name = "node_resolver"
-version = "0.10.0"
+version = "0.14.0"
 dependencies = [
  "anyhow",
  "async-trait",
@@ -4733,6 +4714,28 @@ version = "1.19.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "3fdb12b2476b595f9358c5161aa467c2438859caa136dec86c26fdd2efe17b92"
 
+[[package]]
+name = "onig"
+version = "6.4.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8c4b31c8722ad9171c6d77d3557db078cab2bd50afcc9d09c8b315c59df8ca4f"
+dependencies = [
+ "bitflags 1.3.2",
+ "libc",
+ "once_cell",
+ "onig_sys",
+]
+
+[[package]]
+name = "onig_sys"
+version = "69.8.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7b829e3d7e9cc74c7e315ee8edb185bf4190da5acde74afd7fc59c35b1f086e7"
+dependencies = [
+ "cc",
+ "pkg-config",
+]
+
 [[package]]
 name = "opaque-debug"
 version = "0.3.1"
@@ -5721,7 +5724,7 @@ checksum = "32a58fa8a7ccff2aec4f39cc45bf5f985cec7125ab271cf681c279fd00192b49"
 dependencies = [
  "countme",
  "hashbrown",
- "memoffset 0.9.1",
+ "memoffset",
  "rustc-hash 1.1.0",
  "text-size",
 ]
@@ -5779,7 +5782,7 @@ dependencies = [
  "bitflags 2.6.0",
  "fallible-iterator",
  "fallible-streaming-iterator",
- "hashlink 0.9.1",
+ "hashlink",
  "libsqlite3-sys",
  "smallvec",
 ]
@@ -5929,7 +5932,7 @@ dependencies = [
  "libc",
  "log",
  "memchr",
- "nix 0.27.1",
+ "nix",
  "radix_trie",
  "unicode-segmentation",
  "unicode-width",
@@ -6166,9 +6169,9 @@ dependencies = [
 
 [[package]]
 name = "serde_v8"
-version = "0.220.0"
+version = "0.225.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6e7a65d91d79acc82aa229aeb084f4a39bda269069bc1520df40f679495388e4"
+checksum = "ce4b71200ef49a9e629edaea3d13fc98c25ede07e1496558df7f09354e37976f"
 dependencies = [
  "num-bigint",
  "serde",
@@ -7021,6 +7024,26 @@ dependencies = [
  "syn 2.0.72",
 ]
 
+[[package]]
+name = "syntect"
+version = "5.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "874dcfa363995604333cf947ae9f751ca3af4522c60886774c4963943b4746b1"
+dependencies = [
+ "bincode",
+ "bitflags 1.3.2",
+ "flate2",
+ "fnv",
+ "once_cell",
+ "onig",
+ "regex-syntax",
+ "serde",
+ "serde_derive",
+ "serde_json",
+ "thiserror",
+ "walkdir",
+]
+
 [[package]]
 name = "tap"
 version = "1.0.1"
@@ -7112,7 +7135,7 @@ dependencies = [
  "libc",
  "lsp-types",
  "monch",
- "nix 0.26.2",
+ "nix",
  "once_cell",
  "os_pipe",
  "parking_lot",
@@ -7153,24 +7176,30 @@ dependencies = [
 
 [[package]]
 name = "thiserror"
-version = "1.0.61"
+version = "1.0.64"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c546c80d6be4bc6a00c0f01730c08df82eaa7a7a61f11d656526506112cc1709"
+checksum = "d50af8abc119fb8bb6dbabcfa89656f46f84aa0ac7688088608076ad2b459a84"
 dependencies = [
  "thiserror-impl",
 ]
 
 [[package]]
 name = "thiserror-impl"
-version = "1.0.61"
+version = "1.0.64"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "46c3384250002a6d5af4d114f2845d37b57521033f30d5c3f46c4d70e1197533"
+checksum = "08904e7672f5eb876eaaf87e0ce17857500934f4981c4a0ab2b4aa98baac7fc3"
 dependencies = [
  "proc-macro2",
  "quote",
  "syn 2.0.72",
 ]
 
+[[package]]
+name = "thousands"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3bf63baf9f5039dadc247375c29eb13706706cfde997d0330d05aa63a77d8820"
+
 [[package]]
 name = "thread_local"
 version = "1.1.8"
@@ -7452,128 +7481,6 @@ dependencies = [
  "once_cell",
 ]
 
-[[package]]
-name = "tree-sitter"
-version = "0.22.6"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "df7cc499ceadd4dcdf7ec6d4cbc34ece92c3fa07821e287aedecd4416c516dca"
-dependencies = [
- "cc",
- "regex",
-]
-
-[[package]]
-name = "tree-sitter-bash"
-version = "0.21.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b5244703ad2e08a616d859a0557d7aa290adcd5e0990188a692e628ffe9dce40"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-css"
-version = "0.21.1"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5e08e324b1cf60fd3291774b49724c66de2ce8fcf4d358d0b4b82e37b41b1c9b"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-highlight"
-version = "0.22.6"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "eaca0fe34fa96eec6aaa8e63308dbe1bafe65a6317487c287f93938959b21907"
-dependencies = [
- "lazy_static",
- "regex",
- "thiserror",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-html"
-version = "0.20.4"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8766b5ad3721517f8259e6394aefda9c686aebf7a8c74ab8624f2c3b46902fd5"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-javascript"
-version = "0.21.4"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8710a71bc6779e33811a8067bdda3ed08bed1733296ff915e44faf60f8c533d7"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-json"
-version = "0.21.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5b737dcb73c35d74b7d64a5f3dde158113c86a012bf3cee2bfdf2150d23b05db"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-md"
-version = "0.2.3"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "d9c3cfd068f2527250bbd8ff407431164e12b17863e7eafb76e311dd3f96965a"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-regex"
-version = "0.21.0"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5ff1286fe9651b2797484839ffa37aa76c8618d4ccb6836d7e31765dfd60c0d5"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-rust"
-version = "0.21.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "277690f420bf90741dea984f3da038ace46c4fe6047cba57a66822226cde1c93"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-typescript"
-version = "0.21.2"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "ecb35d98a688378e56c18c9c159824fd16f730ccbea19aacf4f206e5d5438ed9"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
-[[package]]
-name = "tree-sitter-xml"
-version = "0.6.4"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "65c3a1b08e9842143f84fde1a18ac40ee77ca80a80b14077e4ca67a3b4808b8b"
-dependencies = [
- "cc",
- "tree-sitter",
-]
-
 [[package]]
 name = "triomphe"
 version = "0.1.13"
diff --git a/Cargo.toml b/Cargo.toml
index 1128c64e34..f57563e0b8 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -5,7 +5,6 @@ resolver = "2"
 members = [
   "bench_util",
   "cli",
-  "cli/napi/sym",
   "ext/broadcast_channel",
   "ext/cache",
   "ext/canvas",
@@ -19,6 +18,7 @@ members = [
   "ext/io",
   "ext/kv",
   "ext/napi",
+  "ext/napi/sym",
   "ext/net",
   "ext/node",
   "ext/url",
@@ -45,19 +45,19 @@ license = "MIT"
 repository = "https://github.com/denoland/deno"
 
 [workspace.dependencies]
-deno_ast = { version = "=0.42.2", features = ["transpiling"] }
-deno_core = { version = "0.311.0" }
+deno_ast = { version = "=0.43.3", features = ["transpiling"] }
+deno_core = { version = "0.316.0" }
 
-deno_bench_util = { version = "0.165.0", path = "./bench_util" }
+deno_bench_util = { version = "0.169.0", path = "./bench_util" }
 deno_lockfile = "=0.23.1"
-deno_media_type = { version = "0.1.4", features = ["module_specifier"] }
-deno_npm = "=0.25.3"
+deno_media_type = { version = "0.2.0", features = ["module_specifier"] }
+deno_npm = "=0.25.4"
 deno_path_util = "=0.2.1"
-deno_permissions = { version = "0.31.0", path = "./runtime/permissions" }
-deno_runtime = { version = "0.180.0", path = "./runtime" }
-deno_semver = "=0.5.14"
+deno_permissions = { version = "0.35.0", path = "./runtime/permissions" }
+deno_runtime = { version = "0.184.0", path = "./runtime" }
+deno_semver = "=0.5.16"
 deno_terminal = "0.2.0"
-napi_sym = { version = "0.101.0", path = "./cli/napi/sym" }
+napi_sym = { version = "0.105.0", path = "./ext/napi/sym" }
 test_util = { package = "test_server", path = "./tests/util/server" }
 
 denokv_proto = "0.8.1"
@@ -66,32 +66,32 @@ denokv_remote = "0.8.1"
 denokv_sqlite = { default-features = false, version = "0.8.2" }
 
 # exts
-deno_broadcast_channel = { version = "0.165.0", path = "./ext/broadcast_channel" }
-deno_cache = { version = "0.103.0", path = "./ext/cache" }
-deno_canvas = { version = "0.40.0", path = "./ext/canvas" }
-deno_console = { version = "0.171.0", path = "./ext/console" }
-deno_cron = { version = "0.51.0", path = "./ext/cron" }
-deno_crypto = { version = "0.185.0", path = "./ext/crypto" }
-deno_fetch = { version = "0.195.0", path = "./ext/fetch" }
-deno_ffi = { version = "0.158.0", path = "./ext/ffi" }
-deno_fs = { version = "0.81.0", path = "./ext/fs" }
-deno_http = { version = "0.169.0", path = "./ext/http" }
-deno_io = { version = "0.81.0", path = "./ext/io" }
-deno_kv = { version = "0.79.0", path = "./ext/kv" }
-deno_napi = { version = "0.102.0", path = "./ext/napi" }
-deno_net = { version = "0.163.0", path = "./ext/net" }
-deno_node = { version = "0.108.0", path = "./ext/node" }
-deno_tls = { version = "0.158.0", path = "./ext/tls" }
-deno_url = { version = "0.171.0", path = "./ext/url" }
-deno_web = { version = "0.202.0", path = "./ext/web" }
-deno_webgpu = { version = "0.138.0", path = "./ext/webgpu" }
-deno_webidl = { version = "0.171.0", path = "./ext/webidl" }
-deno_websocket = { version = "0.176.0", path = "./ext/websocket" }
-deno_webstorage = { version = "0.166.0", path = "./ext/webstorage" }
+deno_broadcast_channel = { version = "0.169.0", path = "./ext/broadcast_channel" }
+deno_cache = { version = "0.107.0", path = "./ext/cache" }
+deno_canvas = { version = "0.44.0", path = "./ext/canvas" }
+deno_console = { version = "0.175.0", path = "./ext/console" }
+deno_cron = { version = "0.55.0", path = "./ext/cron" }
+deno_crypto = { version = "0.189.0", path = "./ext/crypto" }
+deno_fetch = { version = "0.199.0", path = "./ext/fetch" }
+deno_ffi = { version = "0.162.0", path = "./ext/ffi" }
+deno_fs = { version = "0.85.0", path = "./ext/fs" }
+deno_http = { version = "0.173.0", path = "./ext/http" }
+deno_io = { version = "0.85.0", path = "./ext/io" }
+deno_kv = { version = "0.83.0", path = "./ext/kv" }
+deno_napi = { version = "0.106.0", path = "./ext/napi" }
+deno_net = { version = "0.167.0", path = "./ext/net" }
+deno_node = { version = "0.112.0", path = "./ext/node" }
+deno_tls = { version = "0.162.0", path = "./ext/tls" }
+deno_url = { version = "0.175.0", path = "./ext/url" }
+deno_web = { version = "0.206.0", path = "./ext/web" }
+deno_webgpu = { version = "0.142.0", path = "./ext/webgpu" }
+deno_webidl = { version = "0.175.0", path = "./ext/webidl" }
+deno_websocket = { version = "0.180.0", path = "./ext/websocket" }
+deno_webstorage = { version = "0.170.0", path = "./ext/webstorage" }
 
 # resolvers
-deno_resolver = { version = "0.3.0", path = "./resolvers/deno" }
-node_resolver = { version = "0.10.0", path = "./resolvers/node" }
+deno_resolver = { version = "0.7.0", path = "./resolvers/deno" }
+node_resolver = { version = "0.14.0", path = "./resolvers/node" }
 
 aes = "=0.8.3"
 anyhow = "1.0.57"
@@ -106,11 +106,12 @@ cbc = { version = "=0.1.2", features = ["alloc"] }
 # Note: Do not use the "clock" feature of chrono, as it links us to CoreFoundation on macOS.
 #       Instead use util::time::utc_now()
 chrono = { version = "0.4", default-features = false, features = ["std", "serde"] }
+color-print = "0.3.5"
 console_static_text = "=0.8.1"
 dashmap = "5.5.3"
 data-encoding = "2.3.3"
 data-url = "=0.3.0"
-deno_cache_dir = "=0.13.0"
+deno_cache_dir = "=0.13.2"
 deno_package_json = { version = "0.1.2", default-features = false }
 dlopen2 = "0.6.1"
 ecb = "=0.1.2"
@@ -136,7 +137,7 @@ hyper-util = { version = "=0.1.7", features = ["tokio", "client", "client-legacy
 hyper_v014 = { package = "hyper", version = "0.14.26", features = ["runtime", "http1"] }
 indexmap = { version = "2", features = ["serde"] }
 ipnet = "2.3"
-jsonc-parser = { version = "=0.23.0", features = ["serde"] }
+jsonc-parser = { version = "=0.26.2", features = ["serde"] }
 lazy-regex = "3"
 libc = "0.2.126"
 libz-sys = { version = "1.1.20", default-features = false }
@@ -186,7 +187,7 @@ tar = "=0.4.40"
 tempfile = "3.4.0"
 termcolor = "1.1.3"
 thiserror = "1.0.61"
-tokio = { version = "=1.36.0", features = ["full"] }
+tokio = { version = "1.36.0", features = ["full"] }
 tokio-metrics = { version = "0.3.0", features = ["rt"] }
 tokio-rustls = { version = "0.26.0", default-features = false, features = ["ring", "tls12"] }
 tokio-socks = "0.5.1"
@@ -220,7 +221,7 @@ quote = "1"
 syn = { version = "2", features = ["full", "extra-traits"] }
 
 # unix
-nix = "=0.26.2"
+nix = "=0.27.1"
 
 # windows deps
 junction = "=0.2.0"
diff --git a/README.md b/README.md
index 102319f4f2..19d4fa8a12 100644
--- a/README.md
+++ b/README.md
@@ -46,6 +46,12 @@ brew install deno
 choco install deno
 ```
 
+[WinGet](https://winstall.app/apps/DenoLand.Deno) (Windows):
+
+```powershell
+winget install --id=DenoLand.Deno
+```
+
 ### Build and install from source
 
 Complete instructions for building Deno from source can be found in the manual
diff --git a/Releases.md b/Releases.md
index 80fdc7fb8d..a183e01ecd 100644
--- a/Releases.md
+++ b/Releases.md
@@ -6,6 +6,147 @@ https://github.com/denoland/deno/releases
 We also have one-line install commands at:
 https://github.com/denoland/deno_install
 
+### 2.0.4 / 2024.10.29
+
+- Revert "fix(ext/node): fix dns.lookup result ordering (#26264)" (#26621)
+- Revert "fix(ext/node): use primordials in `ext/node/polyfills/https.ts`
+  (#26323)" (#26613)
+- feat(lsp): "typescript.preferences.preferTypeOnlyAutoImports" setting (#26546)
+- fix(check): expose more globals from @types/node (#26603)
+- fix(check): ignore resolving `jsxImportSource` when jsx is not used in graph
+  (#26548)
+- fix(cli): Make --watcher CLEAR_SCREEN clear scrollback buffer as well as
+  visible screen (#25997)
+- fix(compile): regression handling redirects (#26586)
+- fix(ext/napi): export dynamic symbols list for {Free,Open}BSD (#26605)
+- fix(ext/node): add path to `fs.stat` and `fs.statSync` error (#26037)
+- fix(ext/node): compatibility with {Free,Open}BSD (#26604)
+- fix(ext/node): use primordials in
+  ext\node\polyfills\internal\crypto\_randomInt.ts (#26534)
+- fix(install): cache json exports of JSR packages (#26552)
+- fix(install): regression - do not panic when config file contains \r\n
+  newlines (#26547)
+- fix(lsp): make missing import action fix infallible (#26539)
+- fix(npm): match npm bearer token generation (#26544)
+- fix(upgrade): stop running `deno lsp` processes on windows before attempting
+  to replace executable (#26542)
+- fix(watch): don't panic on invalid file specifiers (#26577)
+- fix: do not panic when failing to write to http cache (#26591)
+- fix: provide hints in terminal errors for Node.js globals (#26610)
+- fix: report exceptions from nextTick (#26579)
+- fix: support watch flag to enable watching other files than the main module on
+  serve subcommand (#26622)
+- perf: pass transpiled module to deno_core as known string (#26555)
+
+### 2.0.3 / 2024.10.25
+
+- feat(lsp): interactive inlay hints (#26382)
+- fix: support node-api in denort (#26389)
+- fix(check): support `--frozen` on deno check (#26479)
+- fix(cli): increase size of blocking task threadpool on windows (#26465)
+- fix(config): schemas for lint rule and tag autocompletion (#26515)
+- fix(ext/console): ignore casing for named colors in css parsing (#26466)
+- fix(ext/ffi): return u64/i64 as bigints from nonblocking ffi calls (#26486)
+- fix(ext/node): cancel pending ipc writes on channel close (#26504)
+- fix(ext/node): map `ERROR_INVALID_NAME` to `ENOENT` on windows (#26475)
+- fix(ext/node): only set our end of child process pipe to nonblocking mode
+  (#26495)
+- fix(ext/node): properly map reparse point error in readlink (#26375)
+- fix(ext/node): refactor http.ServerResponse into function class (#26210)
+- fix(ext/node): stub HTTPParser internal binding (#26401)
+- fix(ext/node): use primordials in `ext/node/polyfills/https.ts` (#26323)
+- fix(fmt): --ext flag requires to pass files (#26525)
+- fix(fmt): upgrade formatters (#26469)
+- fix(help): missing package specifier (#26380)
+- fix(info): resolve workspace member mappings (#26350)
+- fix(install): better json editing (#26450)
+- fix(install): cache all exports of JSR packages listed in `deno.json` (#26501)
+- fix(install): cache type only module deps in `deno install` (#26497)
+- fix(install): don't cache json exports of JSR packages (for now) (#26530)
+- fix(install): update lockfile when using package.json (#26458)
+- fix(lsp): import-map-remap quickfix for type imports (#26454)
+- fix(node/util): support array formats in `styleText` (#26507)
+- fix(node:tls): set TLSSocket.alpnProtocol for client connections (#26476)
+- fix(npm): ensure scoped package name is encoded in URLs (#26390)
+- fix(npm): support version ranges with && or comma (#26453)
+- fix: `.npmrc` settings not being passed to install/add command (#26473)
+- fix: add 'fmt-component' to unstable features in schema file (#26526)
+- fix: share inotify fd across watchers (#26200)
+- fix: unpin tokio version (#26457)
+- perf(compile): pass module source data from binary directly to v8 (#26494)
+- perf: avoid multiple calls to runMicrotask (#26378)
+
+### 2.0.2 / 2024.10.17
+
+- fix(cli): set napi object property properly (#26344)
+- fix(ext/node): add null check for kStreamBaseField (#26368)
+- fix(install): don't attempt to cache specifiers that point to directories
+  (#26369)
+- fix(jupyter): fix panics for overslow subtraction (#26371)
+- fix(jupyter): update to the new logo (#26353)
+- fix(net): don't try to set nodelay on upgrade streams (#26342)
+- fix(node/fs): copyFile with `COPYFILE_EXCL` should not throw if the
+  destination doesn't exist (#26360)
+- fix(node/http): normalize header names in `ServerResponse` (#26339)
+- fix(runtime): send ws ping frames from inspector server (#26352)
+- fix: don't warn on ignored signals on windows (#26332)
+
+### 2.0.1 / 2024.10.16
+
+- feat(lsp): "deno/didRefreshDenoConfigurationTree" notifications (#26215)
+- feat(unstable): `--unstable-detect-cjs` for respecting explicit
+  `"type": "commonjs"` (#26149)
+- fix(add): create deno.json when running `deno add jsr:<pkg>` (#26275)
+- fix(add): exact version should not have range `^` specifier (#26302)
+- fix(child_process): map node `--no-warnings` flag to `--quiet` (#26288)
+- fix(cli): add prefix to install commands in help (#26318)
+- fix(cli): consolidate pkg parser for install & remove (#26298)
+- fix(cli): named export takes precedence over default export in doc testing
+  (#26112)
+- fix(cli): improve deno info output for npm packages (#25906)
+- fix(console/ext/repl): support using parseFloat() (#25900)
+- fix(ext/console): apply coloring for console.table (#26280)
+- fix(ext/napi): pass user context to napi_threadsafe_fn finalizers (#26229)
+- fix(ext/node): allow writing to tty columns (#26201)
+- fix(ext/node): compute pem length (upper bound) for key exports (#26231)
+- fix(ext/node): fix dns.lookup result ordering (#26264)
+- fix(ext/node): handle http2 server ending stream (#26235)
+- fix(ext/node): implement TCP.setNoDelay (#26263)
+- fix(ext/node): timingSafeEqual account for AB byteOffset (#26292)
+- fix(ext/node): use primordials in `ext/node/polyfills/internal/buffer.mjs`
+  (#24993)
+- fix(ext/webgpu): allow GL backend on Windows (#26206)
+- fix(install): duplicate dependencies in `package.json` (#26128)
+- fix(install): handle pkg with dep on self when pkg part of peer dep resolution
+  (#26277)
+- fix(install): retry downloads of registry info / tarballs (#26278)
+- fix(install): support installing npm package with alias (#26246)
+- fix(jupyter): copy kernels icons to the kernel directory (#26084)
+- fix(jupyter): keep running event loop when waiting for messages (#26049)
+- fix(lsp): relative completions for bare import-mapped specifiers (#26137)
+- fix(node): make `process.stdout.isTTY` writable (#26130)
+- fix(node/util): export `styleText` from `node:util` (#26194)
+- fix(npm): support `--allow-scripts` on `deno run` (and `deno add`,
+  `deno test`, etc) (#26075)
+- fix(repl): importing json files (#26053)
+- fix(repl): remove check flags (#26140)
+- fix(unstable/worker): ensure import permissions are passed (#26101)
+- fix: add hint for missing `document` global in terminal error (#26218)
+- fix: do not panic on wsl share file paths on windows (#26081)
+- fix: do not panic running remote cjs module (#26259)
+- fix: do not panic when using methods on classes and interfaces in deno doc
+  html output (#26100)
+- fix: improve suggestions and hints when using CommonJS modules (#26287)
+- fix: node-api function call should use preamble (#26297)
+- fix: panic in `prepare_stack_trace_callback` when global interceptor throws
+  (#26241)
+- fix: use syntect for deno doc html generation (#26322)
+- perf(http): avoid clone getting request method and url (#26250)
+- perf(http): cache webidl.converters lookups in ext/fetch/23_response.js
+  (#26256)
+- perf(http): make heap allocation for path conditional (#26289)
+- perf: use fast calls for microtask ops (#26236)
+
 ### 2.0.0 / 2024.10.09
 
 Read announcement blog post at: https://deno.com/blog/v2
diff --git a/bench_util/Cargo.toml b/bench_util/Cargo.toml
index 4b886a2907..31c27b9a9d 100644
--- a/bench_util/Cargo.toml
+++ b/bench_util/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_bench_util"
-version = "0.165.0"
+version = "0.169.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/cli/Cargo.toml b/cli/Cargo.toml
index 8d1d1d1241..a3e2b71f00 100644
--- a/cli/Cargo.toml
+++ b/cli/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno"
-version = "2.0.0"
+version = "2.0.4"
 authors.workspace = true
 default-run = "deno"
 edition.workspace = true
@@ -38,6 +38,11 @@ path = "./bench/lsp_bench_standalone.rs"
 
 [features]
 default = ["upgrade", "__vendored_zlib_ng"]
+# A feature that enables heap profiling with dhat on Linux.
+# 1. Compile with `cargo build --profile=release-with-debug --features=dhat-heap`
+# 2. Run the executable. It will output a dhat-heap.json file.
+# 3. Open the json file in https://nnethercote.github.io/dh_view/dh_view.html
+dhat-heap = ["dhat"]
 # A feature that enables the upgrade subcommand and the background check for
 # available updates (of deno binary). This is typically disabled for (Linux)
 # distribution packages.
@@ -65,11 +70,11 @@ winres.workspace = true
 [dependencies]
 deno_ast = { workspace = true, features = ["bundler", "cjs", "codegen", "proposal", "react", "sourcemap", "transforms", "typescript", "view", "visit"] }
 deno_cache_dir = { workspace = true }
-deno_config = { version = "=0.37.1", features = ["workspace", "sync"] }
+deno_config = { version = "=0.37.2", features = ["workspace", "sync"] }
 deno_core = { workspace = true, features = ["include_js_files_for_snapshotting"] }
-deno_doc = { version = "0.153.0", features = ["html"] }
-deno_graph = { version = "=0.83.3" }
-deno_lint = { version = "=0.67.0", features = ["docs"] }
+deno_doc = { version = "0.156.0", default-features = false, features = ["rust", "html", "syntect"] }
+deno_graph = { version = "=0.84.1" }
+deno_lint = { version = "=0.68.0", features = ["docs"] }
 deno_lockfile.workspace = true
 deno_npm.workspace = true
 deno_package_json.workspace = true
@@ -79,9 +84,7 @@ deno_runtime = { workspace = true, features = ["include_js_files_for_snapshottin
 deno_semver.workspace = true
 deno_task_shell = "=0.18.1"
 deno_terminal.workspace = true
-eszip = "=0.79.1"
 libsui = "0.4.0"
-napi_sym.workspace = true
 node_resolver.workspace = true
 
 anstream = "0.6.14"
@@ -94,16 +97,17 @@ chrono = { workspace = true, features = ["now"] }
 clap = { version = "=4.5.16", features = ["env", "string", "wrap_help", "error-context"] }
 clap_complete = "=4.5.24"
 clap_complete_fig = "=4.5.2"
-color-print = "0.3.5"
+color-print.workspace = true
 console_static_text.workspace = true
 dashmap.workspace = true
 data-encoding.workspace = true
+dhat = { version = "0.3.3", optional = true }
 dissimilar = "=1.0.4"
 dotenvy = "0.15.7"
-dprint-plugin-json = "=0.19.3"
-dprint-plugin-jupyter = "=0.1.3"
+dprint-plugin-json = "=0.19.4"
+dprint-plugin-jupyter = "=0.1.5"
 dprint-plugin-markdown = "=0.17.8"
-dprint-plugin-typescript = "=0.93.0"
+dprint-plugin-typescript = "=0.93.1"
 env_logger = "=0.10.0"
 fancy-regex = "=0.10.0"
 faster-hex.workspace = true
@@ -117,15 +121,15 @@ http-body-util.workspace = true
 hyper-util.workspace = true
 import_map = { version = "=0.20.1", features = ["ext"] }
 indexmap.workspace = true
-jsonc-parser.workspace = true
+jsonc-parser = { workspace = true, features = ["cst", "serde"] }
 jupyter_runtime = { package = "runtimelib", version = "=0.14.0" }
 lazy-regex.workspace = true
 libc.workspace = true
 libz-sys.workspace = true
 log = { workspace = true, features = ["serde"] }
 lsp-types.workspace = true
-malva = "=0.10.1"
-markup_fmt = "=0.13.1"
+malva = "=0.11.0"
+markup_fmt = "=0.15.0"
 memmem.workspace = true
 monch.workspace = true
 notify.workspace = true
@@ -162,7 +166,6 @@ typed-arena = "=2.0.2"
 uuid = { workspace = true, features = ["serde"] }
 walkdir = "=2.3.2"
 which.workspace = true
-yoke.workspace = true
 zeromq.workspace = true
 zip = { version = "2.1.6", default-features = false, features = ["deflate-flate2"] }
 zstd.workspace = true
@@ -170,14 +173,12 @@ zstd.workspace = true
 [target.'cfg(windows)'.dependencies]
 junction.workspace = true
 winapi = { workspace = true, features = ["knownfolders", "mswsock", "objbase", "shlobj", "tlhelp32", "winbase", "winerror", "winsock2"] }
-windows-sys.workspace = true
 
 [target.'cfg(unix)'.dependencies]
 nix.workspace = true
 
 [dev-dependencies]
 deno_bench_util.workspace = true
-libuv-sys-lite = "=1.48.2"
 pretty_assertions.workspace = true
 test_util.workspace = true
 
diff --git a/cli/args/flags.rs b/cli/args/flags.rs
index 258712ca92..1a1213aac2 100644
--- a/cli/args/flags.rs
+++ b/cli/args/flags.rs
@@ -575,7 +575,8 @@ fn parse_packages_allowed_scripts(s: &str) -> Result<String, AnyError> {
 pub struct UnstableConfig {
   // TODO(bartlomieju): remove in Deno 2.5
   pub legacy_flag_enabled: bool, // --unstable
-  pub bare_node_builtins: bool,  // --unstable-bare-node-builts
+  pub bare_node_builtins: bool,
+  pub detect_cjs: bool,
   pub sloppy_imports: bool,
   pub features: Vec<String>, // --unstabe-kv --unstable-cron
 }
@@ -1177,9 +1178,9 @@ static DENO_HELP: &str = cstr!(
 
   <y>Dependency management:</>
     <g>add</>          Add dependencies
-                  <p(245)>deno add @std/assert  |  deno add npm:express</>
-    <g>install</>      Install script as an executable
-    <g>uninstall</>    Uninstall a script previously installed with deno install
+                  <p(245)>deno add jsr:@std/assert  |  deno add npm:express</>
+    <g>install</>      Installs dependencies either in the local project or globally to a bin directory
+    <g>uninstall</>    Uninstalls a dependency or an executable script in the installation root's bin directory
     <g>remove</>       Remove dependencies from the configuration file
 
   <y>Tooling:</>
@@ -1342,7 +1343,7 @@ pub fn flags_from_vec(args: Vec<OsString>) -> clap::error::Result<Flags> {
     }
 
     match subcommand.as_str() {
-      "add" => add_parse(&mut flags, &mut m),
+      "add" => add_parse(&mut flags, &mut m)?,
       "remove" => remove_parse(&mut flags, &mut m),
       "bench" => bench_parse(&mut flags, &mut m)?,
       "bundle" => bundle_parse(&mut flags, &mut m),
@@ -1528,7 +1529,7 @@ pub fn clap_root() -> Command {
   );
 
   run_args(Command::new("deno"), true)
-    .args(unstable_args(UnstableArgsConfig::ResolutionAndRuntime))
+    .with_unstable_args(UnstableArgsConfig::ResolutionAndRuntime)
     .next_line_help(false)
     .bin_name("deno")
     .styles(
@@ -1630,7 +1631,7 @@ fn command(
 ) -> Command {
   Command::new(name)
     .about(about)
-    .args(unstable_args(unstable_args_config))
+    .with_unstable_args(unstable_args_config)
 }
 
 fn help_subcommand(app: &Command) -> Command {
@@ -1658,10 +1659,10 @@ fn add_subcommand() -> Command {
     "add",
     cstr!(
       "Add dependencies to your configuration file.
-  <p(245)>deno add @std/path</>
+  <p(245)>deno add jsr:@std/path</>
 
 You can add multiple dependencies at once:
-  <p(245)>deno add @std/path @std/assert</>"
+  <p(245)>deno add jsr:@std/path jsr:@std/assert</>"
     ),
     UnstableArgsConfig::None,
   )
@@ -1675,6 +1676,7 @@ You can add multiple dependencies at once:
           .action(ArgAction::Append),
       )
       .arg(add_dev_arg())
+      .arg(allow_scripts_arg())
   })
 }
 
@@ -1717,7 +1719,7 @@ If you specify a directory instead of a file, the path is expanded to all contai
     UnstableArgsConfig::ResolutionAndRuntime,
   )
   .defer(|cmd| {
-    runtime_args(cmd, true, false)
+    runtime_args(cmd, true, false, true)
       .arg(check_arg(true))
       .arg(
         Arg::new("json")
@@ -1854,6 +1856,7 @@ Unless --reload is specified, this command will not re-download already cached d
             .required_unless_present("help")
             .value_hint(ValueHint::FilePath),
         )
+        .arg(frozen_lockfile_arg())
         .arg(allow_import_arg())
       }
     )
@@ -1881,7 +1884,7 @@ On the first invocation with deno will download the proper binary and cache it i
     UnstableArgsConfig::ResolutionAndRuntime,
   )
   .defer(|cmd| {
-    runtime_args(cmd, true, false)
+    runtime_args(cmd, true, false, true)
       .arg(check_arg(true))
       .arg(
         Arg::new("include")
@@ -2202,7 +2205,7 @@ This command has implicit access to all permissions.
     UnstableArgsConfig::ResolutionAndRuntime,
   )
   .defer(|cmd| {
-    runtime_args(cmd, false, true)
+    runtime_args(cmd, false, true, true)
       .arg(check_arg(false))
       .arg(executable_ext_arg())
       .arg(
@@ -2271,7 +2274,7 @@ Ignore formatting a file by adding an ignore comment at the top of the file:
             "sass", "less", "html", "svelte", "vue", "astro", "yml", "yaml",
             "ipynb",
           ])
-          .help_heading(FMT_HEADING),
+          .help_heading(FMT_HEADING).requires("files"),
       )
       .arg(
         Arg::new("ignore")
@@ -2468,7 +2471,7 @@ in the package cache. If no dependency is specified, installs all dependencies l
 If the <p(245)>--entrypoint</> flag is passed, installs the dependencies of the specified entrypoint(s).
 
   <p(245)>deno install</>
-  <p(245)>deno install @std/bytes</>
+  <p(245)>deno install jsr:@std/bytes</>
   <p(245)>deno install npm:chalk</>
   <p(245)>deno install --entrypoint entry1.ts entry2.ts</>
 
@@ -2501,7 +2504,7 @@ The installation root is determined, in order of precedence:
 These must be added to the path manually if required."), UnstableArgsConfig::ResolutionAndRuntime)
     .visible_alias("i")
     .defer(|cmd| {
-      permission_args(runtime_args(cmd, false, true), Some("global"))
+      permission_args(runtime_args(cmd, false, true, false), Some("global"))
         .arg(check_arg(true))
         .arg(allow_scripts_arg())
         .arg(
@@ -2767,8 +2770,13 @@ It is especially useful for quick prototyping and checking snippets of code.
 
 TypeScript is supported, however it is not type-checked, only transpiled."
   ), UnstableArgsConfig::ResolutionAndRuntime)
-    .defer(|cmd| runtime_args(cmd, true, true)
-      .arg(check_arg(false))
+    .defer(|cmd| {
+      let cmd = compile_args_without_check_args(cmd);
+      let cmd = inspect_args(cmd);
+      let cmd = permission_args(cmd, None);
+      let cmd = runtime_misc_args(cmd);
+
+      cmd
       .arg(
         Arg::new("eval-file")
           .long("eval-file")
@@ -2787,7 +2795,7 @@ TypeScript is supported, however it is not type-checked, only transpiled."
       .after_help(cstr!("<y>Environment variables:</>
   <g>DENO_REPL_HISTORY</>  Set REPL history file path. History file is disabled when the value is empty.
                        <p(245)>[default: $DENO_DIR/deno_history.txt]</>"))
-    )
+    })
     .arg(env_file_arg())
     .arg(
       Arg::new("args")
@@ -2799,7 +2807,7 @@ TypeScript is supported, however it is not type-checked, only transpiled."
 }
 
 fn run_args(command: Command, top_level: bool) -> Command {
-  runtime_args(command, true, true)
+  runtime_args(command, true, true, true)
     .arg(check_arg(false))
     .arg(watch_arg(true))
     .arg(hmr_arg(true))
@@ -2855,7 +2863,7 @@ Start a server defined in server.ts:
 Start a server defined in server.ts, watching for changes and running on port 5050:
   <p(245)>deno serve --watch --port 5050 server.ts</>
 
-<y>Read more:</> <c>https://docs.deno.com/go/serve</>"), UnstableArgsConfig::ResolutionAndRuntime), true, true)
+<y>Read more:</> <c>https://docs.deno.com/go/serve</>"), UnstableArgsConfig::ResolutionAndRuntime), true, true, true)
     .arg(
       Arg::new("port")
         .long("port")
@@ -2929,7 +2937,7 @@ or <c>**/__tests__/**</>:
           UnstableArgsConfig::ResolutionAndRuntime
     )
     .defer(|cmd|
-      runtime_args(cmd, true, true)
+      runtime_args(cmd, true, true, true)
       .arg(check_arg(true))
       .arg(
         Arg::new("ignore")
@@ -3642,6 +3650,7 @@ fn runtime_args(
   app: Command,
   include_perms: bool,
   include_inspector: bool,
+  include_allow_scripts: bool,
 ) -> Command {
   let app = compile_args(app);
   let app = if include_perms {
@@ -3654,6 +3663,15 @@ fn runtime_args(
   } else {
     app
   };
+  let app = if include_allow_scripts {
+    app.arg(allow_scripts_arg())
+  } else {
+    app
+  };
+  runtime_misc_args(app)
+}
+
+fn runtime_misc_args(app: Command) -> Command {
   app
     .arg(frozen_lockfile_arg())
     .arg(cached_only_arg())
@@ -4135,23 +4153,29 @@ enum UnstableArgsConfig {
   ResolutionAndRuntime,
 }
 
-struct UnstableArgsIter {
-  idx: usize,
-  cfg: UnstableArgsConfig,
+trait CommandExt {
+  fn with_unstable_args(self, cfg: UnstableArgsConfig) -> Self;
 }
 
-impl Iterator for UnstableArgsIter {
-  type Item = Arg;
+impl CommandExt for Command {
+  fn with_unstable_args(self, cfg: UnstableArgsConfig) -> Self {
+    let mut next_display_order = {
+      let mut value = 1000;
+      move || {
+        value += 1;
+        value
+      }
+    };
 
-  fn next(&mut self) -> Option<Self::Item> {
-    let arg = if self.idx == 0 {
+    let mut cmd = self.arg(
       Arg::new("unstable")
-        .long("unstable")
-        .help(cstr!("Enable all unstable features and APIs. Instead of using this flag, consider enabling individual unstable features
+      .long("unstable")
+      .help(cstr!("Enable all unstable features and APIs. Instead of using this flag, consider enabling individual unstable features
   <p(245)>To view the list of individual unstable feature flags, run this command again with --help=unstable</>"))
-        .action(ArgAction::SetTrue)
-        .hide(matches!(self.cfg, UnstableArgsConfig::None))
-    } else if self.idx == 1 {
+      .action(ArgAction::SetTrue)
+      .hide(matches!(cfg, UnstableArgsConfig::None))
+      .display_order(next_display_order())
+    ).arg(
       Arg::new("unstable-bare-node-builtins")
         .long("unstable-bare-node-builtins")
         .help("Enable unstable bare node builtins feature")
@@ -4159,20 +4183,36 @@ impl Iterator for UnstableArgsIter {
         .value_parser(FalseyValueParser::new())
         .action(ArgAction::SetTrue)
         .hide(true)
-        .long_help(match self.cfg {
+        .long_help(match cfg {
           UnstableArgsConfig::None => None,
           UnstableArgsConfig::ResolutionOnly
           | UnstableArgsConfig::ResolutionAndRuntime => Some("true"),
         })
         .help_heading(UNSTABLE_HEADING)
-    } else if self.idx == 2 {
+        .display_order(next_display_order()),
+    ).arg(
+      Arg::new("unstable-detect-cjs")
+        .long("unstable-detect-cjs")
+        .help("Reads the package.json type field in a project to treat .js files as .cjs")
+        .value_parser(FalseyValueParser::new())
+        .action(ArgAction::SetTrue)
+        .hide(true)
+        .long_help(match cfg {
+          UnstableArgsConfig::None => None,
+          UnstableArgsConfig::ResolutionOnly
+          | UnstableArgsConfig::ResolutionAndRuntime => Some("true"),
+        })
+        .help_heading(UNSTABLE_HEADING)
+        .display_order(next_display_order())
+    ).arg(
       Arg::new("unstable-byonm")
         .long("unstable-byonm")
         .value_parser(FalseyValueParser::new())
         .action(ArgAction::SetTrue)
         .hide(true)
         .help_heading(UNSTABLE_HEADING)
-    } else if self.idx == 3 {
+        .display_order(next_display_order()),
+    ).arg(
       Arg::new("unstable-sloppy-imports")
       .long("unstable-sloppy-imports")
       .help("Enable unstable resolving of specifiers by extension probing, .js to .ts, and directory probing")
@@ -4180,40 +4220,39 @@ impl Iterator for UnstableArgsIter {
       .value_parser(FalseyValueParser::new())
       .action(ArgAction::SetTrue)
       .hide(true)
-      .long_help(match self.cfg {
+      .long_help(match cfg {
         UnstableArgsConfig::None => None,
         UnstableArgsConfig::ResolutionOnly | UnstableArgsConfig::ResolutionAndRuntime => Some("true")
       })
       .help_heading(UNSTABLE_HEADING)
-    } else if self.idx > 3 {
-      let granular_flag = crate::UNSTABLE_GRANULAR_FLAGS.get(self.idx - 4)?;
-      Arg::new(format!("unstable-{}", granular_flag.name))
-        .long(format!("unstable-{}", granular_flag.name))
-        .help(granular_flag.help_text)
-        .action(ArgAction::SetTrue)
-        .hide(true)
-        .help_heading(UNSTABLE_HEADING)
-        // we don't render long help, so using it here as a sort of metadata
-        .long_help(if granular_flag.show_in_help {
-          match self.cfg {
-            UnstableArgsConfig::None | UnstableArgsConfig::ResolutionOnly => {
-              None
-            }
-            UnstableArgsConfig::ResolutionAndRuntime => Some("true"),
-          }
-        } else {
-          None
-        })
-    } else {
-      return None;
-    };
-    self.idx += 1;
-    Some(arg.display_order(self.idx + 1000))
-  }
-}
+      .display_order(next_display_order())
+    );
 
-fn unstable_args(cfg: UnstableArgsConfig) -> impl IntoIterator<Item = Arg> {
-  UnstableArgsIter { idx: 0, cfg }
+    for granular_flag in crate::UNSTABLE_GRANULAR_FLAGS.iter() {
+      cmd = cmd.arg(
+        Arg::new(format!("unstable-{}", granular_flag.name))
+          .long(format!("unstable-{}", granular_flag.name))
+          .help(granular_flag.help_text)
+          .action(ArgAction::SetTrue)
+          .hide(true)
+          .help_heading(UNSTABLE_HEADING)
+          // we don't render long help, so using it here as a sort of metadata
+          .long_help(if granular_flag.show_in_help {
+            match cfg {
+              UnstableArgsConfig::None | UnstableArgsConfig::ResolutionOnly => {
+                None
+              }
+              UnstableArgsConfig::ResolutionAndRuntime => Some("true"),
+            }
+          } else {
+            None
+          })
+          .display_order(next_display_order()),
+      );
+    }
+
+    cmd
+  }
 }
 
 fn allow_scripts_arg_parse(
@@ -4235,8 +4274,13 @@ fn allow_scripts_arg_parse(
   Ok(())
 }
 
-fn add_parse(flags: &mut Flags, matches: &mut ArgMatches) {
+fn add_parse(
+  flags: &mut Flags,
+  matches: &mut ArgMatches,
+) -> clap::error::Result<()> {
+  allow_scripts_arg_parse(flags, matches)?;
   flags.subcommand = DenoSubcommand::Add(add_parse_inner(matches, None));
+  Ok(())
 }
 
 fn add_parse_inner(
@@ -4262,7 +4306,7 @@ fn bench_parse(
 ) -> clap::error::Result<()> {
   flags.type_check_mode = TypeCheckMode::Local;
 
-  runtime_args_parse(flags, matches, true, false)?;
+  runtime_args_parse(flags, matches, true, false, true)?;
   ext_arg_parse(flags, matches);
 
   // NOTE: `deno bench` always uses `--no-prompt`, tests shouldn't ever do
@@ -4330,6 +4374,7 @@ fn check_parse(
   flags.type_check_mode = TypeCheckMode::Local;
   compile_args_without_check_parse(flags, matches)?;
   unstable_args_parse(flags, matches, UnstableArgsConfig::ResolutionAndRuntime);
+  frozen_lockfile_arg_parse(flags, matches);
   let files = matches.remove_many::<String>("file").unwrap().collect();
   if matches.get_flag("all") || matches.get_flag("remote") {
     flags.type_check_mode = TypeCheckMode::All;
@@ -4352,7 +4397,7 @@ fn compile_parse(
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
   flags.type_check_mode = TypeCheckMode::Local;
-  runtime_args_parse(flags, matches, true, false)?;
+  runtime_args_parse(flags, matches, true, false, true)?;
 
   let mut script = matches.remove_many::<String>("script_arg").unwrap();
   let source_file = script.next().unwrap();
@@ -4527,7 +4572,7 @@ fn eval_parse(
   flags: &mut Flags,
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
-  runtime_args_parse(flags, matches, false, true)?;
+  runtime_args_parse(flags, matches, false, true, false)?;
   unstable_args_parse(flags, matches, UnstableArgsConfig::ResolutionAndRuntime);
   flags.allow_all();
 
@@ -4620,7 +4665,7 @@ fn install_parse(
   flags: &mut Flags,
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
-  runtime_args_parse(flags, matches, true, true)?;
+  runtime_args_parse(flags, matches, true, true, false)?;
 
   let global = matches.get_flag("global");
   if global {
@@ -4846,8 +4891,18 @@ fn repl_parse(
   flags: &mut Flags,
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
-  runtime_args_parse(flags, matches, true, true)?;
-  unsafely_ignore_certificate_errors_parse(flags, matches);
+  unstable_args_parse(flags, matches, UnstableArgsConfig::ResolutionAndRuntime);
+  compile_args_without_check_parse(flags, matches)?;
+  cached_only_arg_parse(flags, matches);
+  frozen_lockfile_arg_parse(flags, matches);
+  permission_args_parse(flags, matches)?;
+  inspect_arg_parse(flags, matches);
+  location_arg_parse(flags, matches);
+  v8_flags_arg_parse(flags, matches);
+  seed_arg_parse(flags, matches);
+  enable_testing_features_arg_parse(flags, matches);
+  env_file_arg_parse(flags, matches);
+  strace_ops_parse(flags, matches);
 
   let eval_files = matches
     .remove_many::<String>("eval-file")
@@ -4879,7 +4934,7 @@ fn run_parse(
   mut app: Command,
   bare: bool,
 ) -> clap::error::Result<()> {
-  runtime_args_parse(flags, matches, true, true)?;
+  runtime_args_parse(flags, matches, true, true, true)?;
   ext_arg_parse(flags, matches);
 
   flags.code_cache_enabled = !matches.get_flag("no-code-cache");
@@ -4920,7 +4975,7 @@ fn serve_parse(
 
   let worker_count = parallel_arg_parse(matches).map(|v| v.get());
 
-  runtime_args_parse(flags, matches, true, true)?;
+  runtime_args_parse(flags, matches, true, true, true)?;
   // If the user didn't pass --allow-net, add this port to the network
   // allowlist. If the host is 0.0.0.0, we add :{port} and allow the same network perms
   // as if it was passed to --allow-net directly.
@@ -5015,7 +5070,7 @@ fn test_parse(
   matches: &mut ArgMatches,
 ) -> clap::error::Result<()> {
   flags.type_check_mode = TypeCheckMode::Local;
-  runtime_args_parse(flags, matches, true, true)?;
+  runtime_args_parse(flags, matches, true, true, true)?;
   ext_arg_parse(flags, matches);
 
   // NOTE: `deno test` always uses `--no-prompt`, tests shouldn't ever do
@@ -5380,6 +5435,7 @@ fn runtime_args_parse(
   matches: &mut ArgMatches,
   include_perms: bool,
   include_inspector: bool,
+  include_allow_scripts: bool,
 ) -> clap::error::Result<()> {
   unstable_args_parse(flags, matches, UnstableArgsConfig::ResolutionAndRuntime);
   compile_args_parse(flags, matches)?;
@@ -5391,6 +5447,9 @@ fn runtime_args_parse(
   if include_inspector {
     inspect_arg_parse(flags, matches);
   }
+  if include_allow_scripts {
+    allow_scripts_arg_parse(flags, matches)?;
+  }
   location_arg_parse(flags, matches);
   v8_flags_arg_parse(flags, matches);
   seed_arg_parse(flags, matches);
@@ -5662,6 +5721,7 @@ fn unstable_args_parse(
 
   flags.unstable_config.bare_node_builtins =
     matches.get_flag("unstable-bare-node-builtins");
+  flags.unstable_config.detect_cjs = matches.get_flag("unstable-detect-cjs");
   flags.unstable_config.sloppy_imports =
     matches.get_flag("unstable-sloppy-imports");
 
@@ -6742,6 +6802,32 @@ mod tests {
         ..Flags::default()
       }
     );
+
+    let r = flags_from_vec(svec!["deno", "fmt", "--ext", "html"]);
+    assert!(r.is_err());
+    let r = flags_from_vec(svec!["deno", "fmt", "--ext", "html", "./**"]);
+    assert_eq!(
+      r.unwrap(),
+      Flags {
+        subcommand: DenoSubcommand::Fmt(FmtFlags {
+          check: false,
+          files: FileFlags {
+            include: vec!["./**".to_string()],
+            ignore: vec![],
+          },
+          use_tabs: None,
+          line_width: None,
+          indent_width: None,
+          single_quote: None,
+          prose_wrap: None,
+          no_semicolons: None,
+          unstable_component: false,
+          watch: Default::default(),
+        }),
+        ext: Some("html".to_string()),
+        ..Flags::default()
+      }
+    );
   }
 
   #[test]
@@ -7390,7 +7476,7 @@ mod tests {
   #[test]
   fn repl_with_flags() {
     #[rustfmt::skip]
-    let r = flags_from_vec(svec!["deno", "repl", "-A", "--import-map", "import_map.json", "--no-remote", "--config", "tsconfig.json", "--no-check", "--reload", "--lock", "lock.json", "--cert", "example.crt", "--cached-only", "--location", "https:foo", "--v8-flags=--help", "--seed", "1", "--inspect=127.0.0.1:9229", "--unsafely-ignore-certificate-errors", "--env=.example.env"]);
+    let r = flags_from_vec(svec!["deno", "repl", "-A", "--import-map", "import_map.json", "--no-remote", "--config", "tsconfig.json", "--reload", "--lock", "lock.json", "--cert", "example.crt", "--cached-only", "--location", "https:foo", "--v8-flags=--help", "--seed", "1", "--inspect=127.0.0.1:9229", "--unsafely-ignore-certificate-errors", "--env=.example.env"]);
     assert_eq!(
       r.unwrap(),
       Flags {
@@ -7438,7 +7524,6 @@ mod tests {
           allow_write: Some(vec![]),
           ..Default::default()
         },
-        type_check_mode: TypeCheckMode::None,
         ..Flags::default()
       }
     );
@@ -7460,7 +7545,6 @@ mod tests {
           eval: None,
           is_default_command: false,
         }),
-        type_check_mode: TypeCheckMode::None,
         ..Flags::default()
       }
     );
@@ -8862,8 +8946,12 @@ mod tests {
 
   #[test]
   fn test_no_colon_in_value_name() {
-    let app =
-      runtime_args(Command::new("test_inspect_completion_value"), true, true);
+    let app = runtime_args(
+      Command::new("test_inspect_completion_value"),
+      true,
+      true,
+      false,
+    );
     let inspect_args = app
       .get_arguments()
       .filter(|arg| arg.get_id() == "inspect")
diff --git a/cli/args/mod.rs b/cli/args/mod.rs
index 07906a86ac..e19025f8b1 100644
--- a/cli/args/mod.rs
+++ b/cli/args/mod.rs
@@ -46,6 +46,7 @@ pub use flags::*;
 pub use lockfile::CliLockfile;
 pub use lockfile::CliLockfileReadFromPathOptions;
 pub use package_json::NpmInstallDepsProvider;
+pub use package_json::PackageJsonDepValueParseWithLocationError;
 
 use deno_ast::ModuleSpecifier;
 use deno_core::anyhow::bail;
@@ -200,6 +201,8 @@ pub fn ts_config_to_transpile_and_emit_options(
       precompile_jsx_dynamic_props: None,
       transform_jsx,
       var_decl_imports: false,
+      // todo(dsherret): support verbatim_module_syntax here properly
+      verbatim_module_syntax: false,
     },
     deno_ast::EmitOptions {
       inline_sources: options.inline_sources,
@@ -578,6 +581,7 @@ fn discover_npmrc(
     let resolved = npmrc
       .as_resolved(npm_registry_url())
       .context("Failed to resolve .npmrc options")?;
+    log::debug!(".npmrc found at: '{}'", path.display());
     Ok(Arc::new(resolved))
   }
 
@@ -963,6 +967,9 @@ impl CliOptions {
     match self.sub_command() {
       DenoSubcommand::Cache(_) => GraphKind::All,
       DenoSubcommand::Check(_) => GraphKind::TypesOnly,
+      DenoSubcommand::Install(InstallFlags {
+        kind: InstallKind::Local(_),
+      }) => GraphKind::All,
       _ => self.type_check_mode().as_graph_kind(),
     }
   }
@@ -1448,6 +1455,12 @@ impl CliOptions {
       watch: Some(WatchFlagsWithPaths { hmr, .. }),
       ..
     }) = &self.flags.subcommand
+    {
+      *hmr
+    } else if let DenoSubcommand::Serve(ServeFlags {
+      watch: Some(WatchFlagsWithPaths { hmr, .. }),
+      ..
+    }) = &self.flags.subcommand
     {
       *hmr
     } else {
@@ -1576,6 +1589,11 @@ impl CliOptions {
       || self.workspace().has_unstable("bare-node-builtins")
   }
 
+  pub fn unstable_detect_cjs(&self) -> bool {
+    self.flags.unstable_config.detect_cjs
+      || self.workspace().has_unstable("detect-cjs")
+  }
+
   fn byonm_enabled(&self) -> bool {
     // check if enabled via unstable
     self.node_modules_dir().ok().flatten() == Some(NodeModulesDirMode::Manual)
@@ -1586,6 +1604,15 @@ impl CliOptions {
   }
 
   pub fn use_byonm(&self) -> bool {
+    if matches!(
+      self.sub_command(),
+      DenoSubcommand::Install(_)
+        | DenoSubcommand::Add(_)
+        | DenoSubcommand::Remove(_)
+    ) {
+      // For `deno install/add/remove` we want to force the managed resolver so it can set up `node_modules/` directory.
+      return false;
+    }
     if self.node_modules_dir().ok().flatten().is_none()
       && self.maybe_node_modules_folder.is_some()
       && self
@@ -1620,21 +1647,17 @@ impl CliOptions {
       });
 
     if !from_config_file.is_empty() {
-      // collect unstable granular flags
-      let mut all_valid_unstable_flags: Vec<&str> =
-        crate::UNSTABLE_GRANULAR_FLAGS
-          .iter()
-          .map(|granular_flag| granular_flag.name)
-          .collect();
-
-      let mut another_unstable_flags = Vec::from([
-        "sloppy-imports",
-        "byonm",
-        "bare-node-builtins",
-        "fmt-component",
-      ]);
-      // add more unstable flags to the same vector holding granular flags
-      all_valid_unstable_flags.append(&mut another_unstable_flags);
+      let all_valid_unstable_flags: Vec<&str> = crate::UNSTABLE_GRANULAR_FLAGS
+        .iter()
+        .map(|granular_flag| granular_flag.name)
+        .chain([
+          "sloppy-imports",
+          "byonm",
+          "bare-node-builtins",
+          "fmt-component",
+          "detect-cjs",
+        ])
+        .collect();
 
       // check and warn if the unstable flag of config file isn't supported, by
       // iterating through the vector holding the unstable flags
@@ -1667,6 +1690,10 @@ impl CliOptions {
     if let DenoSubcommand::Run(RunFlags {
       watch: Some(WatchFlagsWithPaths { paths, .. }),
       ..
+    })
+    | DenoSubcommand::Serve(ServeFlags {
+      watch: Some(WatchFlagsWithPaths { paths, .. }),
+      ..
     }) = &self.flags.subcommand
     {
       full_paths.extend(paths.iter().map(|path| self.initial_cwd.join(path)));
diff --git a/cli/args/package_json.rs b/cli/args/package_json.rs
index 2ef39a30d2..7dc75550c3 100644
--- a/cli/args/package_json.rs
+++ b/cli/args/package_json.rs
@@ -5,10 +5,12 @@ use std::sync::Arc;
 
 use deno_config::workspace::Workspace;
 use deno_core::serde_json;
+use deno_core::url::Url;
 use deno_package_json::PackageJsonDepValue;
 use deno_package_json::PackageJsonDepValueParseError;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_semver::package::PackageReq;
+use thiserror::Error;
 
 #[derive(Debug)]
 pub struct InstallNpmRemotePkg {
@@ -23,11 +25,20 @@ pub struct InstallNpmWorkspacePkg {
   pub target_dir: PathBuf,
 }
 
+#[derive(Debug, Error, Clone)]
+#[error("Failed to install '{}'\n    at {}", alias, location)]
+pub struct PackageJsonDepValueParseWithLocationError {
+  pub location: Url,
+  pub alias: String,
+  #[source]
+  pub source: PackageJsonDepValueParseError,
+}
+
 #[derive(Debug, Default)]
 pub struct NpmInstallDepsProvider {
   remote_pkgs: Vec<InstallNpmRemotePkg>,
   workspace_pkgs: Vec<InstallNpmWorkspacePkg>,
-  pkg_json_dep_errors: Vec<PackageJsonDepValueParseError>,
+  pkg_json_dep_errors: Vec<PackageJsonDepValueParseWithLocationError>,
 }
 
 impl NpmInstallDepsProvider {
@@ -89,7 +100,13 @@ impl NpmInstallDepsProvider {
           let dep = match dep {
             Ok(dep) => dep,
             Err(err) => {
-              pkg_json_dep_errors.push(err);
+              pkg_json_dep_errors.push(
+                PackageJsonDepValueParseWithLocationError {
+                  location: pkg_json.specifier(),
+                  alias,
+                  source: err,
+                },
+              );
               continue;
             }
           };
@@ -150,7 +167,9 @@ impl NpmInstallDepsProvider {
     &self.workspace_pkgs
   }
 
-  pub fn pkg_json_dep_errors(&self) -> &[PackageJsonDepValueParseError] {
+  pub fn pkg_json_dep_errors(
+    &self,
+  ) -> &[PackageJsonDepValueParseWithLocationError] {
     &self.pkg_json_dep_errors
   }
 }
diff --git a/cli/bench/http.rs b/cli/bench/http.rs
deleted file mode 100644
index f739b76ba8..0000000000
--- a/cli/bench/http.rs
+++ /dev/null
@@ -1,167 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-use std::collections::HashMap;
-use std::net::TcpStream;
-use std::path::Path;
-use std::process::Command;
-use std::sync::atomic::AtomicU16;
-use std::sync::atomic::Ordering;
-use std::time::Duration;
-use std::time::Instant;
-
-use super::Result;
-
-pub use test_util::parse_wrk_output;
-pub use test_util::WrkOutput as HttpBenchmarkResult;
-// Some of the benchmarks in this file have been renamed. In case the history
-// somehow gets messed up:
-//   "node_http" was once called "node"
-//   "deno_tcp" was once called "deno"
-//   "deno_http" was once called "deno_net_http"
-
-const DURATION: &str = "10s";
-
-pub fn benchmark(
-  target_path: &Path,
-) -> Result<HashMap<String, HttpBenchmarkResult>> {
-  let deno_exe = test_util::deno_exe_path();
-  let deno_exe = deno_exe.to_string();
-
-  let hyper_hello_exe = target_path.join("test_server");
-  let hyper_hello_exe = hyper_hello_exe.to_str().unwrap();
-
-  let mut res = HashMap::new();
-  let manifest_dir = Path::new(env!("CARGO_MANIFEST_DIR"));
-  let http_dir = manifest_dir.join("bench").join("http");
-  for entry in std::fs::read_dir(&http_dir)? {
-    let entry = entry?;
-    let pathbuf = entry.path();
-    let path = pathbuf.to_str().unwrap();
-    if path.ends_with(".lua") {
-      continue;
-    }
-    let file_stem = pathbuf.file_stem().unwrap().to_str().unwrap();
-
-    let lua_script = http_dir.join(format!("{file_stem}.lua"));
-    let mut maybe_lua = None;
-    if lua_script.exists() {
-      maybe_lua = Some(lua_script.to_str().unwrap());
-    }
-
-    let port = get_port();
-    // deno run -A --unstable-net <path> <addr>
-    res.insert(
-      file_stem.to_string(),
-      run(
-        &[
-          deno_exe.as_str(),
-          "run",
-          "--allow-all",
-          "--unstable-net",
-          "--enable-testing-features-do-not-use",
-          path,
-          &server_addr(port),
-        ],
-        port,
-        None,
-        None,
-        maybe_lua,
-      )?,
-    );
-  }
-
-  res.insert("hyper".to_string(), hyper_http(hyper_hello_exe)?);
-
-  Ok(res)
-}
-
-fn run(
-  server_cmd: &[&str],
-  port: u16,
-  env: Option<Vec<(String, String)>>,
-  origin_cmd: Option<&[&str]>,
-  lua_script: Option<&str>,
-) -> Result<HttpBenchmarkResult> {
-  // Wait for port 4544 to become available.
-  // TODO Need to use SO_REUSEPORT with tokio::net::TcpListener.
-  std::thread::sleep(Duration::from_secs(5));
-
-  let mut origin = None;
-  if let Some(cmd) = origin_cmd {
-    let mut com = Command::new(cmd[0]);
-    com.args(&cmd[1..]);
-    if let Some(env) = env.clone() {
-      com.envs(env);
-    }
-    origin = Some(com.spawn()?);
-  };
-
-  println!("{}", server_cmd.join(" "));
-  let mut server = {
-    let mut com = Command::new(server_cmd[0]);
-    com.args(&server_cmd[1..]);
-    if let Some(env) = env {
-      com.envs(env);
-    }
-    com.spawn()?
-  };
-
-  // Wait for server to wake up.
-  let now = Instant::now();
-  let addr = format!("127.0.0.1:{port}");
-  while now.elapsed().as_secs() < 30 {
-    if TcpStream::connect(&addr).is_ok() {
-      break;
-    }
-    std::thread::sleep(Duration::from_millis(10));
-  }
-  TcpStream::connect(&addr).expect("Failed to connect to server in time");
-  println!("Server took {} ms to start", now.elapsed().as_millis());
-
-  let wrk = test_util::prebuilt_tool_path("wrk");
-  assert!(wrk.is_file());
-
-  let addr = format!("http://{addr}/");
-  let wrk = wrk.to_string();
-  let mut wrk_cmd = vec![wrk.as_str(), "-d", DURATION, "--latency", &addr];
-
-  if let Some(lua_script) = lua_script {
-    wrk_cmd.push("-s");
-    wrk_cmd.push(lua_script);
-  }
-
-  println!("{}", wrk_cmd.join(" "));
-  let output = test_util::run_collect(&wrk_cmd, None, None, None, true).0;
-
-  std::thread::sleep(Duration::from_secs(1)); // wait to capture failure. TODO racy.
-
-  println!("{output}");
-  assert!(
-    server.try_wait()?.map(|s| s.success()).unwrap_or(true),
-    "server ended with error"
-  );
-
-  server.kill()?;
-  if let Some(mut origin) = origin {
-    origin.kill()?;
-  }
-
-  Ok(parse_wrk_output(&output))
-}
-
-static NEXT_PORT: AtomicU16 = AtomicU16::new(4544);
-pub(crate) fn get_port() -> u16 {
-  let p = NEXT_PORT.load(Ordering::SeqCst);
-  NEXT_PORT.store(p.wrapping_add(1), Ordering::SeqCst);
-  p
-}
-
-fn server_addr(port: u16) -> String {
-  format!("0.0.0.0:{port}")
-}
-
-fn hyper_http(exe: &str) -> Result<HttpBenchmarkResult> {
-  let port = get_port();
-  println!("http_benchmark testing RUST hyper");
-  run(&[exe, &port.to_string()], port, None, None, None)
-}
diff --git a/cli/bench/http/deno_flash_hono_router.js b/cli/bench/http/deno_flash_hono_router.js
deleted file mode 100644
index baced0cece..0000000000
--- a/cli/bench/http/deno_flash_hono_router.js
+++ /dev/null
@@ -1,10 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-import { Hono } from "https://deno.land/x/hono@v2.0.9/mod.ts";
-
-const addr = Deno.args[0] || "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-
-const app = new Hono();
-app.get("/", (c) => c.text("Hello, World!"));
-
-Deno.serve({ port: Number(port), hostname }, app.fetch);
diff --git a/cli/bench/http/deno_flash_send_file.js b/cli/bench/http/deno_flash_send_file.js
deleted file mode 100644
index bf8541f8b0..0000000000
--- a/cli/bench/http/deno_flash_send_file.js
+++ /dev/null
@@ -1,14 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-const addr = Deno.args[0] || "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-const { serve } = Deno;
-
-const path = new URL("../testdata/128k.bin", import.meta.url).pathname;
-
-function handler() {
-  const file = Deno.openSync(path);
-  return new Response(file.readable);
-}
-
-serve({ hostname, port: Number(port) }, handler);
diff --git a/cli/bench/http/deno_http_read_headers.lua b/cli/bench/http/deno_http_read_headers.lua
deleted file mode 100644
index 64f1923ff3..0000000000
--- a/cli/bench/http/deno_http_read_headers.lua
+++ /dev/null
@@ -1,5 +0,0 @@
-wrk.headers["foo"] = "bar"
-wrk.headers["User-Agent"] = "Mozilla/5.0 (Macintosh; Intel Mac OS X 10_15_7) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/103.0.0.0 Safari/537.36"
-wrk.headers["Viewport-Width"] = "1920"
-wrk.headers["Accept"] = "text/html,application/xhtml+xml,application/xml;q=0.9,image/avif,image/webp,image/apng,*/*;q=0.8,application/signed-exchange;v=b3;q=0.9"
-wrk.headers["Accept-Language"] = "en,la;q=0.9"
\ No newline at end of file
diff --git a/cli/bench/http/deno_http_serve.js b/cli/bench/http/deno_http_serve.js
deleted file mode 100644
index 639982ce60..0000000000
--- a/cli/bench/http/deno_http_serve.js
+++ /dev/null
@@ -1,11 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-const addr = Deno.args[0] ?? "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-const { serve } = Deno;
-
-function handler() {
-  return new Response("Hello World");
-}
-
-serve({ hostname, port: Number(port), reusePort: true }, handler);
diff --git a/cli/bench/http/deno_post_bin.lua b/cli/bench/http/deno_post_bin.lua
deleted file mode 100644
index c8f5d3e3f7..0000000000
--- a/cli/bench/http/deno_post_bin.lua
+++ /dev/null
@@ -1,5 +0,0 @@
-wrk.method = "POST"
-wrk.headers["Content-Type"] = "application/octet-stream"
-
-file = io.open("./cli/bench/testdata/128k.bin", "rb")
-wrk.body = file:read("*a")
\ No newline at end of file
diff --git a/cli/bench/http/deno_post_json.lua b/cli/bench/http/deno_post_json.lua
deleted file mode 100644
index cc6c4e226d..0000000000
--- a/cli/bench/http/deno_post_json.lua
+++ /dev/null
@@ -1,3 +0,0 @@
-wrk.method = "POST"
-wrk.headers["Content-Type"] = "application/json"
-wrk.body = '{"hello":"deno"}'
\ No newline at end of file
diff --git a/cli/bench/http/deno_reactdom_ssr_flash.jsx b/cli/bench/http/deno_reactdom_ssr_flash.jsx
deleted file mode 100644
index eaabf89121..0000000000
--- a/cli/bench/http/deno_reactdom_ssr_flash.jsx
+++ /dev/null
@@ -1,25 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-import { renderToReadableStream } from "https://esm.run/react-dom/server";
-import * as React from "https://esm.run/react";
-const { serve } = Deno;
-const addr = Deno.args[0] || "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-
-const App = () => (
-  <html>
-    <body>
-      <h1>Hello World</h1>
-    </body>
-  </html>
-);
-
-const headers = {
-  headers: {
-    "Content-Type": "text/html",
-  },
-};
-
-serve({ hostname, port: Number(port) }, async () => {
-  return new Response(await renderToReadableStream(<App />), headers);
-});
diff --git a/cli/bench/http/deno_tcp.ts b/cli/bench/http/deno_tcp.ts
deleted file mode 100644
index b795910737..0000000000
--- a/cli/bench/http/deno_tcp.ts
+++ /dev/null
@@ -1,34 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-// Used for benchmarking Deno's networking.
-// TODO(bartlomieju): Replace this with a real HTTP server once
-// https://github.com/denoland/deno/issues/726 is completed.
-// Note: this is a keep-alive server.
-// deno-lint-ignore-file no-console
-const addr = Deno.args[0] || "127.0.0.1:4500";
-const [hostname, port] = addr.split(":");
-const listener = Deno.listen({ hostname, port: Number(port) });
-const response = new TextEncoder().encode(
-  "HTTP/1.1 200 OK\r\nContent-Length: 12\r\n\r\nHello World\n",
-);
-async function handle(conn: Deno.Conn): Promise<void> {
-  const buffer = new Uint8Array(1024);
-  try {
-    while (true) {
-      await conn.read(buffer);
-      await conn.write(response);
-    }
-  } catch (e) {
-    if (
-      !(e instanceof Deno.errors.BrokenPipe) &&
-      !(e instanceof Deno.errors.ConnectionReset)
-    ) {
-      throw e;
-    }
-  }
-  conn.close();
-}
-
-console.log("Listening on", addr);
-for await (const conn of listener) {
-  handle(conn);
-}
diff --git a/cli/bench/lsp.rs b/cli/bench/lsp.rs
index b088865c6b..7baaffca7e 100644
--- a/cli/bench/lsp.rs
+++ b/cli/bench/lsp.rs
@@ -150,7 +150,11 @@ fn bench_big_file_edits(deno_exe: &Path) -> Duration {
     .deno_exe(deno_exe)
     .build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": { "enable": true } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   client.write_notification(
     "textDocument/didOpen",
@@ -206,6 +210,8 @@ fn bench_code_lens(deno_exe: &Path) -> Duration {
     .deno_exe(deno_exe)
     .build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": {
     "enable": true,
     "codeLens": {
@@ -214,6 +220,8 @@ fn bench_code_lens(deno_exe: &Path) -> Duration {
       "test": true,
     },
   } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   client.write_notification(
     "textDocument/didOpen",
@@ -257,7 +265,11 @@ fn bench_find_replace(deno_exe: &Path) -> Duration {
     .deno_exe(deno_exe)
     .build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": { "enable": true } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   for i in 0..10 {
     client.write_notification(
@@ -341,7 +353,11 @@ fn bench_startup_shutdown(deno_exe: &Path) -> Duration {
     .deno_exe(deno_exe)
     .build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": { "enable": true } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   client.write_notification(
     "textDocument/didOpen",
diff --git a/cli/bench/lsp_bench_standalone.rs b/cli/bench/lsp_bench_standalone.rs
index 9c4f264ec9..3c946cfbe3 100644
--- a/cli/bench/lsp_bench_standalone.rs
+++ b/cli/bench/lsp_bench_standalone.rs
@@ -13,7 +13,11 @@ use test_util::lsp::LspClientBuilder;
 fn incremental_change_wait(bench: &mut Bencher) {
   let mut client = LspClientBuilder::new().use_diagnostic_sync(false).build();
   client.initialize_default();
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
   client.change_configuration(json!({ "deno": { "enable": true } }));
+  let (method, _): (String, Option<Value>) = client.read_notification();
+  assert_eq!(method, "deno/didRefreshDenoConfigurationTree");
 
   client.write_notification(
     "textDocument/didOpen",
diff --git a/cli/bench/main.rs b/cli/bench/main.rs
index 72fa7e9636..c3c42d2488 100644
--- a/cli/bench/main.rs
+++ b/cli/bench/main.rs
@@ -17,7 +17,6 @@ use std::process::Stdio;
 use std::time::SystemTime;
 use test_util::PathRef;
 
-mod http;
 mod lsp;
 
 fn read_json(filename: &Path) -> Result<Value> {
@@ -345,9 +344,11 @@ struct BenchResult {
   binary_size: HashMap<String, i64>,
   bundle_size: HashMap<String, i64>,
   cargo_deps: usize,
+  // TODO(bartlomieju): remove
   max_latency: HashMap<String, f64>,
   max_memory: HashMap<String, i64>,
   lsp_exec_time: HashMap<String, i64>,
+  // TODO(bartlomieju): remove
   req_per_sec: HashMap<String, i64>,
   syscall_count: HashMap<String, i64>,
   thread_count: HashMap<String, i64>,
@@ -362,7 +363,6 @@ async fn main() -> Result<()> {
     "binary_size",
     "cargo_deps",
     "lsp",
-    "http",
     "strace",
     "mem_usage",
   ];
@@ -427,21 +427,6 @@ async fn main() -> Result<()> {
     new_data.lsp_exec_time = lsp_exec_times;
   }
 
-  if benchmarks.contains(&"http") && cfg!(not(target_os = "windows")) {
-    let stats = http::benchmark(target_dir.as_path())?;
-    let req_per_sec = stats
-      .iter()
-      .map(|(name, result)| (name.clone(), result.requests as i64))
-      .collect();
-    new_data.req_per_sec = req_per_sec;
-    let max_latency = stats
-      .iter()
-      .map(|(name, result)| (name.clone(), result.latency))
-      .collect();
-
-    new_data.max_latency = max_latency;
-  }
-
   if cfg!(target_os = "linux") && benchmarks.contains(&"strace") {
     use std::io::Read;
 
diff --git a/cli/build.rs b/cli/build.rs
index aa5d3d18c6..2678a8dbb0 100644
--- a/cli/build.rs
+++ b/cli/build.rs
@@ -365,6 +365,9 @@ fn main() {
     return;
   }
 
+  deno_napi::print_linker_flags("deno");
+  deno_napi::print_linker_flags("denort");
+
   // Host snapshots won't work when cross compiling.
   let target = env::var("TARGET").unwrap();
   let host = env::var("HOST").unwrap();
@@ -374,58 +377,6 @@ fn main() {
     panic!("Cross compiling with snapshot is not supported.");
   }
 
-  let symbols_file_name = match env::consts::OS {
-    "android" | "freebsd" | "openbsd" => {
-      "generated_symbol_exports_list_linux.def".to_string()
-    }
-    os => format!("generated_symbol_exports_list_{}.def", os),
-  };
-  let symbols_path = std::path::Path::new("napi")
-    .join(symbols_file_name)
-    .canonicalize()
-    .expect(
-        "Missing symbols list! Generate using tools/napi/generate_symbols_lists.js",
-    );
-
-  println!("cargo:rustc-rerun-if-changed={}", symbols_path.display());
-
-  #[cfg(target_os = "windows")]
-  println!(
-    "cargo:rustc-link-arg-bin=deno=/DEF:{}",
-    symbols_path.display()
-  );
-
-  #[cfg(target_os = "macos")]
-  println!(
-    "cargo:rustc-link-arg-bin=deno=-Wl,-exported_symbols_list,{}",
-    symbols_path.display()
-  );
-
-  #[cfg(target_os = "linux")]
-  {
-    // If a custom compiler is set, the glibc version is not reliable.
-    // Here, we assume that if a custom compiler is used, that it will be modern enough to support a dynamic symbol list.
-    if env::var("CC").is_err()
-      && glibc_version::get_version()
-        .map(|ver| ver.major <= 2 && ver.minor < 35)
-        .unwrap_or(false)
-    {
-      println!("cargo:warning=Compiling with all symbols exported, this will result in a larger binary. Please use glibc 2.35 or later for an optimised build.");
-      println!("cargo:rustc-link-arg-bin=deno=-rdynamic");
-    } else {
-      println!(
-        "cargo:rustc-link-arg-bin=deno=-Wl,--export-dynamic-symbol-list={}",
-        symbols_path.display()
-      );
-    }
-  }
-
-  #[cfg(target_os = "android")]
-  println!(
-    "cargo:rustc-link-arg-bin=deno=-Wl,--export-dynamic-symbol-list={}",
-    symbols_path.display()
-  );
-
   // To debug snapshot issues uncomment:
   // op_fetch_asset::trace_serializer();
 
diff --git a/cli/cache/cache_db.rs b/cli/cache/cache_db.rs
index b24078f29b..329ed2d970 100644
--- a/cli/cache/cache_db.rs
+++ b/cli/cache/cache_db.rs
@@ -57,7 +57,7 @@ impl rusqlite::types::FromSql for CacheDBHash {
 }
 
 /// What should the cache should do on failure?
-#[derive(Default)]
+#[derive(Debug, Default)]
 pub enum CacheFailure {
   /// Return errors if failure mode otherwise unspecified.
   #[default]
@@ -69,6 +69,7 @@ pub enum CacheFailure {
 }
 
 /// Configuration SQL and other parameters for a [`CacheDB`].
+#[derive(Debug)]
 pub struct CacheDBConfiguration {
   /// SQL to run for a new database.
   pub table_initializer: &'static str,
@@ -98,6 +99,7 @@ impl CacheDBConfiguration {
   }
 }
 
+#[derive(Debug)]
 enum ConnectionState {
   Connected(Connection),
   Blackhole,
@@ -106,7 +108,7 @@ enum ConnectionState {
 
 /// A cache database that eagerly initializes itself off-thread, preventing initialization operations
 /// from blocking the main thread.
-#[derive(Clone)]
+#[derive(Debug, Clone)]
 pub struct CacheDB {
   // TODO(mmastrac): We can probably simplify our thread-safe implementation here
   conn: Arc<Mutex<OnceCell<ConnectionState>>>,
diff --git a/cli/cache/emit.rs b/cli/cache/emit.rs
index 6807f06c10..3c9eecfcbd 100644
--- a/cli/cache/emit.rs
+++ b/cli/cache/emit.rs
@@ -10,6 +10,7 @@ use deno_core::unsync::sync::AtomicFlag;
 use super::DiskCache;
 
 /// The cache that stores previously emitted files.
+#[derive(Debug)]
 pub struct EmitCache {
   disk_cache: DiskCache,
   emit_failed_flag: AtomicFlag,
@@ -39,7 +40,7 @@ impl EmitCache {
     &self,
     specifier: &ModuleSpecifier,
     expected_source_hash: u64,
-  ) -> Option<Vec<u8>> {
+  ) -> Option<String> {
     let emit_filename = self.get_emit_filename(specifier)?;
     let bytes = self.disk_cache.get(&emit_filename).ok()?;
     self
@@ -91,6 +92,7 @@ impl EmitCache {
 
 const LAST_LINE_PREFIX: &str = "\n// denoCacheMetadata=";
 
+#[derive(Debug)]
 struct EmitFileSerializer {
   cli_version: &'static str,
 }
@@ -100,7 +102,7 @@ impl EmitFileSerializer {
     &self,
     mut bytes: Vec<u8>,
     expected_source_hash: u64,
-  ) -> Option<Vec<u8>> {
+  ) -> Option<String> {
     let last_newline_index = bytes.iter().rposition(|&b| b == b'\n')?;
     let (content, last_line) = bytes.split_at(last_newline_index);
     let hashes = last_line.strip_prefix(LAST_LINE_PREFIX.as_bytes())?;
@@ -120,7 +122,7 @@ impl EmitFileSerializer {
 
     // everything looks good, truncate and return it
     bytes.truncate(content.len());
-    Some(bytes)
+    String::from_utf8(bytes).ok()
   }
 
   pub fn serialize(&self, code: &[u8], source_hash: u64) -> Vec<u8> {
@@ -170,8 +172,6 @@ mod test {
       },
       emit_failed_flag: Default::default(),
     };
-    let to_string =
-      |bytes: Vec<u8>| -> String { String::from_utf8(bytes).unwrap() };
 
     let specifier1 =
       ModuleSpecifier::from_file_path(temp_dir.path().join("file1.ts"))
@@ -188,13 +188,10 @@ mod test {
     assert_eq!(cache.get_emit_code(&specifier1, 5), None);
     // providing the correct source hash
     assert_eq!(
-      cache.get_emit_code(&specifier1, 10).map(to_string),
+      cache.get_emit_code(&specifier1, 10),
       Some(emit_code1.clone()),
     );
-    assert_eq!(
-      cache.get_emit_code(&specifier2, 2).map(to_string),
-      Some(emit_code2)
-    );
+    assert_eq!(cache.get_emit_code(&specifier2, 2), Some(emit_code2));
 
     // try changing the cli version (should not load previous ones)
     let cache = EmitCache {
@@ -215,18 +212,12 @@ mod test {
       },
       emit_failed_flag: Default::default(),
     };
-    assert_eq!(
-      cache.get_emit_code(&specifier1, 5).map(to_string),
-      Some(emit_code1)
-    );
+    assert_eq!(cache.get_emit_code(&specifier1, 5), Some(emit_code1));
 
     // adding when already exists should not cause issue
     let emit_code3 = "asdf".to_string();
     cache.set_emit_code(&specifier1, 20, emit_code3.as_bytes());
     assert_eq!(cache.get_emit_code(&specifier1, 5), None);
-    assert_eq!(
-      cache.get_emit_code(&specifier1, 20).map(to_string),
-      Some(emit_code3)
-    );
+    assert_eq!(cache.get_emit_code(&specifier1, 20), Some(emit_code3));
   }
 }
diff --git a/cli/cache/mod.rs b/cli/cache/mod.rs
index 628502c506..50fc135ddf 100644
--- a/cli/cache/mod.rs
+++ b/cli/cache/mod.rs
@@ -8,11 +8,9 @@ use crate::file_fetcher::FetchOptions;
 use crate::file_fetcher::FetchPermissionsOptionRef;
 use crate::file_fetcher::FileFetcher;
 use crate::file_fetcher::FileOrRedirect;
-use crate::npm::CliNpmResolver;
 use crate::util::fs::atomic_write_file_with_retries;
 use crate::util::fs::atomic_write_file_with_retries_and_fs;
 use crate::util::fs::AtomicWriteFileFsAdapter;
-use crate::util::path::specifier_has_extension;
 
 use deno_ast::MediaType;
 use deno_core::futures;
@@ -22,7 +20,9 @@ use deno_graph::source::CacheInfo;
 use deno_graph::source::LoadFuture;
 use deno_graph::source::LoadResponse;
 use deno_graph::source::Loader;
+use deno_runtime::deno_fs;
 use deno_runtime::deno_permissions::PermissionsContainer;
+use node_resolver::InNpmPackageChecker;
 use std::collections::HashMap;
 use std::path::Path;
 use std::path::PathBuf;
@@ -182,28 +182,31 @@ pub struct FetchCacherOptions {
 /// A "wrapper" for the FileFetcher and DiskCache for the Deno CLI that provides
 /// a concise interface to the DENO_DIR when building module graphs.
 pub struct FetchCacher {
-  file_fetcher: Arc<FileFetcher>,
   pub file_header_overrides: HashMap<ModuleSpecifier, HashMap<String, String>>,
+  file_fetcher: Arc<FileFetcher>,
+  fs: Arc<dyn deno_fs::FileSystem>,
   global_http_cache: Arc<GlobalHttpCache>,
-  npm_resolver: Arc<dyn CliNpmResolver>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   module_info_cache: Arc<ModuleInfoCache>,
   permissions: PermissionsContainer,
-  cache_info_enabled: bool,
   is_deno_publish: bool,
+  cache_info_enabled: bool,
 }
 
 impl FetchCacher {
   pub fn new(
     file_fetcher: Arc<FileFetcher>,
+    fs: Arc<dyn deno_fs::FileSystem>,
     global_http_cache: Arc<GlobalHttpCache>,
-    npm_resolver: Arc<dyn CliNpmResolver>,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
     module_info_cache: Arc<ModuleInfoCache>,
     options: FetchCacherOptions,
   ) -> Self {
     Self {
       file_fetcher,
+      fs,
       global_http_cache,
-      npm_resolver,
+      in_npm_pkg_checker,
       module_info_cache,
       file_header_overrides: options.file_header_overrides,
       permissions: options.permissions,
@@ -258,28 +261,21 @@ impl Loader for FetchCacher {
   ) -> LoadFuture {
     use deno_graph::source::CacheSetting as LoaderCacheSetting;
 
-    if specifier.scheme() == "file" {
-      if specifier.path().contains("/node_modules/") {
-        // The specifier might be in a completely different symlinked tree than
-        // what the node_modules url is in (ex. `/my-project-1/node_modules`
-        // symlinked to `/my-project-2/node_modules`), so first we checked if the path
-        // is in a node_modules dir to avoid needlessly canonicalizing, then now compare
-        // against the canonicalized specifier.
-        let specifier =
-          crate::node::resolve_specifier_into_node_modules(specifier);
-        if self.npm_resolver.in_npm_package(&specifier) {
-          return Box::pin(futures::future::ready(Ok(Some(
-            LoadResponse::External { specifier },
-          ))));
-        }
-      }
-
-      // make local CJS modules external to the graph
-      if specifier_has_extension(specifier, "cjs") {
+    if specifier.scheme() == "file"
+      && specifier.path().contains("/node_modules/")
+    {
+      // The specifier might be in a completely different symlinked tree than
+      // what the node_modules url is in (ex. `/my-project-1/node_modules`
+      // symlinked to `/my-project-2/node_modules`), so first we checked if the path
+      // is in a node_modules dir to avoid needlessly canonicalizing, then now compare
+      // against the canonicalized specifier.
+      let specifier = crate::node::resolve_specifier_into_node_modules(
+        specifier,
+        self.fs.as_ref(),
+      );
+      if self.in_npm_pkg_checker.in_npm_package(&specifier) {
         return Box::pin(futures::future::ready(Ok(Some(
-          LoadResponse::External {
-            specifier: specifier.clone(),
-          },
+          LoadResponse::External { specifier },
         ))));
       }
     }
@@ -325,6 +321,7 @@ impl Loader for FetchCacher {
             } else {
               FetchPermissionsOptionRef::DynamicContainer(&permissions)
             },
+            maybe_auth: None,
             maybe_accept: None,
             maybe_cache_setting: maybe_cache_setting.as_ref(),
           },
diff --git a/cli/cache/module_info.rs b/cli/cache/module_info.rs
index 4dbb01c37b..060a6f4f0c 100644
--- a/cli/cache/module_info.rs
+++ b/cli/cache/module_info.rs
@@ -44,18 +44,32 @@ pub static MODULE_INFO_CACHE_DB: CacheDBConfiguration = CacheDBConfiguration {
 /// A cache of `deno_graph::ModuleInfo` objects. Using this leads to a considerable
 /// performance improvement because when it exists we can skip parsing a module for
 /// deno_graph.
+#[derive(Debug)]
 pub struct ModuleInfoCache {
   conn: CacheDB,
+  parsed_source_cache: Arc<ParsedSourceCache>,
 }
 
 impl ModuleInfoCache {
   #[cfg(test)]
-  pub fn new_in_memory(version: &'static str) -> Self {
-    Self::new(CacheDB::in_memory(&MODULE_INFO_CACHE_DB, version))
+  pub fn new_in_memory(
+    version: &'static str,
+    parsed_source_cache: Arc<ParsedSourceCache>,
+  ) -> Self {
+    Self::new(
+      CacheDB::in_memory(&MODULE_INFO_CACHE_DB, version),
+      parsed_source_cache,
+    )
   }
 
-  pub fn new(conn: CacheDB) -> Self {
-    Self { conn }
+  pub fn new(
+    conn: CacheDB,
+    parsed_source_cache: Arc<ParsedSourceCache>,
+  ) -> Self {
+    Self {
+      conn,
+      parsed_source_cache,
+    }
   }
 
   /// Useful for testing: re-create this cache DB with a different current version.
@@ -63,6 +77,7 @@ impl ModuleInfoCache {
   pub(crate) fn recreate_with_version(self, version: &'static str) -> Self {
     Self {
       conn: self.conn.recreate_with_version(version),
+      parsed_source_cache: self.parsed_source_cache,
     }
   }
 
@@ -113,13 +128,10 @@ impl ModuleInfoCache {
     Ok(())
   }
 
-  pub fn as_module_analyzer<'a>(
-    &'a self,
-    parsed_source_cache: &'a Arc<ParsedSourceCache>,
-  ) -> ModuleInfoCacheModuleAnalyzer<'a> {
+  pub fn as_module_analyzer(&self) -> ModuleInfoCacheModuleAnalyzer {
     ModuleInfoCacheModuleAnalyzer {
       module_info_cache: self,
-      parsed_source_cache,
+      parsed_source_cache: &self.parsed_source_cache,
     }
   }
 }
@@ -129,6 +141,84 @@ pub struct ModuleInfoCacheModuleAnalyzer<'a> {
   parsed_source_cache: &'a Arc<ParsedSourceCache>,
 }
 
+impl<'a> ModuleInfoCacheModuleAnalyzer<'a> {
+  fn load_cached_module_info(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    source_hash: CacheDBHash,
+  ) -> Option<ModuleInfo> {
+    match self.module_info_cache.get_module_info(
+      specifier,
+      media_type,
+      source_hash,
+    ) {
+      Ok(Some(info)) => Some(info),
+      Ok(None) => None,
+      Err(err) => {
+        log::debug!(
+          "Error loading module cache info for {}. {:#}",
+          specifier,
+          err
+        );
+        None
+      }
+    }
+  }
+
+  fn save_module_info_to_cache(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    source_hash: CacheDBHash,
+    module_info: &ModuleInfo,
+  ) {
+    if let Err(err) = self.module_info_cache.set_module_info(
+      specifier,
+      media_type,
+      source_hash,
+      module_info,
+    ) {
+      log::debug!(
+        "Error saving module cache info for {}. {:#}",
+        specifier,
+        err
+      );
+    }
+  }
+
+  pub fn analyze_sync(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    source: &Arc<str>,
+  ) -> Result<ModuleInfo, deno_ast::ParseDiagnostic> {
+    // attempt to load from the cache
+    let source_hash = CacheDBHash::from_source(source);
+    if let Some(info) =
+      self.load_cached_module_info(specifier, media_type, source_hash)
+    {
+      return Ok(info);
+    }
+
+    // otherwise, get the module info from the parsed source cache
+    let parser = self.parsed_source_cache.as_capturing_parser();
+    let analyzer = ParserModuleAnalyzer::new(&parser);
+    let module_info =
+      analyzer.analyze_sync(specifier, source.clone(), media_type)?;
+
+    // then attempt to cache it
+    self.save_module_info_to_cache(
+      specifier,
+      media_type,
+      source_hash,
+      &module_info,
+    );
+
+    Ok(module_info)
+  }
+}
+
 #[async_trait::async_trait(?Send)]
 impl<'a> deno_graph::ModuleAnalyzer for ModuleInfoCacheModuleAnalyzer<'a> {
   async fn analyze(
@@ -139,20 +229,10 @@ impl<'a> deno_graph::ModuleAnalyzer for ModuleInfoCacheModuleAnalyzer<'a> {
   ) -> Result<ModuleInfo, deno_ast::ParseDiagnostic> {
     // attempt to load from the cache
     let source_hash = CacheDBHash::from_source(&source);
-    match self.module_info_cache.get_module_info(
-      specifier,
-      media_type,
-      source_hash,
-    ) {
-      Ok(Some(info)) => return Ok(info),
-      Ok(None) => {}
-      Err(err) => {
-        log::debug!(
-          "Error loading module cache info for {}. {:#}",
-          specifier,
-          err
-        );
-      }
+    if let Some(info) =
+      self.load_cached_module_info(specifier, media_type, source_hash)
+    {
+      return Ok(info);
     }
 
     // otherwise, get the module info from the parsed source cache
@@ -169,18 +249,12 @@ impl<'a> deno_graph::ModuleAnalyzer for ModuleInfoCacheModuleAnalyzer<'a> {
     .unwrap()?;
 
     // then attempt to cache it
-    if let Err(err) = self.module_info_cache.set_module_info(
+    self.save_module_info_to_cache(
       specifier,
       media_type,
       source_hash,
       &module_info,
-    ) {
-      log::debug!(
-        "Error saving module cache info for {}. {:#}",
-        specifier,
-        err
-      );
-    }
+    );
 
     Ok(module_info)
   }
@@ -202,7 +276,7 @@ fn serialize_media_type(media_type: MediaType) -> i64 {
     Tsx => 11,
     Json => 12,
     Wasm => 13,
-    TsBuildInfo => 14,
+    Css => 14,
     SourceMap => 15,
     Unknown => 16,
   }
@@ -217,7 +291,7 @@ mod test {
 
   #[test]
   pub fn module_info_cache_general_use() {
-    let cache = ModuleInfoCache::new_in_memory("1.0.0");
+    let cache = ModuleInfoCache::new_in_memory("1.0.0", Default::default());
     let specifier1 =
       ModuleSpecifier::parse("https://localhost/mod.ts").unwrap();
     let specifier2 =
diff --git a/cli/cache/parsed_source.rs b/cli/cache/parsed_source.rs
index e956361f46..7e819ae998 100644
--- a/cli/cache/parsed_source.rs
+++ b/cli/cache/parsed_source.rs
@@ -7,9 +7,9 @@ use deno_ast::MediaType;
 use deno_ast::ModuleSpecifier;
 use deno_ast::ParsedSource;
 use deno_core::parking_lot::Mutex;
-use deno_graph::CapturingModuleParser;
-use deno_graph::DefaultModuleParser;
-use deno_graph::ModuleParser;
+use deno_graph::CapturingEsParser;
+use deno_graph::DefaultEsParser;
+use deno_graph::EsParser;
 use deno_graph::ParseOptions;
 use deno_graph::ParsedSourceStore;
 
@@ -46,7 +46,7 @@ impl<'a> LazyGraphSourceParser<'a> {
   }
 }
 
-#[derive(Default)]
+#[derive(Debug, Default)]
 pub struct ParsedSourceCache {
   sources: Mutex<HashMap<ModuleSpecifier, ParsedSource>>,
 }
@@ -57,12 +57,11 @@ impl ParsedSourceCache {
     module: &deno_graph::JsModule,
   ) -> Result<ParsedSource, deno_ast::ParseDiagnostic> {
     let parser = self.as_capturing_parser();
-    // this will conditionally parse because it's using a CapturingModuleParser
-    parser.parse_module(ParseOptions {
+    // this will conditionally parse because it's using a CapturingEsParser
+    parser.parse_program(ParseOptions {
       specifier: &module.specifier,
       source: module.source.clone(),
       media_type: module.media_type,
-      // don't bother enabling because this method is currently only used for vendoring
       scope_analysis: false,
     })
   }
@@ -86,10 +85,9 @@ impl ParsedSourceCache {
       specifier,
       source,
       media_type,
-      // don't bother enabling because this method is currently only used for emitting
       scope_analysis: false,
     };
-    DefaultModuleParser.parse_module(options)
+    DefaultEsParser.parse_program(options)
   }
 
   /// Frees the parsed source from memory.
@@ -99,8 +97,8 @@ impl ParsedSourceCache {
 
   /// Creates a parser that will reuse a ParsedSource from the store
   /// if it exists, or else parse.
-  pub fn as_capturing_parser(&self) -> CapturingModuleParser {
-    CapturingModuleParser::new(None, self)
+  pub fn as_capturing_parser(&self) -> CapturingEsParser {
+    CapturingEsParser::new(None, self)
   }
 }
 
diff --git a/cli/emit.rs b/cli/emit.rs
index b3f4a4477a..8c4f2091cf 100644
--- a/cli/emit.rs
+++ b/cli/emit.rs
@@ -3,24 +3,28 @@
 use crate::cache::EmitCache;
 use crate::cache::FastInsecureHasher;
 use crate::cache::ParsedSourceCache;
+use crate::resolver::CjsTracker;
 
+use deno_ast::ModuleKind;
 use deno_ast::SourceMapOption;
 use deno_ast::SourceRange;
 use deno_ast::SourceRanged;
 use deno_ast::SourceRangedForSpanned;
+use deno_ast::TranspileModuleOptions;
 use deno_ast::TranspileResult;
 use deno_core::error::AnyError;
 use deno_core::futures::stream::FuturesUnordered;
 use deno_core::futures::FutureExt;
 use deno_core::futures::StreamExt;
-use deno_core::ModuleCodeBytes;
 use deno_core::ModuleSpecifier;
 use deno_graph::MediaType;
 use deno_graph::Module;
 use deno_graph::ModuleGraph;
 use std::sync::Arc;
 
+#[derive(Debug)]
 pub struct Emitter {
+  cjs_tracker: Arc<CjsTracker>,
   emit_cache: Arc<EmitCache>,
   parsed_source_cache: Arc<ParsedSourceCache>,
   transpile_and_emit_options:
@@ -31,6 +35,7 @@ pub struct Emitter {
 
 impl Emitter {
   pub fn new(
+    cjs_tracker: Arc<CjsTracker>,
     emit_cache: Arc<EmitCache>,
     parsed_source_cache: Arc<ParsedSourceCache>,
     transpile_options: deno_ast::TranspileOptions,
@@ -43,6 +48,7 @@ impl Emitter {
       hasher.finish()
     };
     Self {
+      cjs_tracker,
       emit_cache,
       parsed_source_cache,
       transpile_and_emit_options: Arc::new((transpile_options, emit_options)),
@@ -60,20 +66,19 @@ impl Emitter {
         continue;
       };
 
-      let is_emittable = matches!(
-        module.media_type,
-        MediaType::TypeScript
-          | MediaType::Mts
-          | MediaType::Cts
-          | MediaType::Jsx
-          | MediaType::Tsx
-      );
-      if is_emittable {
+      if module.media_type.is_emittable() {
         futures.push(
           self
             .emit_parsed_source(
               &module.specifier,
               module.media_type,
+              ModuleKind::from_is_cjs(
+                self.cjs_tracker.is_cjs_with_known_is_script(
+                  &module.specifier,
+                  module.media_type,
+                  module.is_script,
+                )?,
+              ),
               &module.source,
             )
             .boxed_local(),
@@ -92,9 +97,10 @@ impl Emitter {
   pub fn maybe_cached_emit(
     &self,
     specifier: &ModuleSpecifier,
+    module_kind: deno_ast::ModuleKind,
     source: &str,
-  ) -> Option<Vec<u8>> {
-    let source_hash = self.get_source_hash(source);
+  ) -> Option<String> {
+    let source_hash = self.get_source_hash(module_kind, source);
     self.emit_cache.get_emit_code(specifier, source_hash)
   }
 
@@ -102,25 +108,27 @@ impl Emitter {
     &self,
     specifier: &ModuleSpecifier,
     media_type: MediaType,
+    module_kind: deno_ast::ModuleKind,
     source: &Arc<str>,
-  ) -> Result<ModuleCodeBytes, AnyError> {
+  ) -> Result<String, AnyError> {
     // Note: keep this in sync with the sync version below
     let helper = EmitParsedSourceHelper(self);
-    match helper.pre_emit_parsed_source(specifier, source) {
+    match helper.pre_emit_parsed_source(specifier, module_kind, source) {
       PreEmitResult::Cached(emitted_text) => Ok(emitted_text),
       PreEmitResult::NotCached { source_hash } => {
         let parsed_source_cache = self.parsed_source_cache.clone();
         let transpile_and_emit_options =
           self.transpile_and_emit_options.clone();
-        let transpile_result = deno_core::unsync::spawn_blocking({
+        let transpiled_source = deno_core::unsync::spawn_blocking({
           let specifier = specifier.clone();
           let source = source.clone();
           move || -> Result<_, AnyError> {
             EmitParsedSourceHelper::transpile(
               &parsed_source_cache,
               &specifier,
-              source.clone(),
               media_type,
+              module_kind,
+              source.clone(),
               &transpile_and_emit_options.0,
               &transpile_and_emit_options.1,
             )
@@ -128,11 +136,12 @@ impl Emitter {
         })
         .await
         .unwrap()?;
-        Ok(helper.post_emit_parsed_source(
+        helper.post_emit_parsed_source(
           specifier,
-          transpile_result,
+          &transpiled_source,
           source_hash,
-        ))
+        );
+        Ok(transpiled_source)
       }
     }
   }
@@ -141,26 +150,29 @@ impl Emitter {
     &self,
     specifier: &ModuleSpecifier,
     media_type: MediaType,
+    module_kind: deno_ast::ModuleKind,
     source: &Arc<str>,
-  ) -> Result<ModuleCodeBytes, AnyError> {
+  ) -> Result<String, AnyError> {
     // Note: keep this in sync with the async version above
     let helper = EmitParsedSourceHelper(self);
-    match helper.pre_emit_parsed_source(specifier, source) {
+    match helper.pre_emit_parsed_source(specifier, module_kind, source) {
       PreEmitResult::Cached(emitted_text) => Ok(emitted_text),
       PreEmitResult::NotCached { source_hash } => {
-        let transpile_result = EmitParsedSourceHelper::transpile(
+        let transpiled_source = EmitParsedSourceHelper::transpile(
           &self.parsed_source_cache,
           specifier,
-          source.clone(),
           media_type,
+          module_kind,
+          source.clone(),
           &self.transpile_and_emit_options.0,
           &self.transpile_and_emit_options.1,
         )?;
-        Ok(helper.post_emit_parsed_source(
+        helper.post_emit_parsed_source(
           specifier,
-          transpile_result,
+          &transpiled_source,
           source_hash,
-        ))
+        );
+        Ok(transpiled_source)
       }
     }
   }
@@ -169,6 +181,7 @@ impl Emitter {
   pub async fn load_and_emit_for_hmr(
     &self,
     specifier: &ModuleSpecifier,
+    module_kind: deno_ast::ModuleKind,
   ) -> Result<String, AnyError> {
     let media_type = MediaType::from_specifier(specifier);
     let source_code = tokio::fs::read_to_string(
@@ -191,9 +204,14 @@ impl Emitter {
         let mut options = self.transpile_and_emit_options.1.clone();
         options.source_map = SourceMapOption::None;
         let transpiled_source = parsed_source
-          .transpile(&self.transpile_and_emit_options.0, &options)?
-          .into_source()
-          .into_string()?;
+          .transpile(
+            &self.transpile_and_emit_options.0,
+            &deno_ast::TranspileModuleOptions {
+              module_kind: Some(module_kind),
+            },
+            &options,
+          )?
+          .into_source();
         Ok(transpiled_source.text)
       }
       MediaType::JavaScript
@@ -204,7 +222,7 @@ impl Emitter {
       | MediaType::Dcts
       | MediaType::Json
       | MediaType::Wasm
-      | MediaType::TsBuildInfo
+      | MediaType::Css
       | MediaType::SourceMap
       | MediaType::Unknown => {
         // clear this specifier from the parsed source cache as it's now out of date
@@ -217,16 +235,17 @@ impl Emitter {
   /// A hashing function that takes the source code and uses the global emit
   /// options then generates a string hash which can be stored to
   /// determine if the cached emit is valid or not.
-  fn get_source_hash(&self, source_text: &str) -> u64 {
+  fn get_source_hash(&self, module_kind: ModuleKind, source_text: &str) -> u64 {
     FastInsecureHasher::new_without_deno_version() // stored in the transpile_and_emit_options_hash
       .write_str(source_text)
       .write_u64(self.transpile_and_emit_options_hash)
+      .write_hashable(module_kind)
       .finish()
   }
 }
 
 enum PreEmitResult {
-  Cached(ModuleCodeBytes),
+  Cached(String),
   NotCached { source_hash: u64 },
 }
 
@@ -237,14 +256,15 @@ impl<'a> EmitParsedSourceHelper<'a> {
   pub fn pre_emit_parsed_source(
     &self,
     specifier: &ModuleSpecifier,
+    module_kind: deno_ast::ModuleKind,
     source: &Arc<str>,
   ) -> PreEmitResult {
-    let source_hash = self.0.get_source_hash(source);
+    let source_hash = self.0.get_source_hash(module_kind, source);
 
     if let Some(emit_code) =
       self.0.emit_cache.get_emit_code(specifier, source_hash)
     {
-      PreEmitResult::Cached(emit_code.into_boxed_slice().into())
+      PreEmitResult::Cached(emit_code)
     } else {
       PreEmitResult::NotCached { source_hash }
     }
@@ -253,25 +273,24 @@ impl<'a> EmitParsedSourceHelper<'a> {
   pub fn transpile(
     parsed_source_cache: &ParsedSourceCache,
     specifier: &ModuleSpecifier,
-    source: Arc<str>,
     media_type: MediaType,
+    module_kind: deno_ast::ModuleKind,
+    source: Arc<str>,
     transpile_options: &deno_ast::TranspileOptions,
     emit_options: &deno_ast::EmitOptions,
-  ) -> Result<TranspileResult, AnyError> {
+  ) -> Result<String, AnyError> {
     // nothing else needs the parsed source at this point, so remove from
     // the cache in order to not transpile owned
     let parsed_source = parsed_source_cache
       .remove_or_parse_module(specifier, source, media_type)?;
     ensure_no_import_assertion(&parsed_source)?;
-    Ok(parsed_source.transpile(transpile_options, emit_options)?)
-  }
-
-  pub fn post_emit_parsed_source(
-    &self,
-    specifier: &ModuleSpecifier,
-    transpile_result: TranspileResult,
-    source_hash: u64,
-  ) -> ModuleCodeBytes {
+    let transpile_result = parsed_source.transpile(
+      transpile_options,
+      &TranspileModuleOptions {
+        module_kind: Some(module_kind),
+      },
+      emit_options,
+    )?;
     let transpiled_source = match transpile_result {
       TranspileResult::Owned(source) => source,
       TranspileResult::Cloned(source) => {
@@ -280,12 +299,20 @@ impl<'a> EmitParsedSourceHelper<'a> {
       }
     };
     debug_assert!(transpiled_source.source_map.is_none());
+    Ok(transpiled_source.text)
+  }
+
+  pub fn post_emit_parsed_source(
+    &self,
+    specifier: &ModuleSpecifier,
+    transpiled_source: &str,
+    source_hash: u64,
+  ) {
     self.0.emit_cache.set_emit_code(
       specifier,
       source_hash,
-      &transpiled_source.source,
+      transpiled_source.as_bytes(),
     );
-    transpiled_source.source.into_boxed_slice().into()
   }
 }
 
@@ -317,7 +344,7 @@ fn ensure_no_import_assertion(
     deno_core::anyhow::anyhow!("{}", msg)
   }
 
-  let Some(module) = parsed_source.program_ref().as_module() else {
+  let deno_ast::ProgramRef::Module(module) = parsed_source.program_ref() else {
     return Ok(());
   };
 
diff --git a/cli/factory.rs b/cli/factory.rs
index b96a133e98..4a36c75ba2 100644
--- a/cli/factory.rs
+++ b/cli/factory.rs
@@ -11,6 +11,7 @@ use crate::args::StorageKeyResolver;
 use crate::args::TsConfigType;
 use crate::cache::Caches;
 use crate::cache::CodeCache;
+use crate::cache::DenoCacheEnvFsAdapter;
 use crate::cache::DenoDir;
 use crate::cache::DenoDirProvider;
 use crate::cache::EmitCache;
@@ -32,12 +33,16 @@ use crate::module_loader::ModuleLoadPreparer;
 use crate::node::CliCjsCodeAnalyzer;
 use crate::node::CliNodeCodeTranslator;
 use crate::npm::create_cli_npm_resolver;
+use crate::npm::create_in_npm_pkg_checker;
 use crate::npm::CliByonmNpmResolverCreateOptions;
+use crate::npm::CliManagedInNpmPkgCheckerCreateOptions;
+use crate::npm::CliManagedNpmResolverCreateOptions;
 use crate::npm::CliNpmResolver;
 use crate::npm::CliNpmResolverCreateOptions;
-use crate::npm::CliNpmResolverManagedCreateOptions;
 use crate::npm::CliNpmResolverManagedSnapshotOption;
-use crate::resolver::CjsResolutionStore;
+use crate::npm::CreateInNpmPkgCheckerOptions;
+use crate::resolver::CjsTracker;
+use crate::resolver::CjsTrackerOptions;
 use crate::resolver::CliDenoResolverFs;
 use crate::resolver::CliGraphResolver;
 use crate::resolver::CliGraphResolverOptions;
@@ -50,6 +55,7 @@ use crate::tools::check::TypeChecker;
 use crate::tools::coverage::CoverageCollector;
 use crate::tools::lint::LintRuleProvider;
 use crate::tools::run::hmr::HmrRunner;
+use crate::tsc::TypeCheckingCjsTracker;
 use crate::util::file_watcher::WatcherCommunicator;
 use crate::util::fs::canonicalize_path_maybe_not_exists;
 use crate::util::progress_bar::ProgressBar;
@@ -58,6 +64,7 @@ use crate::worker::CliMainWorkerFactory;
 use crate::worker::CliMainWorkerOptions;
 use std::path::PathBuf;
 
+use deno_cache_dir::npm::NpmCacheDir;
 use deno_config::workspace::PackageJsonDepResolution;
 use deno_config::workspace::WorkspaceResolver;
 use deno_core::error::AnyError;
@@ -67,6 +74,7 @@ use deno_core::FeatureChecker;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::DenoFsNodeResolverEnv;
 use deno_runtime::deno_node::NodeResolver;
+use deno_runtime::deno_node::PackageJsonResolver;
 use deno_runtime::deno_permissions::Permissions;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::deno_tls::rustls::RootCertStore;
@@ -76,6 +84,7 @@ use deno_runtime::inspector_server::InspectorServer;
 use deno_runtime::permissions::RuntimePermissionDescriptorParser;
 use log::warn;
 use node_resolver::analyze::NodeCodeTranslator;
+use node_resolver::InNpmPackageChecker;
 use once_cell::sync::OnceCell;
 use std::future::Future;
 use std::sync::Arc;
@@ -163,38 +172,41 @@ impl<T> Deferred<T> {
 
 #[derive(Default)]
 struct CliFactoryServices {
-  cli_options: Deferred<Arc<CliOptions>>,
+  blob_store: Deferred<Arc<BlobStore>>,
   caches: Deferred<Arc<Caches>>,
+  cjs_tracker: Deferred<Arc<CjsTracker>>,
+  cli_node_resolver: Deferred<Arc<CliNodeResolver>>,
+  cli_options: Deferred<Arc<CliOptions>>,
+  code_cache: Deferred<Arc<CodeCache>>,
+  emit_cache: Deferred<Arc<EmitCache>>,
+  emitter: Deferred<Arc<Emitter>>,
+  feature_checker: Deferred<Arc<FeatureChecker>>,
   file_fetcher: Deferred<Arc<FileFetcher>>,
+  fs: Deferred<Arc<dyn deno_fs::FileSystem>>,
   global_http_cache: Deferred<Arc<GlobalHttpCache>>,
   http_cache: Deferred<Arc<dyn HttpCache>>,
   http_client_provider: Deferred<Arc<HttpClientProvider>>,
-  emit_cache: Deferred<Arc<EmitCache>>,
-  emitter: Deferred<Arc<Emitter>>,
-  fs: Deferred<Arc<dyn deno_fs::FileSystem>>,
+  in_npm_pkg_checker: Deferred<Arc<dyn InNpmPackageChecker>>,
   main_graph_container: Deferred<Arc<MainModuleGraphContainer>>,
-  maybe_inspector_server: Deferred<Option<Arc<InspectorServer>>>,
-  root_cert_store_provider: Deferred<Arc<dyn RootCertStoreProvider>>,
-  blob_store: Deferred<Arc<BlobStore>>,
-  module_info_cache: Deferred<Arc<ModuleInfoCache>>,
-  parsed_source_cache: Deferred<Arc<ParsedSourceCache>>,
-  resolver: Deferred<Arc<CliGraphResolver>>,
   maybe_file_watcher_reporter: Deferred<Option<FileWatcherReporter>>,
+  maybe_inspector_server: Deferred<Option<Arc<InspectorServer>>>,
   module_graph_builder: Deferred<Arc<ModuleGraphBuilder>>,
   module_graph_creator: Deferred<Arc<ModuleGraphCreator>>,
+  module_info_cache: Deferred<Arc<ModuleInfoCache>>,
   module_load_preparer: Deferred<Arc<ModuleLoadPreparer>>,
   node_code_translator: Deferred<Arc<CliNodeCodeTranslator>>,
   node_resolver: Deferred<Arc<NodeResolver>>,
+  npm_cache_dir: Deferred<Arc<NpmCacheDir>>,
   npm_resolver: Deferred<Arc<dyn CliNpmResolver>>,
+  parsed_source_cache: Deferred<Arc<ParsedSourceCache>>,
   permission_desc_parser: Deferred<Arc<RuntimePermissionDescriptorParser>>,
+  pkg_json_resolver: Deferred<Arc<PackageJsonResolver>>,
+  resolver: Deferred<Arc<CliGraphResolver>>,
+  root_cert_store_provider: Deferred<Arc<dyn RootCertStoreProvider>>,
   root_permissions_container: Deferred<PermissionsContainer>,
   sloppy_imports_resolver: Deferred<Option<Arc<CliSloppyImportsResolver>>>,
   text_only_progress_bar: Deferred<ProgressBar>,
   type_checker: Deferred<Arc<TypeChecker>>,
-  cjs_resolutions: Deferred<Arc<CjsResolutionStore>>,
-  cli_node_resolver: Deferred<Arc<CliNodeResolver>>,
-  feature_checker: Deferred<Arc<FeatureChecker>>,
-  code_cache: Deferred<Arc<CodeCache>>,
   workspace_resolver: Deferred<Arc<WorkspaceResolver>>,
 }
 
@@ -351,56 +363,112 @@ impl CliFactory {
     self.services.fs.get_or_init(|| Arc::new(deno_fs::RealFs))
   }
 
+  pub fn in_npm_pkg_checker(
+    &self,
+  ) -> Result<&Arc<dyn InNpmPackageChecker>, AnyError> {
+    self.services.in_npm_pkg_checker.get_or_try_init(|| {
+      let cli_options = self.cli_options()?;
+      let options = if cli_options.use_byonm() {
+        CreateInNpmPkgCheckerOptions::Byonm
+      } else {
+        CreateInNpmPkgCheckerOptions::Managed(
+          CliManagedInNpmPkgCheckerCreateOptions {
+            root_cache_dir_url: self.npm_cache_dir()?.root_dir_url(),
+            maybe_node_modules_path: cli_options
+              .node_modules_dir_path()
+              .map(|p| p.as_path()),
+          },
+        )
+      };
+      Ok(create_in_npm_pkg_checker(options))
+    })
+  }
+
+  pub fn npm_cache_dir(&self) -> Result<&Arc<NpmCacheDir>, AnyError> {
+    self.services.npm_cache_dir.get_or_try_init(|| {
+      let fs = self.fs();
+      let global_path = self.deno_dir()?.npm_folder_path();
+      let cli_options = self.cli_options()?;
+      Ok(Arc::new(NpmCacheDir::new(
+        &DenoCacheEnvFsAdapter(fs.as_ref()),
+        global_path,
+        cli_options.npmrc().get_all_known_registries_urls(),
+      )))
+    })
+  }
+
   pub async fn npm_resolver(
     &self,
   ) -> Result<&Arc<dyn CliNpmResolver>, AnyError> {
     self
       .services
       .npm_resolver
-      .get_or_try_init_async(async {
-        let fs = self.fs();
-        let cli_options = self.cli_options()?;
-        // For `deno install` we want to force the managed resolver so it can set up `node_modules/` directory.
-        create_cli_npm_resolver(if cli_options.use_byonm() && !matches!(cli_options.sub_command(), DenoSubcommand::Install(_) | DenoSubcommand::Add(_) | DenoSubcommand::Remove(_)) {
-          CliNpmResolverCreateOptions::Byonm(CliByonmNpmResolverCreateOptions {
-            fs: CliDenoResolverFs(fs.clone()),
-            root_node_modules_dir: Some(match cli_options.node_modules_dir_path() {
-              Some(node_modules_path) => node_modules_path.to_path_buf(),
-              // path needs to be canonicalized for node resolution
-              // (node_modules_dir_path above is already canonicalized)
-              None => canonicalize_path_maybe_not_exists(cli_options.initial_cwd())?
-                .join("node_modules"),
-            }),
-          })
-        } else {
-          CliNpmResolverCreateOptions::Managed(CliNpmResolverManagedCreateOptions {
-            snapshot: match cli_options.resolve_npm_resolution_snapshot()? {
-              Some(snapshot) => {
-                CliNpmResolverManagedSnapshotOption::Specified(Some(snapshot))
-              }
-              None => match cli_options.maybe_lockfile() {
-                Some(lockfile) => {
-                  CliNpmResolverManagedSnapshotOption::ResolveFromLockfile(
-                    lockfile.clone(),
-                  )
-                }
-                None => CliNpmResolverManagedSnapshotOption::Specified(None),
+      .get_or_try_init_async(
+        async {
+          let fs = self.fs();
+          let cli_options = self.cli_options()?;
+          create_cli_npm_resolver(if cli_options.use_byonm() {
+            CliNpmResolverCreateOptions::Byonm(
+              CliByonmNpmResolverCreateOptions {
+                fs: CliDenoResolverFs(fs.clone()),
+                pkg_json_resolver: self.pkg_json_resolver().clone(),
+                root_node_modules_dir: Some(
+                  match cli_options.node_modules_dir_path() {
+                    Some(node_modules_path) => node_modules_path.to_path_buf(),
+                    // path needs to be canonicalized for node resolution
+                    // (node_modules_dir_path above is already canonicalized)
+                    None => canonicalize_path_maybe_not_exists(
+                      cli_options.initial_cwd(),
+                    )?
+                    .join("node_modules"),
+                  },
+                ),
               },
-            },
-            maybe_lockfile: cli_options.maybe_lockfile().cloned(),
-            fs: fs.clone(),
-            http_client_provider: self.http_client_provider().clone(),
-            npm_global_cache_dir: self.deno_dir()?.npm_folder_path(),
-            cache_setting: cli_options.cache_setting(),
-            text_only_progress_bar: self.text_only_progress_bar().clone(),
-            maybe_node_modules_path: cli_options.node_modules_dir_path().cloned(),
-            npm_install_deps_provider: Arc::new(NpmInstallDepsProvider::from_workspace(cli_options.workspace())),
-            npm_system_info: cli_options.npm_system_info(),
-            npmrc: cli_options.npmrc().clone(),
-            lifecycle_scripts: cli_options.lifecycle_scripts_config(),
+            )
+          } else {
+            CliNpmResolverCreateOptions::Managed(
+              CliManagedNpmResolverCreateOptions {
+                snapshot: match cli_options.resolve_npm_resolution_snapshot()? {
+                  Some(snapshot) => {
+                    CliNpmResolverManagedSnapshotOption::Specified(Some(
+                      snapshot,
+                    ))
+                  }
+                  None => match cli_options.maybe_lockfile() {
+                    Some(lockfile) => {
+                      CliNpmResolverManagedSnapshotOption::ResolveFromLockfile(
+                        lockfile.clone(),
+                      )
+                    }
+                    None => {
+                      CliNpmResolverManagedSnapshotOption::Specified(None)
+                    }
+                  },
+                },
+                maybe_lockfile: cli_options.maybe_lockfile().cloned(),
+                fs: fs.clone(),
+                http_client_provider: self.http_client_provider().clone(),
+                npm_cache_dir: self.npm_cache_dir()?.clone(),
+                cache_setting: cli_options.cache_setting(),
+                text_only_progress_bar: self.text_only_progress_bar().clone(),
+                maybe_node_modules_path: cli_options
+                  .node_modules_dir_path()
+                  .cloned(),
+                npm_install_deps_provider: Arc::new(
+                  NpmInstallDepsProvider::from_workspace(
+                    cli_options.workspace(),
+                  ),
+                ),
+                npm_system_info: cli_options.npm_system_info(),
+                npmrc: cli_options.npmrc().clone(),
+                lifecycle_scripts: cli_options.lifecycle_scripts_config(),
+              },
+            )
           })
-        }).await
-      }.boxed_local())
+          .await
+        }
+        .boxed_local(),
+      )
       .await
   }
 
@@ -505,6 +573,7 @@ impl CliFactory {
     self.services.module_info_cache.get_or_try_init(|| {
       Ok(Arc::new(ModuleInfoCache::new(
         self.caches()?.dep_analysis_db(),
+        self.parsed_source_cache().clone(),
       )))
     })
   }
@@ -533,6 +602,7 @@ impl CliFactory {
           ts_config_result.ts_config,
         )?;
       Ok(Arc::new(Emitter::new(
+        self.cjs_tracker()?.clone(),
         self.emit_cache()?.clone(),
         self.parsed_source_cache().clone(),
         transpile_options,
@@ -556,7 +626,9 @@ impl CliFactory {
         async {
           Ok(Arc::new(NodeResolver::new(
             DenoFsNodeResolverEnv::new(self.fs().clone()),
+            self.in_npm_pkg_checker()?.clone(),
             self.npm_resolver().await?.clone().into_npm_resolver(),
+            self.pkg_json_resolver().clone(),
           )))
         }
         .boxed_local(),
@@ -574,23 +646,35 @@ impl CliFactory {
         let caches = self.caches()?;
         let node_analysis_cache =
           NodeAnalysisCache::new(caches.node_analysis_db());
-        let node_resolver = self.cli_node_resolver().await?.clone();
+        let node_resolver = self.node_resolver().await?.clone();
         let cjs_esm_analyzer = CliCjsCodeAnalyzer::new(
           node_analysis_cache,
+          self.cjs_tracker()?.clone(),
           self.fs().clone(),
-          node_resolver,
+          Some(self.parsed_source_cache().clone()),
+          self.cli_options()?.is_npm_main(),
         );
 
         Ok(Arc::new(NodeCodeTranslator::new(
           cjs_esm_analyzer,
           DenoFsNodeResolverEnv::new(self.fs().clone()),
-          self.node_resolver().await?.clone(),
+          self.in_npm_pkg_checker()?.clone(),
+          node_resolver,
           self.npm_resolver().await?.clone().into_npm_resolver(),
+          self.pkg_json_resolver().clone(),
         )))
       })
       .await
   }
 
+  pub fn pkg_json_resolver(&self) -> &Arc<PackageJsonResolver> {
+    self.services.pkg_json_resolver.get_or_init(|| {
+      Arc::new(PackageJsonResolver::new(DenoFsNodeResolverEnv::new(
+        self.fs().clone(),
+      )))
+    })
+  }
+
   pub async fn type_checker(&self) -> Result<&Arc<TypeChecker>, AnyError> {
     self
       .services
@@ -599,6 +683,10 @@ impl CliFactory {
         let cli_options = self.cli_options()?;
         Ok(Arc::new(TypeChecker::new(
           self.caches()?.clone(),
+          Arc::new(TypeCheckingCjsTracker::new(
+            self.cjs_tracker()?.clone(),
+            self.module_info_cache()?.clone(),
+          )),
           cli_options.clone(),
           self.module_graph_builder().await?.clone(),
           self.node_resolver().await?.clone(),
@@ -617,17 +705,18 @@ impl CliFactory {
       .get_or_try_init_async(async {
         let cli_options = self.cli_options()?;
         Ok(Arc::new(ModuleGraphBuilder::new(
-          cli_options.clone(),
           self.caches()?.clone(),
+          cli_options.clone(),
+          self.file_fetcher()?.clone(),
           self.fs().clone(),
-          self.resolver().await?.clone(),
-          self.npm_resolver().await?.clone(),
-          self.module_info_cache()?.clone(),
-          self.parsed_source_cache().clone(),
+          self.global_http_cache()?.clone(),
+          self.in_npm_pkg_checker()?.clone(),
           cli_options.maybe_lockfile().cloned(),
           self.maybe_file_watcher_reporter().clone(),
-          self.file_fetcher()?.clone(),
-          self.global_http_cache()?.clone(),
+          self.module_info_cache()?.clone(),
+          self.npm_resolver().await?.clone(),
+          self.parsed_source_cache().clone(),
+          self.resolver().await?.clone(),
           self.root_permissions_container()?.clone(),
         )))
       })
@@ -699,8 +788,17 @@ impl CliFactory {
       .await
   }
 
-  pub fn cjs_resolutions(&self) -> &Arc<CjsResolutionStore> {
-    self.services.cjs_resolutions.get_or_init(Default::default)
+  pub fn cjs_tracker(&self) -> Result<&Arc<CjsTracker>, AnyError> {
+    self.services.cjs_tracker.get_or_try_init(|| {
+      let options = self.cli_options()?;
+      Ok(Arc::new(CjsTracker::new(
+        self.in_npm_pkg_checker()?.clone(),
+        self.pkg_json_resolver().clone(),
+        CjsTrackerOptions {
+          unstable_detect_cjs: options.unstable_detect_cjs(),
+        },
+      )))
+    })
   }
 
   pub async fn cli_node_resolver(
@@ -711,8 +809,9 @@ impl CliFactory {
       .cli_node_resolver
       .get_or_try_init_async(async {
         Ok(Arc::new(CliNodeResolver::new(
-          self.cjs_resolutions().clone(),
+          self.cjs_tracker()?.clone(),
           self.fs().clone(),
+          self.in_npm_pkg_checker()?.clone(),
           self.node_resolver().await?.clone(),
           self.npm_resolver().await?.clone(),
         )))
@@ -750,7 +849,9 @@ impl CliFactory {
   ) -> Result<DenoCompileBinaryWriter, AnyError> {
     let cli_options = self.cli_options()?;
     Ok(DenoCompileBinaryWriter::new(
+      self.cjs_tracker()?,
       self.deno_dir()?,
+      self.emitter()?,
       self.file_fetcher()?,
       self.http_client_provider(),
       self.npm_resolver().await?.as_ref(),
@@ -779,16 +880,20 @@ impl CliFactory {
     &self,
   ) -> Result<CliMainWorkerFactory, AnyError> {
     let cli_options = self.cli_options()?;
+    let fs = self.fs();
     let node_resolver = self.node_resolver().await?;
     let npm_resolver = self.npm_resolver().await?;
-    let fs = self.fs();
     let cli_node_resolver = self.cli_node_resolver().await?;
     let cli_npm_resolver = self.npm_resolver().await?.clone();
+    let in_npm_pkg_checker = self.in_npm_pkg_checker()?;
     let maybe_file_watcher_communicator = if cli_options.has_hmr() {
       Some(self.watcher_communicator.clone().unwrap())
     } else {
       None
     };
+    let node_code_translator = self.node_code_translator().await?;
+    let cjs_tracker = self.cjs_tracker()?.clone();
+    let pkg_json_resolver = self.pkg_json_resolver().clone();
 
     Ok(CliMainWorkerFactory::new(
       self.blob_store().clone(),
@@ -798,33 +903,37 @@ impl CliFactory {
         None
       },
       self.feature_checker()?.clone(),
-      self.fs().clone(),
+      fs.clone(),
       maybe_file_watcher_communicator,
       self.maybe_inspector_server()?.clone(),
       cli_options.maybe_lockfile().cloned(),
       Box::new(CliModuleLoaderFactory::new(
         cli_options,
+        cjs_tracker,
         if cli_options.code_cache_enabled() {
           Some(self.code_cache()?.clone())
         } else {
           None
         },
         self.emitter()?.clone(),
+        fs.clone(),
+        in_npm_pkg_checker.clone(),
         self.main_module_graph_container().await?.clone(),
         self.module_load_preparer().await?.clone(),
+        node_code_translator.clone(),
         cli_node_resolver.clone(),
         cli_npm_resolver.clone(),
         NpmModuleLoader::new(
-          self.cjs_resolutions().clone(),
-          self.node_code_translator().await?.clone(),
+          self.cjs_tracker()?.clone(),
           fs.clone(),
-          cli_node_resolver.clone(),
+          node_code_translator.clone(),
         ),
         self.parsed_source_cache().clone(),
         self.resolver().await?.clone(),
       )),
       node_resolver.clone(),
       npm_resolver.clone(),
+      pkg_json_resolver,
       self.root_cert_store_provider().clone(),
       self.root_permissions_container()?.clone(),
       StorageKeyResolver::from_options(cli_options),
@@ -840,8 +949,10 @@ impl CliFactory {
     let create_hmr_runner = if cli_options.has_hmr() {
       let watcher_communicator = self.watcher_communicator.clone().unwrap();
       let emitter = self.emitter()?.clone();
+      let cjs_tracker = self.cjs_tracker()?.clone();
       let fn_: crate::worker::CreateHmrRunnerCb = Box::new(move |session| {
         Box::new(HmrRunner::new(
+          cjs_tracker.clone(),
           emitter.clone(),
           session,
           watcher_communicator.clone(),
@@ -878,7 +989,6 @@ impl CliFactory {
       inspect_wait: cli_options.inspect_wait().is_some(),
       strace_ops: cli_options.strace_ops().clone(),
       is_inspecting: cli_options.is_inspecting(),
-      is_npm_main: cli_options.is_npm_main(),
       location: cli_options.location_flag().clone(),
       // if the user ran a binary command, we'll need to set process.argv[0]
       // to be the name of the binary command instead of deno
diff --git a/cli/file_fetcher.rs b/cli/file_fetcher.rs
index 69daf14954..95d778f0bb 100644
--- a/cli/file_fetcher.rs
+++ b/cli/file_fetcher.rs
@@ -24,6 +24,7 @@ use deno_graph::source::LoaderChecksum;
 use deno_path_util::url_to_file_path;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::deno_web::BlobStore;
+use http::header;
 use log::debug;
 use std::borrow::Cow;
 use std::collections::HashMap;
@@ -181,6 +182,7 @@ pub enum FetchPermissionsOptionRef<'a> {
 pub struct FetchOptions<'a> {
   pub specifier: &'a ModuleSpecifier,
   pub permissions: FetchPermissionsOptionRef<'a>,
+  pub maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
   pub maybe_accept: Option<&'a str>,
   pub maybe_cache_setting: Option<&'a CacheSetting>,
 }
@@ -333,7 +335,7 @@ impl FileFetcher {
         )
       })?;
 
-    let bytes = blob.read_all().await?;
+    let bytes = blob.read_all().await;
     let headers =
       HashMap::from([("content-type".to_string(), blob.media_type.clone())]);
 
@@ -350,6 +352,7 @@ impl FileFetcher {
     maybe_accept: Option<&str>,
     cache_setting: &CacheSetting,
     maybe_checksum: Option<&LoaderChecksum>,
+    maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
   ) -> Result<FileOrRedirect, AnyError> {
     debug!(
       "FileFetcher::fetch_remote_no_follow - specifier: {}",
@@ -442,6 +445,7 @@ impl FileFetcher {
             .as_ref()
             .map(|(_, etag)| etag.clone()),
           maybe_auth_token: maybe_auth_token.clone(),
+          maybe_auth: maybe_auth.clone(),
           maybe_progress_guard: maybe_progress_guard.as_ref(),
         })
         .await?
@@ -538,7 +542,18 @@ impl FileFetcher {
     specifier: &ModuleSpecifier,
   ) -> Result<File, AnyError> {
     self
-      .fetch_inner(specifier, FetchPermissionsOptionRef::AllowAll)
+      .fetch_inner(specifier, None, FetchPermissionsOptionRef::AllowAll)
+      .await
+  }
+
+  #[inline(always)]
+  pub async fn fetch_bypass_permissions_with_maybe_auth(
+    &self,
+    specifier: &ModuleSpecifier,
+    maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
+  ) -> Result<File, AnyError> {
+    self
+      .fetch_inner(specifier, maybe_auth, FetchPermissionsOptionRef::AllowAll)
       .await
   }
 
@@ -552,6 +567,7 @@ impl FileFetcher {
     self
       .fetch_inner(
         specifier,
+        None,
         FetchPermissionsOptionRef::StaticContainer(permissions),
       )
       .await
@@ -560,12 +576,14 @@ impl FileFetcher {
   async fn fetch_inner(
     &self,
     specifier: &ModuleSpecifier,
+    maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
     permissions: FetchPermissionsOptionRef<'_>,
   ) -> Result<File, AnyError> {
     self
       .fetch_with_options(FetchOptions {
         specifier,
         permissions,
+        maybe_auth,
         maybe_accept: None,
         maybe_cache_setting: None,
       })
@@ -585,12 +603,14 @@ impl FileFetcher {
     max_redirect: usize,
   ) -> Result<File, AnyError> {
     let mut specifier = Cow::Borrowed(options.specifier);
+    let mut maybe_auth = options.maybe_auth.clone();
     for _ in 0..=max_redirect {
       match self
         .fetch_no_follow_with_options(FetchNoFollowOptions {
           fetch_options: FetchOptions {
             specifier: &specifier,
             permissions: options.permissions,
+            maybe_auth: maybe_auth.clone(),
             maybe_accept: options.maybe_accept,
             maybe_cache_setting: options.maybe_cache_setting,
           },
@@ -602,6 +622,10 @@ impl FileFetcher {
           return Ok(file);
         }
         FileOrRedirect::Redirect(redirect_specifier) => {
+          // If we were redirected to another origin, don't send the auth header anymore.
+          if redirect_specifier.origin() != specifier.origin() {
+            maybe_auth = None;
+          }
           specifier = Cow::Owned(redirect_specifier);
         }
       }
@@ -666,6 +690,7 @@ impl FileFetcher {
           options.maybe_accept,
           options.maybe_cache_setting.unwrap_or(&self.cache_setting),
           maybe_checksum,
+          options.maybe_auth,
         )
         .await
     }
@@ -756,6 +781,7 @@ mod tests {
         FetchOptions {
           specifier,
           permissions: FetchPermissionsOptionRef::AllowAll,
+          maybe_auth: None,
           maybe_accept: None,
           maybe_cache_setting: Some(&file_fetcher.cache_setting),
         },
@@ -1255,6 +1281,7 @@ mod tests {
         FetchOptions {
           specifier: &specifier,
           permissions: FetchPermissionsOptionRef::AllowAll,
+          maybe_auth: None,
           maybe_accept: None,
           maybe_cache_setting: Some(&file_fetcher.cache_setting),
         },
@@ -1268,6 +1295,7 @@ mod tests {
         FetchOptions {
           specifier: &specifier,
           permissions: FetchPermissionsOptionRef::AllowAll,
+          maybe_auth: None,
           maybe_accept: None,
           maybe_cache_setting: Some(&file_fetcher.cache_setting),
         },
diff --git a/cli/graph_util.rs b/cli/graph_util.rs
index e2f6246e74..46257cf785 100644
--- a/cli/graph_util.rs
+++ b/cli/graph_util.rs
@@ -48,6 +48,7 @@ use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_semver::jsr::JsrDepPackageReq;
 use deno_semver::package::PackageNv;
 use import_map::ImportMapError;
+use node_resolver::InNpmPackageChecker;
 use std::collections::HashSet;
 use std::error::Error;
 use std::ops::Deref;
@@ -377,48 +378,51 @@ pub struct BuildFastCheckGraphOptions<'a> {
 }
 
 pub struct ModuleGraphBuilder {
-  options: Arc<CliOptions>,
   caches: Arc<cache::Caches>,
+  cli_options: Arc<CliOptions>,
+  file_fetcher: Arc<FileFetcher>,
   fs: Arc<dyn FileSystem>,
-  resolver: Arc<CliGraphResolver>,
-  npm_resolver: Arc<dyn CliNpmResolver>,
-  module_info_cache: Arc<ModuleInfoCache>,
-  parsed_source_cache: Arc<ParsedSourceCache>,
+  global_http_cache: Arc<GlobalHttpCache>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   lockfile: Option<Arc<CliLockfile>>,
   maybe_file_watcher_reporter: Option<FileWatcherReporter>,
-  file_fetcher: Arc<FileFetcher>,
-  global_http_cache: Arc<GlobalHttpCache>,
+  module_info_cache: Arc<ModuleInfoCache>,
+  npm_resolver: Arc<dyn CliNpmResolver>,
+  parsed_source_cache: Arc<ParsedSourceCache>,
+  resolver: Arc<CliGraphResolver>,
   root_permissions_container: PermissionsContainer,
 }
 
 impl ModuleGraphBuilder {
   #[allow(clippy::too_many_arguments)]
   pub fn new(
-    options: Arc<CliOptions>,
     caches: Arc<cache::Caches>,
+    cli_options: Arc<CliOptions>,
+    file_fetcher: Arc<FileFetcher>,
     fs: Arc<dyn FileSystem>,
-    resolver: Arc<CliGraphResolver>,
-    npm_resolver: Arc<dyn CliNpmResolver>,
-    module_info_cache: Arc<ModuleInfoCache>,
-    parsed_source_cache: Arc<ParsedSourceCache>,
+    global_http_cache: Arc<GlobalHttpCache>,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
     lockfile: Option<Arc<CliLockfile>>,
     maybe_file_watcher_reporter: Option<FileWatcherReporter>,
-    file_fetcher: Arc<FileFetcher>,
-    global_http_cache: Arc<GlobalHttpCache>,
+    module_info_cache: Arc<ModuleInfoCache>,
+    npm_resolver: Arc<dyn CliNpmResolver>,
+    parsed_source_cache: Arc<ParsedSourceCache>,
+    resolver: Arc<CliGraphResolver>,
     root_permissions_container: PermissionsContainer,
   ) -> Self {
     Self {
-      options,
       caches,
+      cli_options,
+      file_fetcher,
       fs,
-      resolver,
-      npm_resolver,
-      module_info_cache,
-      parsed_source_cache,
+      global_http_cache,
+      in_npm_pkg_checker,
       lockfile,
       maybe_file_watcher_reporter,
-      file_fetcher,
-      global_http_cache,
+      module_info_cache,
+      npm_resolver,
+      parsed_source_cache,
+      resolver,
       root_permissions_container,
     }
   }
@@ -504,13 +508,11 @@ impl ModuleGraphBuilder {
     }
 
     let maybe_imports = if options.graph_kind.include_types() {
-      self.options.to_compiler_option_types()?
+      self.cli_options.to_compiler_option_types()?
     } else {
       Vec::new()
     };
-    let analyzer = self
-      .module_info_cache
-      .as_module_analyzer(&self.parsed_source_cache);
+    let analyzer = self.module_info_cache.as_module_analyzer();
     let mut loader = match options.loader {
       Some(loader) => MutLoaderRef::Borrowed(loader),
       None => MutLoaderRef::Owned(self.create_graph_loader()),
@@ -558,7 +560,7 @@ impl ModuleGraphBuilder {
     // ensure an "npm install" is done if the user has explicitly
     // opted into using a node_modules directory
     if self
-      .options
+      .cli_options
       .node_modules_dir()?
       .map(|m| m.uses_node_modules_dir())
       .unwrap_or(false)
@@ -669,10 +671,10 @@ impl ModuleGraphBuilder {
 
     graph.build_fast_check_type_graph(
       deno_graph::BuildFastCheckTypeGraphOptions {
-        jsr_url_provider: &CliJsrUrlProvider,
+        es_parser: Some(&parser),
         fast_check_cache: fast_check_cache.as_ref().map(|c| c as _),
         fast_check_dts: false,
-        module_parser: Some(&parser),
+        jsr_url_provider: &CliJsrUrlProvider,
         resolver: Some(graph_resolver),
         npm_resolver: Some(&graph_npm_resolver),
         workspace_fast_check: options.workspace_fast_check,
@@ -692,14 +694,15 @@ impl ModuleGraphBuilder {
   ) -> cache::FetchCacher {
     cache::FetchCacher::new(
       self.file_fetcher.clone(),
+      self.fs.clone(),
       self.global_http_cache.clone(),
-      self.npm_resolver.clone(),
+      self.in_npm_pkg_checker.clone(),
       self.module_info_cache.clone(),
       cache::FetchCacherOptions {
-        file_header_overrides: self.options.resolve_file_header_overrides(),
+        file_header_overrides: self.cli_options.resolve_file_header_overrides(),
         permissions,
         is_deno_publish: matches!(
-          self.options.sub_command(),
+          self.cli_options.sub_command(),
           crate::args::DenoSubcommand::Publish { .. }
         ),
       },
@@ -726,12 +729,12 @@ impl ModuleGraphBuilder {
       &self.fs,
       roots,
       GraphValidOptions {
-        kind: if self.options.type_check_mode().is_true() {
+        kind: if self.cli_options.type_check_mode().is_true() {
           GraphKind::All
         } else {
           GraphKind::CodeOnly
         },
-        check_js: self.options.check_js(),
+        check_js: self.cli_options.check_js(),
         exit_integrity_errors: true,
       },
     )
@@ -998,7 +1001,11 @@ impl deno_graph::source::Reporter for FileWatcherReporter {
   ) {
     let mut file_paths = self.file_paths.lock();
     if specifier.scheme() == "file" {
-      file_paths.push(specifier.to_file_path().unwrap());
+      // Don't trust that the path is a valid path at this point:
+      // https://github.com/denoland/deno/issues/26209.
+      if let Ok(file_path) = specifier.to_file_path() {
+        file_paths.push(file_path);
+      }
     }
 
     if modules_done == modules_total {
diff --git a/cli/http_util.rs b/cli/http_util.rs
index cf244c525a..4b17936d68 100644
--- a/cli/http_util.rs
+++ b/cli/http_util.rs
@@ -19,6 +19,7 @@ use deno_runtime::deno_fetch;
 use deno_runtime::deno_fetch::create_http_client;
 use deno_runtime::deno_fetch::CreateHttpClientOptions;
 use deno_runtime::deno_tls::RootCertStoreProvider;
+use http::header;
 use http::header::HeaderName;
 use http::header::HeaderValue;
 use http::header::ACCEPT;
@@ -204,6 +205,7 @@ pub struct FetchOnceArgs<'a> {
   pub maybe_accept: Option<String>,
   pub maybe_etag: Option<String>,
   pub maybe_auth_token: Option<AuthToken>,
+  pub maybe_auth: Option<(header::HeaderName, header::HeaderValue)>,
   pub maybe_progress_guard: Option<&'a UpdateGuard>,
 }
 
@@ -382,6 +384,8 @@ impl HttpClient {
       request
         .headers_mut()
         .insert(AUTHORIZATION, authorization_val);
+    } else if let Some((header, value)) = args.maybe_auth {
+      request.headers_mut().insert(header, value);
     }
     if let Some(accept) = args.maybe_accept {
       let accepts_val = HeaderValue::from_str(&accept)?;
@@ -470,15 +474,23 @@ impl HttpClient {
     }
   }
 
-  pub async fn download_with_progress(
+  pub async fn download_with_progress_and_retries(
     &self,
     url: Url,
     maybe_header: Option<(HeaderName, HeaderValue)>,
     progress_guard: &UpdateGuard,
   ) -> Result<Option<Vec<u8>>, DownloadError> {
-    self
-      .download_inner(url, maybe_header, Some(progress_guard))
-      .await
+    crate::util::retry::retry(
+      || {
+        self.download_inner(
+          url.clone(),
+          maybe_header.clone(),
+          Some(progress_guard),
+        )
+      },
+      |e| matches!(e, DownloadError::BadResponse(_) | DownloadError::Fetch(_)),
+    )
+    .await
   }
 
   pub async fn get_redirected_url(
@@ -784,6 +796,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -810,6 +823,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -837,6 +851,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -858,6 +873,7 @@ mod test {
         maybe_etag: Some("33a64df551425fcc55e".to_string()),
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     assert_eq!(res.unwrap(), FetchOnceResult::NotModified);
@@ -877,6 +893,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -906,6 +923,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, _)) = result {
@@ -931,6 +949,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Redirect(url, _)) = result {
@@ -966,6 +985,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -1013,6 +1033,7 @@ mod test {
           maybe_etag: None,
           maybe_auth_token: None,
           maybe_progress_guard: None,
+          maybe_auth: None,
         })
         .await;
 
@@ -1075,6 +1096,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
 
@@ -1128,6 +1150,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -1169,6 +1192,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -1191,6 +1215,7 @@ mod test {
         maybe_etag: Some("33a64df551425fcc55e".to_string()),
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     assert_eq!(res.unwrap(), FetchOnceResult::NotModified);
@@ -1225,6 +1250,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     if let Ok(FetchOnceResult::Code(body, headers)) = result {
@@ -1254,6 +1280,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
     assert!(result.is_err());
@@ -1275,6 +1302,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
 
@@ -1298,6 +1326,7 @@ mod test {
         maybe_etag: None,
         maybe_auth_token: None,
         maybe_progress_guard: None,
+        maybe_auth: None,
       })
       .await;
 
diff --git a/cli/lsp/analysis.rs b/cli/lsp/analysis.rs
index 8c2e8bb1dc..0769c90477 100644
--- a/cli/lsp/analysis.rs
+++ b/cli/lsp/analysis.rs
@@ -18,7 +18,6 @@ use deno_lint::diagnostic::LintDiagnosticRange;
 use deno_ast::SourceRange;
 use deno_ast::SourceRangedForSpanned;
 use deno_ast::SourceTextInfo;
-use deno_core::anyhow::anyhow;
 use deno_core::error::custom_error;
 use deno_core::error::AnyError;
 use deno_core::serde::Deserialize;
@@ -37,9 +36,9 @@ use deno_semver::package::PackageReq;
 use deno_semver::package::PackageReqReference;
 use deno_semver::Version;
 use import_map::ImportMap;
-use node_resolver::NpmResolver;
 use once_cell::sync::Lazy;
 use regex::Regex;
+use std::borrow::Cow;
 use std::cmp::Ordering;
 use std::collections::HashMap;
 use std::collections::HashSet;
@@ -336,7 +335,12 @@ impl<'a> TsResponseImportMapper<'a> {
       .resolver
       .maybe_managed_npm_resolver(Some(&self.file_referrer))
     {
-      if npm_resolver.in_npm_package(specifier) {
+      let in_npm_pkg = self
+        .resolver
+        .maybe_node_resolver(Some(&self.file_referrer))
+        .map(|n| n.in_npm_package(specifier))
+        .unwrap_or(false);
+      if in_npm_pkg {
         if let Ok(Some(pkg_id)) =
           npm_resolver.resolve_pkg_id_from_specifier(specifier)
         {
@@ -598,68 +602,62 @@ pub fn fix_ts_import_changes(
 
 /// Fix tsc import code actions so that the module specifier is correct for
 /// resolution by Deno (includes the extension).
-fn fix_ts_import_action(
+fn fix_ts_import_action<'a>(
   referrer: &ModuleSpecifier,
-  action: &tsc::CodeFixAction,
+  action: &'a tsc::CodeFixAction,
   import_mapper: &TsResponseImportMapper,
-) -> Result<Option<tsc::CodeFixAction>, AnyError> {
-  if matches!(
+) -> Option<Cow<'a, tsc::CodeFixAction>> {
+  if !matches!(
     action.fix_name.as_str(),
     "import" | "fixMissingFunctionDeclaration"
   ) {
-    let change = action
+    return Some(Cow::Borrowed(action));
+  }
+  let specifier = (|| {
+    let text_change = action.changes.first()?.text_changes.first()?;
+    let captures = IMPORT_SPECIFIER_RE.captures(&text_change.new_text)?;
+    Some(captures.get(1)?.as_str())
+  })();
+  let Some(specifier) = specifier else {
+    return Some(Cow::Borrowed(action));
+  };
+  if let Some(new_specifier) =
+    import_mapper.check_unresolved_specifier(specifier, referrer)
+  {
+    let description = action.description.replace(specifier, &new_specifier);
+    let changes = action
       .changes
-      .first()
-      .ok_or_else(|| anyhow!("Unexpected action changes."))?;
-    let text_change = change
-      .text_changes
-      .first()
-      .ok_or_else(|| anyhow!("Missing text change."))?;
-    if let Some(captures) = IMPORT_SPECIFIER_RE.captures(&text_change.new_text)
-    {
-      let specifier = captures
-        .get(1)
-        .ok_or_else(|| anyhow!("Missing capture."))?
-        .as_str();
-      if let Some(new_specifier) =
-        import_mapper.check_unresolved_specifier(specifier, referrer)
-      {
-        let description = action.description.replace(specifier, &new_specifier);
-        let changes = action
-          .changes
+      .iter()
+      .map(|c| {
+        let text_changes = c
+          .text_changes
           .iter()
-          .map(|c| {
-            let text_changes = c
-              .text_changes
-              .iter()
-              .map(|tc| tsc::TextChange {
-                span: tc.span.clone(),
-                new_text: tc.new_text.replace(specifier, &new_specifier),
-              })
-              .collect();
-            tsc::FileTextChanges {
-              file_name: c.file_name.clone(),
-              text_changes,
-              is_new_file: c.is_new_file,
-            }
+          .map(|tc| tsc::TextChange {
+            span: tc.span.clone(),
+            new_text: tc.new_text.replace(specifier, &new_specifier),
           })
           .collect();
+        tsc::FileTextChanges {
+          file_name: c.file_name.clone(),
+          text_changes,
+          is_new_file: c.is_new_file,
+        }
+      })
+      .collect();
 
-        return Ok(Some(tsc::CodeFixAction {
-          description,
-          changes,
-          commands: None,
-          fix_name: action.fix_name.clone(),
-          fix_id: None,
-          fix_all_description: None,
-        }));
-      } else if !import_mapper.is_valid_import(specifier, referrer) {
-        return Ok(None);
-      }
-    }
+    Some(Cow::Owned(tsc::CodeFixAction {
+      description,
+      changes,
+      commands: None,
+      fix_name: action.fix_name.clone(),
+      fix_id: None,
+      fix_all_description: None,
+    }))
+  } else if !import_mapper.is_valid_import(specifier, referrer) {
+    None
+  } else {
+    Some(Cow::Borrowed(action))
   }
-
-  Ok(Some(action.clone()))
 }
 
 /// Determines if two TypeScript diagnostic codes are effectively equivalent.
@@ -1004,8 +1002,7 @@ impl CodeActionCollection {
       specifier,
       action,
       &language_server.get_ts_response_import_mapper(specifier),
-    )?
-    else {
+    ) else {
       return Ok(());
     };
     let edit = ts_changes_to_edit(&action.changes, language_server)?;
@@ -1027,7 +1024,7 @@ impl CodeActionCollection {
     });
     self
       .actions
-      .push(CodeActionKind::Tsc(code_action, action.clone()));
+      .push(CodeActionKind::Tsc(code_action, action.as_ref().clone()));
 
     if let Some(fix_id) = &action.fix_id {
       if let Some(CodeActionKind::Tsc(existing_fix_all, existing_action)) =
@@ -1206,14 +1203,11 @@ impl CodeActionCollection {
         }),
       );
 
-      match parsed_source.program_ref() {
-        deno_ast::swc::ast::Program::Module(module) => module
-          .body
-          .iter()
-          .find(|i| i.range().contains(&specifier_range))
-          .map(|i| text_info.line_and_column_index(i.range().start)),
-        deno_ast::swc::ast::Program::Script(_) => None,
-      }
+      parsed_source
+        .program_ref()
+        .body()
+        .find(|i| i.range().contains(&specifier_range))
+        .map(|i| text_info.line_and_column_index(i.range().start))
     }
 
     async fn deno_types_for_npm_action(
diff --git a/cli/lsp/capabilities.rs b/cli/lsp/capabilities.rs
index e93d3b7c20..5cdb1224d8 100644
--- a/cli/lsp/capabilities.rs
+++ b/cli/lsp/capabilities.rs
@@ -147,11 +147,11 @@ pub fn server_capabilities(
     moniker_provider: None,
     experimental: Some(json!({
       "denoConfigTasks": true,
-      "testingApi":true,
+      "testingApi": true,
+      "didRefreshDenoConfigurationTreeNotifications": true,
     })),
     inlay_hint_provider: Some(OneOf::Left(true)),
     position_encoding: None,
-    // TODO(nayeemrmn): Support pull-based diagnostics.
     diagnostic_provider: None,
     inline_value_provider: None,
     inline_completion_provider: None,
diff --git a/cli/lsp/client.rs b/cli/lsp/client.rs
index b3f0d64fa6..65865d5b32 100644
--- a/cli/lsp/client.rs
+++ b/cli/lsp/client.rs
@@ -92,6 +92,19 @@ impl Client {
     });
   }
 
+  pub fn send_did_refresh_deno_configuration_tree_notification(
+    &self,
+    params: lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams,
+  ) {
+    // do on a task in case the caller currently is in the lsp lock
+    let client = self.0.clone();
+    spawn(async move {
+      client
+        .send_did_refresh_deno_configuration_tree_notification(params)
+        .await;
+    });
+  }
+
   pub fn send_did_change_deno_configuration_notification(
     &self,
     params: lsp_custom::DidChangeDenoConfigurationNotificationParams,
@@ -169,6 +182,10 @@ trait ClientTrait: Send + Sync {
     params: lsp_custom::DiagnosticBatchNotificationParams,
   );
   async fn send_test_notification(&self, params: TestingNotification);
+  async fn send_did_refresh_deno_configuration_tree_notification(
+    &self,
+    params: lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams,
+  );
   async fn send_did_change_deno_configuration_notification(
     &self,
     params: lsp_custom::DidChangeDenoConfigurationNotificationParams,
@@ -249,6 +266,18 @@ impl ClientTrait for TowerClient {
     }
   }
 
+  async fn send_did_refresh_deno_configuration_tree_notification(
+    &self,
+    params: lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams,
+  ) {
+    self
+      .0
+      .send_notification::<lsp_custom::DidRefreshDenoConfigurationTreeNotification>(
+        params,
+      )
+      .await
+  }
+
   async fn send_did_change_deno_configuration_notification(
     &self,
     params: lsp_custom::DidChangeDenoConfigurationNotificationParams,
@@ -366,6 +395,12 @@ impl ClientTrait for ReplClient {
 
   async fn send_test_notification(&self, _params: TestingNotification) {}
 
+  async fn send_did_refresh_deno_configuration_tree_notification(
+    &self,
+    _params: lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams,
+  ) {
+  }
+
   async fn send_did_change_deno_configuration_notification(
     &self,
     _params: lsp_custom::DidChangeDenoConfigurationNotificationParams,
diff --git a/cli/lsp/code_lens.rs b/cli/lsp/code_lens.rs
index e117888fba..a57ca3ac9f 100644
--- a/cli/lsp/code_lens.rs
+++ b/cli/lsp/code_lens.rs
@@ -421,7 +421,7 @@ pub fn collect_test(
 ) -> Result<Vec<lsp::CodeLens>, AnyError> {
   let mut collector =
     DenoTestCollector::new(specifier.clone(), parsed_source.clone());
-  parsed_source.module().visit_with(&mut collector);
+  parsed_source.program().visit_with(&mut collector);
   Ok(collector.take())
 }
 
@@ -581,7 +581,7 @@ mod tests {
     .unwrap();
     let mut collector =
       DenoTestCollector::new(specifier, parsed_module.clone());
-    parsed_module.module().visit_with(&mut collector);
+    parsed_module.program().visit_with(&mut collector);
     assert_eq!(
       collector.take(),
       vec![
diff --git a/cli/lsp/completions.rs b/cli/lsp/completions.rs
index a040be5691..1590743b2b 100644
--- a/cli/lsp/completions.rs
+++ b/cli/lsp/completions.rs
@@ -200,15 +200,11 @@ pub async fn get_import_completions(
   {
     // completions for import map specifiers
     Some(lsp::CompletionResponse::List(completion_list))
-  } else if text.starts_with("./")
-    || text.starts_with("../")
-    || text.starts_with('/')
+  } else if let Some(completion_list) =
+    get_local_completions(specifier, &text, &range, resolver)
   {
     // completions for local relative modules
-    Some(lsp::CompletionResponse::List(CompletionList {
-      is_incomplete: false,
-      items: get_local_completions(specifier, &text, &range, resolver)?,
-    }))
+    Some(lsp::CompletionResponse::List(completion_list))
   } else if !text.is_empty() {
     // completion of modules from a module registry or cache
     check_auto_config_registry(
@@ -363,15 +359,15 @@ fn get_local_completions(
   text: &str,
   range: &lsp::Range,
   resolver: &LspResolver,
-) -> Option<Vec<lsp::CompletionItem>> {
+) -> Option<CompletionList> {
   if base.scheme() != "file" {
     return None;
   }
-  let parent = base.join(text).ok()?.join(".").ok()?;
+  let parent = &text[..text.char_indices().rfind(|(_, c)| *c == '/')?.0 + 1];
   let resolved_parent = resolver
     .as_graph_resolver(Some(base))
     .resolve(
-      parent.as_str(),
+      parent,
       &Range {
         specifier: base.clone(),
         start: deno_graph::Position::zeroed(),
@@ -381,62 +377,62 @@ fn get_local_completions(
     )
     .ok()?;
   let resolved_parent_path = url_to_file_path(&resolved_parent).ok()?;
-  let raw_parent =
-    &text[..text.char_indices().rfind(|(_, c)| *c == '/')?.0 + 1];
   if resolved_parent_path.is_dir() {
     let cwd = std::env::current_dir().ok()?;
-    let items = std::fs::read_dir(resolved_parent_path).ok()?;
-    Some(
-      items
-        .filter_map(|de| {
-          let de = de.ok()?;
-          let label = de.path().file_name()?.to_string_lossy().to_string();
-          let entry_specifier = resolve_path(de.path().to_str()?, &cwd).ok()?;
-          if entry_specifier == *base {
-            return None;
-          }
-          let full_text = format!("{raw_parent}{label}");
-          let text_edit = Some(lsp::CompletionTextEdit::Edit(lsp::TextEdit {
-            range: *range,
-            new_text: full_text.clone(),
-          }));
-          let filter_text = Some(full_text);
-          match de.file_type() {
-            Ok(file_type) if file_type.is_dir() => Some(lsp::CompletionItem {
-              label,
-              kind: Some(lsp::CompletionItemKind::FOLDER),
-              detail: Some("(local)".to_string()),
-              filter_text,
-              sort_text: Some("1".to_string()),
-              text_edit,
-              commit_characters: Some(
-                IMPORT_COMMIT_CHARS.iter().map(|&c| c.into()).collect(),
-              ),
-              ..Default::default()
-            }),
-            Ok(file_type) if file_type.is_file() => {
-              if is_importable_ext(&de.path()) {
-                Some(lsp::CompletionItem {
-                  label,
-                  kind: Some(lsp::CompletionItemKind::FILE),
-                  detail: Some("(local)".to_string()),
-                  filter_text,
-                  sort_text: Some("1".to_string()),
-                  text_edit,
-                  commit_characters: Some(
-                    IMPORT_COMMIT_CHARS.iter().map(|&c| c.into()).collect(),
-                  ),
-                  ..Default::default()
-                })
-              } else {
-                None
-              }
+    let entries = std::fs::read_dir(resolved_parent_path).ok()?;
+    let items = entries
+      .filter_map(|de| {
+        let de = de.ok()?;
+        let label = de.path().file_name()?.to_string_lossy().to_string();
+        let entry_specifier = resolve_path(de.path().to_str()?, &cwd).ok()?;
+        if entry_specifier == *base {
+          return None;
+        }
+        let full_text = format!("{parent}{label}");
+        let text_edit = Some(lsp::CompletionTextEdit::Edit(lsp::TextEdit {
+          range: *range,
+          new_text: full_text.clone(),
+        }));
+        let filter_text = Some(full_text);
+        match de.file_type() {
+          Ok(file_type) if file_type.is_dir() => Some(lsp::CompletionItem {
+            label,
+            kind: Some(lsp::CompletionItemKind::FOLDER),
+            detail: Some("(local)".to_string()),
+            filter_text,
+            sort_text: Some("1".to_string()),
+            text_edit,
+            commit_characters: Some(
+              IMPORT_COMMIT_CHARS.iter().map(|&c| c.into()).collect(),
+            ),
+            ..Default::default()
+          }),
+          Ok(file_type) if file_type.is_file() => {
+            if is_importable_ext(&de.path()) {
+              Some(lsp::CompletionItem {
+                label,
+                kind: Some(lsp::CompletionItemKind::FILE),
+                detail: Some("(local)".to_string()),
+                filter_text,
+                sort_text: Some("1".to_string()),
+                text_edit,
+                commit_characters: Some(
+                  IMPORT_COMMIT_CHARS.iter().map(|&c| c.into()).collect(),
+                ),
+                ..Default::default()
+              })
+            } else {
+              None
             }
-            _ => None,
           }
-        })
-        .collect(),
-    )
+          _ => None,
+        }
+      })
+      .collect();
+    Some(CompletionList {
+      is_incomplete: false,
+      items,
+    })
   } else {
     None
   }
@@ -921,11 +917,11 @@ mod tests {
         },
       },
       &Default::default(),
-    );
-    assert!(actual.is_some());
-    let actual = actual.unwrap();
-    assert_eq!(actual.len(), 3);
-    for item in actual {
+    )
+    .unwrap();
+    assert!(!actual.is_incomplete);
+    assert_eq!(actual.items.len(), 3);
+    for item in actual.items {
       match item.text_edit {
         Some(lsp::CompletionTextEdit::Edit(text_edit)) => {
           assert!(["./b", "./f.mjs", "./g.json"]
diff --git a/cli/lsp/config.rs b/cli/lsp/config.rs
index 07fdd3c65a..34bf64446d 100644
--- a/cli/lsp/config.rs
+++ b/cli/lsp/config.rs
@@ -41,6 +41,7 @@ use deno_runtime::deno_node::PackageJson;
 use indexmap::IndexSet;
 use lsp_types::ClientCapabilities;
 use std::collections::BTreeMap;
+use std::collections::BTreeSet;
 use std::collections::HashMap;
 use std::ops::Deref;
 use std::ops::DerefMut;
@@ -50,6 +51,8 @@ use std::sync::Arc;
 use tower_lsp::lsp_types as lsp;
 
 use super::logging::lsp_log;
+use super::lsp_custom;
+use super::urls::url_to_uri;
 use crate::args::discover_npmrc_from_workspace;
 use crate::args::has_flag_env_var;
 use crate::args::CliLockfile;
@@ -437,6 +440,8 @@ pub struct LanguagePreferences {
   pub use_aliases_for_renames: bool,
   #[serde(default)]
   pub quote_style: QuoteStyle,
+  #[serde(default)]
+  pub prefer_type_only_auto_imports: bool,
 }
 
 impl Default for LanguagePreferences {
@@ -447,6 +452,7 @@ impl Default for LanguagePreferences {
       auto_import_file_exclude_patterns: vec![],
       use_aliases_for_renames: true,
       quote_style: Default::default(),
+      prefer_type_only_auto_imports: false,
     }
   }
 }
@@ -979,7 +985,7 @@ impl Config {
       | MediaType::Tsx => Some(&workspace_settings.typescript),
       MediaType::Json
       | MediaType::Wasm
-      | MediaType::TsBuildInfo
+      | MediaType::Css
       | MediaType::SourceMap
       | MediaType::Unknown => None,
     }
@@ -1185,6 +1191,7 @@ pub struct ConfigData {
   pub resolver: Arc<WorkspaceResolver>,
   pub sloppy_imports_resolver: Option<Arc<CliSloppyImportsResolver>>,
   pub import_map_from_settings: Option<ModuleSpecifier>,
+  pub unstable: BTreeSet<String>,
   watched_files: HashMap<ModuleSpecifier, ConfigWatchedFileType>,
 }
 
@@ -1582,9 +1589,16 @@ impl ConfigData {
           .join("\n")
       );
     }
+    let unstable = member_dir
+      .workspace
+      .unstable_features()
+      .iter()
+      .chain(settings.unstable.as_deref())
+      .cloned()
+      .collect::<BTreeSet<_>>();
     let unstable_sloppy_imports = std::env::var("DENO_UNSTABLE_SLOPPY_IMPORTS")
       .is_ok()
-      || member_dir.workspace.has_unstable("sloppy-imports");
+      || unstable.contains("sloppy-imports");
     let sloppy_imports_resolver = unstable_sloppy_imports.then(|| {
       Arc::new(CliSloppyImportsResolver::new(
         SloppyImportsCachedFs::new_without_stat_cache(Arc::new(
@@ -1625,6 +1639,7 @@ impl ConfigData {
       lockfile,
       npmrc,
       import_map_from_settings,
+      unstable,
       watched_files,
     }
   }
@@ -1716,14 +1731,14 @@ impl ConfigTree {
       .unwrap_or_else(|| Arc::new(FmtConfig::new_with_base(PathBuf::from("/"))))
   }
 
-  /// Returns (scope_uri, type).
+  /// Returns (scope_url, type).
   pub fn watched_file_type(
     &self,
     specifier: &ModuleSpecifier,
   ) -> Option<(&ModuleSpecifier, ConfigWatchedFileType)> {
-    for (scope_uri, data) in self.scopes.iter() {
+    for (scope_url, data) in self.scopes.iter() {
       if let Some(typ) = data.watched_files.get(specifier) {
-        return Some((scope_uri, *typ));
+        return Some((scope_url, *typ));
       }
     }
     None
@@ -1747,6 +1762,46 @@ impl ConfigTree {
       .any(|data| data.watched_files.contains_key(specifier))
   }
 
+  pub fn to_did_refresh_params(
+    &self,
+  ) -> lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams {
+    let data = self
+      .scopes
+      .values()
+      .filter_map(|data| {
+        let workspace_root_scope_uri =
+          Some(data.member_dir.workspace.root_dir())
+            .filter(|s| *s != data.member_dir.dir_url())
+            .and_then(|s| url_to_uri(s).ok());
+        Some(lsp_custom::DenoConfigurationData {
+          scope_uri: url_to_uri(&data.scope).ok()?,
+          deno_json: data.maybe_deno_json().and_then(|c| {
+            if workspace_root_scope_uri.is_some()
+              && Some(&c.specifier)
+                == data
+                  .member_dir
+                  .workspace
+                  .root_deno_json()
+                  .map(|c| &c.specifier)
+            {
+              return None;
+            }
+            Some(lsp::TextDocumentIdentifier {
+              uri: url_to_uri(&c.specifier).ok()?,
+            })
+          }),
+          package_json: data.maybe_pkg_json().and_then(|p| {
+            Some(lsp::TextDocumentIdentifier {
+              uri: url_to_uri(&p.specifier()).ok()?,
+            })
+          }),
+          workspace_root_scope_uri,
+        })
+      })
+      .collect();
+    lsp_custom::DidRefreshDenoConfigurationTreeNotificationParams { data }
+  }
+
   pub async fn refresh(
     &mut self,
     settings: &Settings,
@@ -2209,6 +2264,7 @@ mod tests {
             auto_import_file_exclude_patterns: vec![],
             use_aliases_for_renames: true,
             quote_style: QuoteStyle::Auto,
+            prefer_type_only_auto_imports: false,
           },
           suggest: CompletionSettings {
             complete_function_calls: false,
@@ -2254,6 +2310,7 @@ mod tests {
             auto_import_file_exclude_patterns: vec![],
             use_aliases_for_renames: true,
             quote_style: QuoteStyle::Auto,
+            prefer_type_only_auto_imports: false,
           },
           suggest: CompletionSettings {
             complete_function_calls: false,
diff --git a/cli/lsp/diagnostics.rs b/cli/lsp/diagnostics.rs
index caabd3f04e..83c00d27ed 100644
--- a/cli/lsp/diagnostics.rs
+++ b/cli/lsp/diagnostics.rs
@@ -1499,7 +1499,11 @@ fn diagnose_dependency(
     .data_for_specifier(referrer_doc.file_referrer().unwrap_or(referrer))
     .and_then(|d| d.resolver.maybe_import_map());
   if let Some(import_map) = import_map {
-    if let Resolution::Ok(resolved) = &dependency.maybe_code {
+    let resolved = dependency
+      .maybe_code
+      .ok()
+      .or_else(|| dependency.maybe_type.ok());
+    if let Some(resolved) = resolved {
       if let Some(to) = import_map.lookup(&resolved.specifier, referrer) {
         if dependency_key != to {
           diagnostics.push(
diff --git a/cli/lsp/documents.rs b/cli/lsp/documents.rs
index 7d1ca6810d..8609aed05e 100644
--- a/cli/lsp/documents.rs
+++ b/cli/lsp/documents.rs
@@ -272,7 +272,7 @@ fn get_maybe_test_module_fut(
       parsed_source.specifier().clone(),
       parsed_source.text_info_lazy().clone(),
     );
-    parsed_source.module().visit_with(&mut collector);
+    parsed_source.program().visit_with(&mut collector);
     Arc::new(collector.take())
   })
   .map(Result::ok)
@@ -332,12 +332,8 @@ impl Document {
       .filter(|s| cache.is_valid_file_referrer(s))
       .cloned()
       .or(file_referrer);
-    let media_type = resolve_media_type(
-      &specifier,
-      maybe_headers.as_ref(),
-      maybe_language_id,
-      &resolver,
-    );
+    let media_type =
+      resolve_media_type(&specifier, maybe_headers.as_ref(), maybe_language_id);
     let (maybe_parsed_source, maybe_module) =
       if media_type_is_diagnosable(media_type) {
         parse_and_analyze_module(
@@ -399,7 +395,6 @@ impl Document {
       &self.specifier,
       self.maybe_headers.as_ref(),
       self.maybe_language_id,
-      &resolver,
     );
     let dependencies;
     let maybe_types_dependency;
@@ -764,14 +759,7 @@ fn resolve_media_type(
   specifier: &ModuleSpecifier,
   maybe_headers: Option<&HashMap<String, String>>,
   maybe_language_id: Option<LanguageId>,
-  resolver: &LspResolver,
 ) -> MediaType {
-  if resolver.in_node_modules(specifier) {
-    if let Some(media_type) = resolver.node_media_type(specifier) {
-      return media_type;
-    }
-  }
-
   if let Some(language_id) = maybe_language_id {
     return MediaType::from_specifier_and_content_type(
       specifier,
@@ -1561,7 +1549,7 @@ fn parse_source(
   text: Arc<str>,
   media_type: MediaType,
 ) -> ParsedSourceResult {
-  deno_ast::parse_module(deno_ast::ParseParams {
+  deno_ast::parse_program(deno_ast::ParseParams {
     specifier,
     text,
     media_type,
diff --git a/cli/lsp/language_server.rs b/cli/lsp/language_server.rs
index 8269dc8515..4fa0e3afbc 100644
--- a/cli/lsp/language_server.rs
+++ b/cli/lsp/language_server.rs
@@ -904,7 +904,7 @@ impl Inner {
             | MediaType::Tsx => {}
             MediaType::Wasm
             | MediaType::SourceMap
-            | MediaType::TsBuildInfo
+            | MediaType::Css
             | MediaType::Unknown => {
               if path.extension().and_then(|s| s.to_str()) != Some("jsonc") {
                 continue;
@@ -963,6 +963,11 @@ impl Inner {
       .tree
       .refresh(&self.config.settings, &self.workspace_files, &file_fetcher)
       .await;
+    self
+      .client
+      .send_did_refresh_deno_configuration_tree_notification(
+        self.config.tree.to_did_refresh_params(),
+      );
     for config_file in self.config.tree.config_files() {
       (|| {
         let compiler_options = config_file.to_compiler_options().ok()?.options;
@@ -1379,14 +1384,10 @@ impl Inner {
         .clone();
       fmt_options.use_tabs = Some(!params.options.insert_spaces);
       fmt_options.indent_width = Some(params.options.tab_size as u8);
-      let maybe_workspace = self
-        .config
-        .tree
-        .data_for_specifier(&specifier)
-        .map(|d| &d.member_dir.workspace);
+      let config_data = self.config.tree.data_for_specifier(&specifier);
       let unstable_options = UnstableFmtOptions {
-        component: maybe_workspace
-          .map(|w| w.has_unstable("fmt-component"))
+        component: config_data
+          .map(|d| d.unstable.contains("fmt-component"))
           .unwrap_or(false),
       };
       let document = document.clone();
@@ -3807,7 +3808,7 @@ impl Inner {
     let maybe_inlay_hints = maybe_inlay_hints.map(|hints| {
       hints
         .iter()
-        .map(|hint| hint.to_lsp(line_index.clone()))
+        .map(|hint| hint.to_lsp(line_index.clone(), self))
         .collect()
     });
     self.performance.measure(mark);
diff --git a/cli/lsp/lsp_custom.rs b/cli/lsp/lsp_custom.rs
index 5f485db7ac..b570b6d0e2 100644
--- a/cli/lsp/lsp_custom.rs
+++ b/cli/lsp/lsp_custom.rs
@@ -46,6 +46,30 @@ pub struct DiagnosticBatchNotificationParams {
   pub messages_len: usize,
 }
 
+#[derive(Debug, Deserialize, Serialize)]
+#[serde(rename_all = "camelCase")]
+pub struct DenoConfigurationData {
+  pub scope_uri: lsp::Uri,
+  pub workspace_root_scope_uri: Option<lsp::Uri>,
+  pub deno_json: Option<lsp::TextDocumentIdentifier>,
+  pub package_json: Option<lsp::TextDocumentIdentifier>,
+}
+
+#[derive(Debug, Deserialize, Serialize)]
+#[serde(rename_all = "camelCase")]
+pub struct DidRefreshDenoConfigurationTreeNotificationParams {
+  pub data: Vec<DenoConfigurationData>,
+}
+
+pub enum DidRefreshDenoConfigurationTreeNotification {}
+
+impl lsp::notification::Notification
+  for DidRefreshDenoConfigurationTreeNotification
+{
+  type Params = DidRefreshDenoConfigurationTreeNotificationParams;
+  const METHOD: &'static str = "deno/didRefreshDenoConfigurationTree";
+}
+
 #[derive(Debug, Eq, Hash, PartialEq, Copy, Clone, Deserialize, Serialize)]
 #[serde(rename_all = "camelCase")]
 pub enum DenoConfigurationChangeType {
@@ -88,13 +112,15 @@ pub struct DidChangeDenoConfigurationNotificationParams {
   pub changes: Vec<DenoConfigurationChangeEvent>,
 }
 
+// TODO(nayeemrmn): This is being replaced by
+// `DidRefreshDenoConfigurationTreeNotification` for Deno > v2.0.0. Remove it
+// soon.
 pub enum DidChangeDenoConfigurationNotification {}
 
 impl lsp::notification::Notification
   for DidChangeDenoConfigurationNotification
 {
   type Params = DidChangeDenoConfigurationNotificationParams;
-
   const METHOD: &'static str = "deno/didChangeDenoConfiguration";
 }
 
@@ -102,7 +128,6 @@ pub enum DidUpgradeCheckNotification {}
 
 impl lsp::notification::Notification for DidUpgradeCheckNotification {
   type Params = DidUpgradeCheckNotificationParams;
-
   const METHOD: &'static str = "deno/didUpgradeCheck";
 }
 
@@ -125,6 +150,5 @@ pub enum DiagnosticBatchNotification {}
 
 impl lsp::notification::Notification for DiagnosticBatchNotification {
   type Params = DiagnosticBatchNotificationParams;
-
   const METHOD: &'static str = "deno/internalTestDiagnosticBatch";
 }
diff --git a/cli/lsp/npm.rs b/cli/lsp/npm.rs
index 8bdeb7e7d8..2decfc3429 100644
--- a/cli/lsp/npm.rs
+++ b/cli/lsp/npm.rs
@@ -4,6 +4,7 @@ use dashmap::DashMap;
 use deno_core::anyhow::anyhow;
 use deno_core::error::AnyError;
 use deno_core::serde_json;
+use deno_npm::npm_rc::NpmRc;
 use deno_semver::package::PackageNv;
 use deno_semver::Version;
 use serde::Deserialize;
@@ -25,7 +26,10 @@ pub struct CliNpmSearchApi {
 
 impl CliNpmSearchApi {
   pub fn new(file_fetcher: Arc<FileFetcher>) -> Self {
-    let resolver = NpmFetchResolver::new(file_fetcher.clone());
+    let resolver = NpmFetchResolver::new(
+      file_fetcher.clone(),
+      Arc::new(NpmRc::default().as_resolved(npm_registry_url()).unwrap()),
+    );
     Self {
       file_fetcher,
       resolver,
diff --git a/cli/lsp/registries.rs b/cli/lsp/registries.rs
index 5f7ce00823..ade353e683 100644
--- a/cli/lsp/registries.rs
+++ b/cli/lsp/registries.rs
@@ -482,6 +482,7 @@ impl ModuleRegistry {
         .fetch_with_options(FetchOptions {
           specifier: &specifier,
           permissions: FetchPermissionsOptionRef::AllowAll,
+          maybe_auth: None,
           maybe_accept: Some("application/vnd.deno.reg.v2+json, application/vnd.deno.reg.v1+json;q=0.9, application/json;q=0.8"),
           maybe_cache_setting: None,
         })
diff --git a/cli/lsp/resolver.rs b/cli/lsp/resolver.rs
index c89273147a..9ce76005e5 100644
--- a/cli/lsp/resolver.rs
+++ b/cli/lsp/resolver.rs
@@ -2,6 +2,8 @@
 
 use dashmap::DashMap;
 use deno_ast::MediaType;
+use deno_ast::ParsedSource;
+use deno_cache_dir::npm::NpmCacheDir;
 use deno_cache_dir::HttpCache;
 use deno_config::workspace::PackageJsonDepResolution;
 use deno_config::workspace::WorkspaceResolver;
@@ -14,15 +16,15 @@ use deno_path_util::url_to_file_path;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::NodeResolver;
 use deno_runtime::deno_node::PackageJson;
+use deno_runtime::deno_node::PackageJsonResolver;
 use deno_semver::jsr::JsrPackageReqReference;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_semver::package::PackageNv;
 use deno_semver::package::PackageReq;
 use indexmap::IndexMap;
 use node_resolver::errors::ClosestPkgJsonError;
-use node_resolver::NodeResolution;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NodeResolutionMode;
-use node_resolver::NpmResolver;
 use std::borrow::Cow;
 use std::collections::BTreeMap;
 use std::collections::BTreeSet;
@@ -36,6 +38,7 @@ use crate::args::create_default_npmrc;
 use crate::args::CacheSetting;
 use crate::args::CliLockfile;
 use crate::args::NpmInstallDepsProvider;
+use crate::cache::DenoCacheEnvFsAdapter;
 use crate::graph_util::CliJsrUrlProvider;
 use crate::http_util::HttpClientProvider;
 use crate::lsp::config::Config;
@@ -43,26 +46,32 @@ use crate::lsp::config::ConfigData;
 use crate::lsp::logging::lsp_warn;
 use crate::npm::create_cli_npm_resolver_for_lsp;
 use crate::npm::CliByonmNpmResolverCreateOptions;
+use crate::npm::CliManagedInNpmPkgCheckerCreateOptions;
+use crate::npm::CliManagedNpmResolverCreateOptions;
 use crate::npm::CliNpmResolver;
 use crate::npm::CliNpmResolverCreateOptions;
-use crate::npm::CliNpmResolverManagedCreateOptions;
 use crate::npm::CliNpmResolverManagedSnapshotOption;
+use crate::npm::CreateInNpmPkgCheckerOptions;
 use crate::npm::ManagedCliNpmResolver;
-use crate::resolver::CjsResolutionStore;
+use crate::resolver::CjsTracker;
+use crate::resolver::CjsTrackerOptions;
 use crate::resolver::CliDenoResolverFs;
 use crate::resolver::CliGraphResolver;
 use crate::resolver::CliGraphResolverOptions;
 use crate::resolver::CliNodeResolver;
 use crate::resolver::WorkerCliNpmGraphResolver;
+use crate::tsc::into_specifier_and_media_type;
 use crate::util::progress_bar::ProgressBar;
 use crate::util::progress_bar::ProgressBarStyle;
 
 #[derive(Debug, Clone)]
 struct LspScopeResolver {
+  cjs_tracker: Option<Arc<LspCjsTracker>>,
   graph_resolver: Arc<CliGraphResolver>,
   jsr_resolver: Option<Arc<JsrCacheResolver>>,
   npm_resolver: Option<Arc<dyn CliNpmResolver>>,
   node_resolver: Option<Arc<CliNodeResolver>>,
+  pkg_json_resolver: Option<Arc<PackageJsonResolver>>,
   redirect_resolver: Option<Arc<RedirectResolver>>,
   graph_imports: Arc<IndexMap<ModuleSpecifier, GraphImport>>,
   config_data: Option<Arc<ConfigData>>,
@@ -71,10 +80,12 @@ struct LspScopeResolver {
 impl Default for LspScopeResolver {
   fn default() -> Self {
     Self {
+      cjs_tracker: None,
       graph_resolver: create_graph_resolver(None, None, None),
       jsr_resolver: None,
       npm_resolver: None,
       node_resolver: None,
+      pkg_json_resolver: None,
       redirect_resolver: None,
       graph_imports: Default::default(),
       config_data: None,
@@ -90,14 +101,35 @@ impl LspScopeResolver {
   ) -> Self {
     let mut npm_resolver = None;
     let mut node_resolver = None;
+    let mut lsp_cjs_tracker = None;
+    let fs = Arc::new(deno_fs::RealFs);
+    let pkg_json_resolver = Arc::new(PackageJsonResolver::new(
+      deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    ));
     if let Some(http_client) = http_client_provider {
       npm_resolver = create_npm_resolver(
         config_data.map(|d| d.as_ref()),
         cache,
         http_client,
+        &pkg_json_resolver,
       )
       .await;
-      node_resolver = create_node_resolver(npm_resolver.as_ref());
+      if let Some(npm_resolver) = &npm_resolver {
+        let in_npm_pkg_checker = create_in_npm_pkg_checker(npm_resolver);
+        let cjs_tracker = create_cjs_tracker(
+          in_npm_pkg_checker.clone(),
+          pkg_json_resolver.clone(),
+        );
+        lsp_cjs_tracker =
+          Some(Arc::new(LspCjsTracker::new(cjs_tracker.clone())));
+        node_resolver = Some(create_node_resolver(
+          cjs_tracker,
+          fs.clone(),
+          in_npm_pkg_checker,
+          npm_resolver,
+          pkg_json_resolver.clone(),
+        ));
+      }
     }
     let graph_resolver = create_graph_resolver(
       config_data.map(|d| d.as_ref()),
@@ -134,10 +166,12 @@ impl LspScopeResolver {
       })
       .unwrap_or_default();
     Self {
+      cjs_tracker: lsp_cjs_tracker,
       graph_resolver,
       jsr_resolver,
       npm_resolver,
       node_resolver,
+      pkg_json_resolver: Some(pkg_json_resolver),
       redirect_resolver,
       graph_imports,
       config_data: config_data.cloned(),
@@ -147,18 +181,40 @@ impl LspScopeResolver {
   fn snapshot(&self) -> Arc<Self> {
     let npm_resolver =
       self.npm_resolver.as_ref().map(|r| r.clone_snapshotted());
-    let node_resolver = create_node_resolver(npm_resolver.as_ref());
+    let fs = Arc::new(deno_fs::RealFs);
+    let pkg_json_resolver = Arc::new(PackageJsonResolver::new(
+      deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    ));
+    let mut node_resolver = None;
+    let mut lsp_cjs_tracker = None;
+    if let Some(npm_resolver) = &npm_resolver {
+      let in_npm_pkg_checker = create_in_npm_pkg_checker(npm_resolver);
+      let cjs_tracker = create_cjs_tracker(
+        in_npm_pkg_checker.clone(),
+        pkg_json_resolver.clone(),
+      );
+      lsp_cjs_tracker = Some(Arc::new(LspCjsTracker::new(cjs_tracker.clone())));
+      node_resolver = Some(create_node_resolver(
+        cjs_tracker,
+        fs,
+        in_npm_pkg_checker,
+        npm_resolver,
+        pkg_json_resolver.clone(),
+      ));
+    }
     let graph_resolver = create_graph_resolver(
       self.config_data.as_deref(),
       npm_resolver.as_ref(),
       node_resolver.as_ref(),
     );
     Arc::new(Self {
+      cjs_tracker: lsp_cjs_tracker,
       graph_resolver,
       jsr_resolver: self.jsr_resolver.clone(),
       npm_resolver,
       node_resolver,
       redirect_resolver: self.redirect_resolver.clone(),
+      pkg_json_resolver: Some(pkg_json_resolver),
       graph_imports: self.graph_imports.clone(),
       config_data: self.config_data.clone(),
     })
@@ -261,6 +317,22 @@ impl LspResolver {
     resolver.graph_resolver.create_graph_npm_resolver()
   }
 
+  pub fn maybe_cjs_tracker(
+    &self,
+    file_referrer: Option<&ModuleSpecifier>,
+  ) -> Option<&Arc<LspCjsTracker>> {
+    let resolver = self.get_scope_resolver(file_referrer);
+    resolver.cjs_tracker.as_ref()
+  }
+
+  pub fn maybe_node_resolver(
+    &self,
+    file_referrer: Option<&ModuleSpecifier>,
+  ) -> Option<&Arc<CliNodeResolver>> {
+    let resolver = self.get_scope_resolver(file_referrer);
+    resolver.node_resolver.as_ref()
+  }
+
   pub fn maybe_managed_npm_resolver(
     &self,
     file_referrer: Option<&ModuleSpecifier>,
@@ -328,7 +400,7 @@ impl LspResolver {
   ) -> Option<(ModuleSpecifier, MediaType)> {
     let resolver = self.get_scope_resolver(file_referrer);
     let node_resolver = resolver.node_resolver.as_ref()?;
-    Some(NodeResolution::into_specifier_and_media_type(Some(
+    Some(into_specifier_and_media_type(Some(
       node_resolver
         .resolve_req_reference(req_ref, referrer, NodeResolutionMode::Types)
         .ok()?,
@@ -346,14 +418,10 @@ impl LspResolver {
           .contains("/node_modules/")
     }
 
-    let global_npm_resolver = self
-      .get_scope_resolver(Some(specifier))
-      .npm_resolver
-      .as_ref()
-      .and_then(|npm_resolver| npm_resolver.as_managed())
-      .filter(|r| r.root_node_modules_path().is_none());
-    if let Some(npm_resolver) = &global_npm_resolver {
-      if npm_resolver.in_npm_package(specifier) {
+    if let Some(node_resolver) =
+      &self.get_scope_resolver(Some(specifier)).node_resolver
+    {
+      if node_resolver.in_npm_package(specifier) {
         return true;
       }
     }
@@ -361,18 +429,6 @@ impl LspResolver {
     has_node_modules_dir(specifier)
   }
 
-  pub fn node_media_type(
-    &self,
-    specifier: &ModuleSpecifier,
-  ) -> Option<MediaType> {
-    let resolver = self.get_scope_resolver(Some(specifier));
-    let node_resolver = resolver.node_resolver.as_ref()?;
-    let resolution = node_resolver
-      .url_to_node_resolution(specifier.clone())
-      .ok()?;
-    Some(NodeResolution::into_specifier_and_media_type(Some(resolution)).1)
-  }
-
   pub fn is_bare_package_json_dep(
     &self,
     specifier_text: &str,
@@ -398,10 +454,10 @@ impl LspResolver {
     referrer: &ModuleSpecifier,
   ) -> Result<Option<Arc<PackageJson>>, ClosestPkgJsonError> {
     let resolver = self.get_scope_resolver(Some(referrer));
-    let Some(node_resolver) = resolver.node_resolver.as_ref() else {
+    let Some(pkg_json_resolver) = resolver.pkg_json_resolver.as_ref() else {
       return Ok(None);
     };
-    node_resolver.get_closest_package_json(referrer)
+    pkg_json_resolver.get_closest_package_json(referrer)
   }
 
   pub fn resolve_redirects(
@@ -457,11 +513,13 @@ async fn create_npm_resolver(
   config_data: Option<&ConfigData>,
   cache: &LspCache,
   http_client_provider: &Arc<HttpClientProvider>,
+  pkg_json_resolver: &Arc<PackageJsonResolver>,
 ) -> Option<Arc<dyn CliNpmResolver>> {
   let enable_byonm = config_data.map(|d| d.byonm).unwrap_or(false);
   let options = if enable_byonm {
     CliNpmResolverCreateOptions::Byonm(CliByonmNpmResolverCreateOptions {
       fs: CliDenoResolverFs(Arc::new(deno_fs::RealFs)),
+      pkg_json_resolver: pkg_json_resolver.clone(),
       root_node_modules_dir: config_data.and_then(|config_data| {
         config_data.node_modules_dir.clone().or_else(|| {
           url_to_file_path(&config_data.scope)
@@ -471,7 +529,15 @@ async fn create_npm_resolver(
       }),
     })
   } else {
-    CliNpmResolverCreateOptions::Managed(CliNpmResolverManagedCreateOptions {
+    let npmrc = config_data
+      .and_then(|d| d.npmrc.clone())
+      .unwrap_or_else(create_default_npmrc);
+    let npm_cache_dir = Arc::new(NpmCacheDir::new(
+      &DenoCacheEnvFsAdapter(&deno_fs::RealFs),
+      cache.deno_dir().npm_folder_path(),
+      npmrc.get_all_known_registries_urls(),
+    ));
+    CliNpmResolverCreateOptions::Managed(CliManagedNpmResolverCreateOptions {
       http_client_provider: http_client_provider.clone(),
       snapshot: match config_data.and_then(|d| d.lockfile.as_ref()) {
         Some(lockfile) => {
@@ -485,7 +551,7 @@ async fn create_npm_resolver(
       // updating it. Only the cache request should update the lockfile.
       maybe_lockfile: None,
       fs: Arc::new(deno_fs::RealFs),
-      npm_global_cache_dir: cache.deno_dir().npm_folder_path(),
+      npm_cache_dir,
       // Use an "only" cache setting in order to make the
       // user do an explicit "cache" command and prevent
       // the cache from being filled with lots of packages while
@@ -496,9 +562,7 @@ async fn create_npm_resolver(
         .and_then(|d| d.node_modules_dir.clone()),
       // only used for top level install, so we can ignore this
       npm_install_deps_provider: Arc::new(NpmInstallDepsProvider::empty()),
-      npmrc: config_data
-        .and_then(|d| d.npmrc.clone())
-        .unwrap_or_else(create_default_npmrc),
+      npmrc,
       npm_system_info: NpmSystemInfo::default(),
       lifecycle_scripts: Default::default(),
     })
@@ -506,28 +570,59 @@ async fn create_npm_resolver(
   Some(create_cli_npm_resolver_for_lsp(options).await)
 }
 
+fn create_cjs_tracker(
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
+) -> Arc<CjsTracker> {
+  Arc::new(CjsTracker::new(
+    in_npm_pkg_checker,
+    pkg_json_resolver,
+    CjsTrackerOptions {
+      // todo(dsherret): support in the lsp by stabilizing the feature
+      // so that we don't have to pipe the config in here
+      unstable_detect_cjs: false,
+    },
+  ))
+}
+
+fn create_in_npm_pkg_checker(
+  npm_resolver: &Arc<dyn CliNpmResolver>,
+) -> Arc<dyn InNpmPackageChecker> {
+  crate::npm::create_in_npm_pkg_checker(match npm_resolver.as_inner() {
+    crate::npm::InnerCliNpmResolverRef::Byonm(_) => {
+      CreateInNpmPkgCheckerOptions::Byonm
+    }
+    crate::npm::InnerCliNpmResolverRef::Managed(m) => {
+      CreateInNpmPkgCheckerOptions::Managed(
+        CliManagedInNpmPkgCheckerCreateOptions {
+          root_cache_dir_url: m.global_cache_root_url(),
+          maybe_node_modules_path: m.maybe_node_modules_path(),
+        },
+      )
+    }
+  })
+}
+
 fn create_node_resolver(
-  npm_resolver: Option<&Arc<dyn CliNpmResolver>>,
-) -> Option<Arc<CliNodeResolver>> {
-  use once_cell::sync::Lazy;
-
-  // it's not ideal to share this across all scopes and to
-  // never clear it, but it's fine for the time being
-  static CJS_RESOLUTIONS: Lazy<Arc<CjsResolutionStore>> =
-    Lazy::new(Default::default);
-
-  let npm_resolver = npm_resolver?;
-  let fs = Arc::new(deno_fs::RealFs);
+  cjs_tracker: Arc<CjsTracker>,
+  fs: Arc<dyn deno_fs::FileSystem>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  npm_resolver: &Arc<dyn CliNpmResolver>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
+) -> Arc<CliNodeResolver> {
   let node_resolver_inner = Arc::new(NodeResolver::new(
     deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    in_npm_pkg_checker.clone(),
     npm_resolver.clone().into_npm_resolver(),
+    pkg_json_resolver.clone(),
   ));
-  Some(Arc::new(CliNodeResolver::new(
-    CJS_RESOLUTIONS.clone(),
+  Arc::new(CliNodeResolver::new(
+    cjs_tracker.clone(),
     fs,
+    in_npm_pkg_checker,
     node_resolver_inner,
     npm_resolver.clone(),
-  )))
+  ))
 }
 
 fn create_graph_resolver(
@@ -555,8 +650,8 @@ fn create_graph_resolver(
       workspace.to_maybe_jsx_import_source_config().ok().flatten()
     }),
     maybe_vendor_dir: config_data.and_then(|d| d.vendor_dir.as_ref()),
-    bare_node_builtins_enabled: workspace
-      .is_some_and(|workspace| workspace.has_unstable("bare-node-builtins")),
+    bare_node_builtins_enabled: config_data
+      .is_some_and(|d| d.unstable.contains("bare-node-builtins")),
     sloppy_imports_resolver: config_data
       .and_then(|d| d.sloppy_imports_resolver.clone()),
   }))
@@ -702,6 +797,45 @@ impl RedirectResolver {
   }
 }
 
+#[derive(Debug)]
+pub struct LspCjsTracker {
+  cjs_tracker: Arc<CjsTracker>,
+}
+
+impl LspCjsTracker {
+  pub fn new(cjs_tracker: Arc<CjsTracker>) -> Self {
+    Self { cjs_tracker }
+  }
+
+  pub fn is_cjs(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    maybe_parsed_source: Option<&ParsedSource>,
+  ) -> bool {
+    if let Some(module_kind) =
+      self.cjs_tracker.get_known_kind(specifier, media_type)
+    {
+      module_kind.is_cjs()
+    } else {
+      let maybe_is_script = maybe_parsed_source.map(|p| p.compute_is_script());
+      maybe_is_script
+        .and_then(|is_script| {
+          self
+            .cjs_tracker
+            .is_cjs_with_known_is_script(specifier, media_type, is_script)
+            .ok()
+        })
+        .unwrap_or_else(|| {
+          self
+            .cjs_tracker
+            .is_maybe_cjs(specifier, media_type)
+            .unwrap_or(false)
+        })
+    }
+  }
+}
+
 #[cfg(test)]
 mod tests {
   use super::*;
diff --git a/cli/lsp/testing/collectors.rs b/cli/lsp/testing/collectors.rs
index 2f2ddb8773..2dd7ec0d96 100644
--- a/cli/lsp/testing/collectors.rs
+++ b/cli/lsp/testing/collectors.rs
@@ -650,7 +650,7 @@ pub mod tests {
     .unwrap();
     let text_info = parsed_module.text_info_lazy().clone();
     let mut collector = TestCollector::new(specifier, text_info);
-    parsed_module.module().visit_with(&mut collector);
+    parsed_module.program().visit_with(&mut collector);
     collector.take()
   }
 
diff --git a/cli/lsp/tsc.rs b/cli/lsp/tsc.rs
index c8b5c47f83..5fcdb3575a 100644
--- a/cli/lsp/tsc.rs
+++ b/cli/lsp/tsc.rs
@@ -2182,6 +2182,50 @@ impl NavigateToItem {
   }
 }
 
+#[derive(Debug, Clone, Deserialize)]
+#[serde(rename_all = "camelCase")]
+pub struct InlayHintDisplayPart {
+  pub text: String,
+  pub span: Option<TextSpan>,
+  pub file: Option<String>,
+}
+
+impl InlayHintDisplayPart {
+  pub fn to_lsp(
+    &self,
+    language_server: &language_server::Inner,
+  ) -> lsp::InlayHintLabelPart {
+    let location = self.file.as_ref().map(|f| {
+      let specifier =
+        resolve_url(f).unwrap_or_else(|_| INVALID_SPECIFIER.clone());
+      let file_referrer =
+        language_server.documents.get_file_referrer(&specifier);
+      let uri = language_server
+        .url_map
+        .specifier_to_uri(&specifier, file_referrer.as_deref())
+        .unwrap_or_else(|_| INVALID_URI.clone());
+      let range = self
+        .span
+        .as_ref()
+        .and_then(|s| {
+          let asset_or_doc =
+            language_server.get_asset_or_document(&specifier).ok()?;
+          Some(s.to_range(asset_or_doc.line_index()))
+        })
+        .unwrap_or_else(|| {
+          lsp::Range::new(lsp::Position::new(0, 0), lsp::Position::new(0, 0))
+        });
+      lsp::Location { uri, range }
+    });
+    lsp::InlayHintLabelPart {
+      value: self.text.clone(),
+      tooltip: None,
+      location,
+      command: None,
+    }
+  }
+}
+
 #[derive(Debug, Clone, Deserialize)]
 pub enum InlayHintKind {
   Type,
@@ -2203,6 +2247,7 @@ impl InlayHintKind {
 #[serde(rename_all = "camelCase")]
 pub struct InlayHint {
   pub text: String,
+  pub display_parts: Option<Vec<InlayHintDisplayPart>>,
   pub position: u32,
   pub kind: InlayHintKind,
   pub whitespace_before: Option<bool>,
@@ -2210,10 +2255,23 @@ pub struct InlayHint {
 }
 
 impl InlayHint {
-  pub fn to_lsp(&self, line_index: Arc<LineIndex>) -> lsp::InlayHint {
+  pub fn to_lsp(
+    &self,
+    line_index: Arc<LineIndex>,
+    language_server: &language_server::Inner,
+  ) -> lsp::InlayHint {
     lsp::InlayHint {
       position: line_index.position_tsc(self.position.into()),
-      label: lsp::InlayHintLabel::String(self.text.clone()),
+      label: if let Some(display_parts) = &self.display_parts {
+        lsp::InlayHintLabel::LabelParts(
+          display_parts
+            .iter()
+            .map(|p| p.to_lsp(language_server))
+            .collect(),
+        )
+      } else {
+        lsp::InlayHintLabel::String(self.text.clone())
+      },
       kind: self.kind.to_lsp(),
       padding_left: self.whitespace_before,
       padding_right: self.whitespace_after,
@@ -3939,7 +3997,7 @@ pub struct OutliningSpan {
   kind: OutliningSpanKind,
 }
 
-const FOLD_END_PAIR_CHARACTERS: &[u8] = &[b'}', b']', b')', b'`'];
+const FOLD_END_PAIR_CHARACTERS: &[u8] = b"}])`";
 
 impl OutliningSpan {
   pub fn to_folding_range(
@@ -4304,14 +4362,25 @@ fn op_load<'s>(
       None
     } else {
       let asset_or_document = state.get_asset_or_document(&specifier);
-      asset_or_document.map(|doc| LoadResponse {
-        data: doc.text(),
-        script_kind: crate::tsc::as_ts_script_kind(doc.media_type()),
-        version: state.script_version(&specifier),
-        is_cjs: matches!(
-          doc.media_type(),
-          MediaType::Cjs | MediaType::Cts | MediaType::Dcts
-        ),
+      asset_or_document.map(|doc| {
+        let maybe_cjs_tracker = state
+          .state_snapshot
+          .resolver
+          .maybe_cjs_tracker(Some(&specifier));
+        LoadResponse {
+          data: doc.text(),
+          script_kind: crate::tsc::as_ts_script_kind(doc.media_type()),
+          version: state.script_version(&specifier),
+          is_cjs: maybe_cjs_tracker
+            .map(|t| {
+              t.is_cjs(
+                &specifier,
+                doc.media_type(),
+                doc.maybe_parsed_source().and_then(|p| p.as_ref().ok()),
+              )
+            })
+            .unwrap_or(false),
+        }
       })
     };
 
@@ -4892,6 +4961,10 @@ pub struct UserPreferences {
   pub allow_rename_of_import_path: Option<bool>,
   #[serde(skip_serializing_if = "Option::is_none")]
   pub auto_import_file_exclude_patterns: Option<Vec<String>>,
+  #[serde(skip_serializing_if = "Option::is_none")]
+  pub interactive_inlay_hints: Option<bool>,
+  #[serde(skip_serializing_if = "Option::is_none")]
+  pub prefer_type_only_auto_imports: Option<bool>,
 }
 
 impl UserPreferences {
@@ -4909,6 +4982,7 @@ impl UserPreferences {
       include_completions_with_snippet_text: Some(
         config.snippet_support_capable(),
       ),
+      interactive_inlay_hints: Some(true),
       provide_refactor_not_applicable_reason: Some(true),
       quote_preference: Some(fmt_config.into()),
       use_label_details_in_completion_entries: Some(true),
@@ -5013,6 +5087,9 @@ impl UserPreferences {
       } else {
         Some(language_settings.preferences.quote_style)
       },
+      prefer_type_only_auto_imports: Some(
+        language_settings.preferences.prefer_type_only_auto_imports,
+      ),
       ..base_preferences
     }
   }
@@ -6154,7 +6231,7 @@ mod tests {
     let change = changes.text_changes.first().unwrap();
     assert_eq!(
       change.new_text,
-      "import type { someLongVariable } from './b.ts'\n"
+      "import { someLongVariable } from './b.ts'\n"
     );
   }
 
diff --git a/cli/main.rs b/cli/main.rs
index ddb6078af4..04daff6700 100644
--- a/cli/main.rs
+++ b/cli/main.rs
@@ -15,7 +15,6 @@ mod js;
 mod jsr;
 mod lsp;
 mod module_loader;
-mod napi;
 mod node;
 mod npm;
 mod ops;
@@ -47,8 +46,7 @@ use deno_core::error::JsError;
 use deno_core::futures::FutureExt;
 use deno_core::unsync::JoinHandle;
 use deno_npm::resolution::SnapshotFromLockfileError;
-use deno_runtime::fmt_errors::format_js_error_with_suggestions;
-use deno_runtime::fmt_errors::FixSuggestion;
+use deno_runtime::fmt_errors::format_js_error;
 use deno_runtime::tokio_util::create_and_run_current_thread_with_maybe_metrics;
 use deno_terminal::colors;
 use factory::CliFactory;
@@ -62,6 +60,10 @@ use std::ops::Deref;
 use std::path::PathBuf;
 use std::sync::Arc;
 
+#[cfg(feature = "dhat-heap")]
+#[global_allocator]
+static ALLOC: dhat::Alloc = dhat::Alloc;
+
 /// Ensures that all subcommands return an i32 exit code and an [`AnyError`] error type.
 trait SubcommandOutput {
   fn output(self) -> Result<i32, AnyError>;
@@ -133,7 +135,7 @@ async fn run_subcommand(flags: Arc<Flags>) -> Result<i32, AnyError> {
       tools::compile::compile(flags, compile_flags).await
     }),
     DenoSubcommand::Coverage(coverage_flags) => spawn_subcommand(async {
-      tools::coverage::cover_files(flags, coverage_flags).await
+      tools::coverage::cover_files(flags, coverage_flags)
     }),
     DenoSubcommand::Fmt(fmt_flags) => {
       spawn_subcommand(
@@ -166,10 +168,10 @@ async fn run_subcommand(flags: Arc<Flags>) -> Result<i32, AnyError> {
       if std::io::stderr().is_terminal() {
         log::warn!(
           "{} command is intended to be run by text editors and IDEs and shouldn't be run manually.
-  
+
   Visit https://docs.deno.com/runtime/getting_started/setup_your_environment/ for instruction
   how to setup your favorite text editor.
-  
+
   Press Ctrl+C to exit.
         ", colors::cyan("deno lsp"));
       }
@@ -362,104 +364,12 @@ fn exit_with_message(message: &str, code: i32) -> ! {
   std::process::exit(code);
 }
 
-fn get_suggestions_for_terminal_errors(e: &JsError) -> Vec<FixSuggestion> {
-  if let Some(msg) = &e.message {
-    if msg.contains("module is not defined")
-      || msg.contains("exports is not defined")
-    {
-      return vec![
-        FixSuggestion::info(
-          "Deno does not support CommonJS modules without `.cjs` extension.",
-        ),
-        FixSuggestion::hint(
-          "Rewrite this module to ESM or change the file extension to `.cjs`.",
-        ),
-      ];
-    } else if msg.contains("openKv is not a function") {
-      return vec![
-        FixSuggestion::info("Deno.openKv() is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-kv` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("cron is not a function") {
-      return vec![
-        FixSuggestion::info("Deno.cron() is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-cron` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("WebSocketStream is not defined") {
-      return vec![
-        FixSuggestion::info("new WebSocketStream() is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-net` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("Temporal is not defined") {
-      return vec![
-        FixSuggestion::info("Temporal is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-temporal` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("BroadcastChannel is not defined") {
-      return vec![
-        FixSuggestion::info("BroadcastChannel is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-broadcast-channel` flag to enable this API.",
-        ),
-      ];
-    } else if msg.contains("window is not defined") {
-      return vec![
-        FixSuggestion::info("window global is not available in Deno 2."),
-        FixSuggestion::hint("Replace `window` with `globalThis`."),
-      ];
-    } else if msg.contains("UnsafeWindowSurface is not a constructor") {
-      return vec![
-        FixSuggestion::info("Deno.UnsafeWindowSurface is an unstable API."),
-        FixSuggestion::hint(
-          "Run again with `--unstable-webgpu` flag to enable this API.",
-        ),
-      ];
-    // Try to capture errors like:
-    // ```
-    // Uncaught Error: Cannot find module '../build/Release/canvas.node'
-    // Require stack:
-    // - /.../deno/npm/registry.npmjs.org/canvas/2.11.2/lib/bindings.js
-    // - /.../.cache/deno/npm/registry.npmjs.org/canvas/2.11.2/lib/canvas.js
-    // ```
-    } else if msg.contains("Cannot find module")
-      && msg.contains("Require stack")
-      && msg.contains(".node'")
-    {
-      return vec![
-        FixSuggestion::info_multiline(
-          &[
-            "Trying to execute an npm package using Node-API addons,",
-            "these packages require local `node_modules` directory to be present."
-          ]
-        ),
-        FixSuggestion::hint_multiline(
-          &[
-            "Add `\"nodeModulesDir\": \"auto\" option to `deno.json`, and then run",
-            "`deno install --allow-scripts=npm:<package> --entrypoint <script>` to setup `node_modules` directory."
-          ]
-        )
-      ];
-    }
-  }
-
-  vec![]
-}
-
 fn exit_for_error(error: AnyError) -> ! {
   let mut error_string = format!("{error:?}");
   let mut error_code = 1;
 
   if let Some(e) = error.downcast_ref::<JsError>() {
-    let suggestions = get_suggestions_for_terminal_errors(e);
-    error_string = format_js_error_with_suggestions(e, suggestions);
+    error_string = format_js_error(e);
   } else if let Some(SnapshotFromLockfileError::IntegrityCheckFailed(e)) =
     error.downcast_ref::<SnapshotFromLockfileError>()
   {
@@ -480,6 +390,9 @@ pub(crate) fn unstable_exit_cb(feature: &str, api_name: &str) {
 }
 
 pub fn main() {
+  #[cfg(feature = "dhat-heap")]
+  let profiler = dhat::Profiler::new_heap();
+
   setup_panic_hook();
 
   util::unix::raise_fd_limit();
@@ -500,7 +413,12 @@ pub fn main() {
     run_subcommand(Arc::new(flags)).await
   };
 
-  match create_and_run_current_thread_with_maybe_metrics(future) {
+  let result = create_and_run_current_thread_with_maybe_metrics(future);
+
+  #[cfg(feature = "dhat-heap")]
+  drop(profiler);
+
+  match result {
     Ok(exit_code) => std::process::exit(exit_code),
     Err(err) => exit_for_error(err),
   }
diff --git a/cli/mainrt.rs b/cli/mainrt.rs
index 02d58fcee1..f5b798f817 100644
--- a/cli/mainrt.rs
+++ b/cli/mainrt.rs
@@ -88,11 +88,10 @@ fn main() {
   let standalone = standalone::extract_standalone(Cow::Owned(args));
   let future = async move {
     match standalone {
-      Ok(Some(future)) => {
-        let (metadata, eszip) = future.await?;
-        util::logger::init(metadata.log_level);
-        load_env_vars(&metadata.env_vars_from_env_file);
-        let exit_code = standalone::run(eszip, metadata).await?;
+      Ok(Some(data)) => {
+        util::logger::init(data.metadata.log_level);
+        load_env_vars(&data.metadata.env_vars_from_env_file);
+        let exit_code = standalone::run(data).await?;
         std::process::exit(exit_code);
       }
       Ok(None) => Ok(()),
diff --git a/cli/module_loader.rs b/cli/module_loader.rs
index 293f41ddac..43c9e1aa07 100644
--- a/cli/module_loader.rs
+++ b/cli/module_loader.rs
@@ -2,6 +2,7 @@
 
 use std::borrow::Cow;
 use std::cell::RefCell;
+use std::path::Path;
 use std::path::PathBuf;
 use std::pin::Pin;
 use std::rc::Rc;
@@ -23,19 +24,23 @@ use crate::graph_container::ModuleGraphUpdatePermit;
 use crate::graph_util::CreateGraphOptions;
 use crate::graph_util::ModuleGraphBuilder;
 use crate::node;
+use crate::node::CliNodeCodeTranslator;
 use crate::npm::CliNpmResolver;
+use crate::resolver::CjsTracker;
 use crate::resolver::CliGraphResolver;
 use crate::resolver::CliNodeResolver;
 use crate::resolver::ModuleCodeStringSource;
+use crate::resolver::NotSupportedKindInNpmError;
 use crate::resolver::NpmModuleLoader;
 use crate::tools::check;
 use crate::tools::check::TypeChecker;
 use crate::util::progress_bar::ProgressBar;
 use crate::util::text_encoding::code_without_source_map;
 use crate::util::text_encoding::source_map_from_code;
-use crate::worker::ModuleLoaderAndSourceMapGetter;
+use crate::worker::CreateModuleLoaderResult;
 use crate::worker::ModuleLoaderFactory;
 use deno_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_core::anyhow::anyhow;
 use deno_core::anyhow::bail;
 use deno_core::anyhow::Context;
@@ -63,9 +68,12 @@ use deno_graph::Module;
 use deno_graph::ModuleGraph;
 use deno_graph::Resolution;
 use deno_runtime::code_cache;
+use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::create_host_defined_options;
+use deno_runtime::deno_node::NodeRequireLoader;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_semver::npm::NpmPackageReqReference;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NodeResolutionMode;
 
 pub struct ModuleLoadPreparer {
@@ -198,11 +206,16 @@ struct SharedCliModuleLoaderState {
   lib_worker: TsTypeLib,
   initial_cwd: PathBuf,
   is_inspecting: bool,
+  is_npm_main: bool,
   is_repl: bool,
+  cjs_tracker: Arc<CjsTracker>,
   code_cache: Option<Arc<CodeCache>>,
   emitter: Arc<Emitter>,
+  fs: Arc<dyn FileSystem>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   main_module_graph_container: Arc<MainModuleGraphContainer>,
   module_load_preparer: Arc<ModuleLoadPreparer>,
+  node_code_translator: Arc<CliNodeCodeTranslator>,
   node_resolver: Arc<CliNodeResolver>,
   npm_resolver: Arc<dyn CliNpmResolver>,
   npm_module_loader: NpmModuleLoader,
@@ -218,10 +231,14 @@ impl CliModuleLoaderFactory {
   #[allow(clippy::too_many_arguments)]
   pub fn new(
     options: &CliOptions,
+    cjs_tracker: Arc<CjsTracker>,
     code_cache: Option<Arc<CodeCache>>,
     emitter: Arc<Emitter>,
+    fs: Arc<dyn FileSystem>,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
     main_module_graph_container: Arc<MainModuleGraphContainer>,
     module_load_preparer: Arc<ModuleLoadPreparer>,
+    node_code_translator: Arc<CliNodeCodeTranslator>,
     node_resolver: Arc<CliNodeResolver>,
     npm_resolver: Arc<dyn CliNpmResolver>,
     npm_module_loader: NpmModuleLoader,
@@ -235,14 +252,19 @@ impl CliModuleLoaderFactory {
         lib_worker: options.ts_type_lib_worker(),
         initial_cwd: options.initial_cwd().to_path_buf(),
         is_inspecting: options.is_inspecting(),
+        is_npm_main: options.is_npm_main(),
         is_repl: matches!(
           options.sub_command(),
           DenoSubcommand::Repl(_) | DenoSubcommand::Jupyter(_)
         ),
+        cjs_tracker,
         code_cache,
         emitter,
+        fs,
+        in_npm_pkg_checker,
         main_module_graph_container,
         module_load_preparer,
+        node_code_translator,
         node_resolver,
         npm_resolver,
         npm_module_loader,
@@ -259,19 +281,30 @@ impl CliModuleLoaderFactory {
     is_worker: bool,
     parent_permissions: PermissionsContainer,
     permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
-    let loader = Rc::new(CliModuleLoader(Rc::new(CliModuleLoaderInner {
-      lib,
-      is_worker,
-      parent_permissions,
-      permissions,
+  ) -> CreateModuleLoaderResult {
+    let module_loader =
+      Rc::new(CliModuleLoader(Rc::new(CliModuleLoaderInner {
+        lib,
+        is_worker,
+        is_npm_main: self.shared.is_npm_main,
+        parent_permissions,
+        permissions,
+        graph_container: graph_container.clone(),
+        node_code_translator: self.shared.node_code_translator.clone(),
+        emitter: self.shared.emitter.clone(),
+        parsed_source_cache: self.shared.parsed_source_cache.clone(),
+        shared: self.shared.clone(),
+      })));
+    let node_require_loader = Rc::new(CliNodeRequireLoader::new(
+      self.shared.emitter.clone(),
+      self.shared.fs.clone(),
       graph_container,
-      emitter: self.shared.emitter.clone(),
-      parsed_source_cache: self.shared.parsed_source_cache.clone(),
-      shared: self.shared.clone(),
-    })));
-    ModuleLoaderAndSourceMapGetter {
-      module_loader: loader,
+      self.shared.in_npm_pkg_checker.clone(),
+      self.shared.npm_resolver.clone(),
+    ));
+    CreateModuleLoaderResult {
+      module_loader,
+      node_require_loader,
     }
   }
 }
@@ -280,7 +313,7 @@ impl ModuleLoaderFactory for CliModuleLoaderFactory {
   fn create_for_main(
     &self,
     root_permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
+  ) -> CreateModuleLoaderResult {
     self.create_with_lib(
       (*self.shared.main_module_graph_container).clone(),
       self.shared.lib_window,
@@ -294,7 +327,7 @@ impl ModuleLoaderFactory for CliModuleLoaderFactory {
     &self,
     parent_permissions: PermissionsContainer,
     permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
+  ) -> CreateModuleLoaderResult {
     self.create_with_lib(
       // create a fresh module graph for the worker
       WorkerModuleGraphContainer::new(Arc::new(ModuleGraph::new(
@@ -310,6 +343,7 @@ impl ModuleLoaderFactory for CliModuleLoaderFactory {
 
 struct CliModuleLoaderInner<TGraphContainer: ModuleGraphContainer> {
   lib: TsTypeLib,
+  is_npm_main: bool,
   is_worker: bool,
   /// The initial set of permissions used to resolve the static imports in the
   /// worker. These are "allow all" for main worker, and parent thread
@@ -318,6 +352,7 @@ struct CliModuleLoaderInner<TGraphContainer: ModuleGraphContainer> {
   permissions: PermissionsContainer,
   shared: Arc<SharedCliModuleLoaderState>,
   emitter: Arc<Emitter>,
+  node_code_translator: Arc<CliNodeCodeTranslator>,
   parsed_source_cache: Arc<ParsedSourceCache>,
   graph_container: TGraphContainer,
 }
@@ -331,16 +366,7 @@ impl<TGraphContainer: ModuleGraphContainer>
     maybe_referrer: Option<&ModuleSpecifier>,
     requested_module_type: RequestedModuleType,
   ) -> Result<ModuleSource, AnyError> {
-    let code_source = if let Some(result) = self
-      .shared
-      .npm_module_loader
-      .load_if_in_npm_package(specifier, maybe_referrer)
-      .await
-    {
-      result?
-    } else {
-      self.load_prepared_module(specifier, maybe_referrer).await?
-    };
+    let code_source = self.load_code_source(specifier, maybe_referrer).await?;
     let code = if self.shared.is_inspecting {
       // we need the code with the source map in order for
       // it to work with --inspect or --inspect-brk
@@ -394,6 +420,29 @@ impl<TGraphContainer: ModuleGraphContainer>
     ))
   }
 
+  async fn load_code_source(
+    &self,
+    specifier: &ModuleSpecifier,
+    maybe_referrer: Option<&ModuleSpecifier>,
+  ) -> Result<ModuleCodeStringSource, AnyError> {
+    if let Some(code_source) = self.load_prepared_module(specifier).await? {
+      return Ok(code_source);
+    }
+    if self.shared.node_resolver.in_npm_package(specifier) {
+      return self
+        .shared
+        .npm_module_loader
+        .load(specifier, maybe_referrer)
+        .await;
+    }
+
+    let mut msg = format!("Loading unprepared module: {specifier}");
+    if let Some(referrer) = maybe_referrer {
+      msg = format!("{}, imported from: {}", msg, referrer.as_str());
+    }
+    Err(anyhow!(msg))
+  }
+
   fn resolve_referrer(
     &self,
     referrer: &str,
@@ -466,15 +515,11 @@ impl<TGraphContainer: ModuleGraphContainer>
     if self.shared.is_repl {
       if let Ok(reference) = NpmPackageReqReference::from_specifier(&specifier)
       {
-        return self
-          .shared
-          .node_resolver
-          .resolve_req_reference(
-            &reference,
-            referrer,
-            NodeResolutionMode::Execution,
-          )
-          .map(|res| res.into_url());
+        return self.shared.node_resolver.resolve_req_reference(
+          &reference,
+          referrer,
+          NodeResolutionMode::Execution,
+        );
       }
     }
 
@@ -498,13 +543,15 @@ impl<TGraphContainer: ModuleGraphContainer>
           .with_context(|| {
             format!("Could not resolve '{}'.", module.nv_reference)
           })?
-          .into_url()
       }
       Some(Module::Node(module)) => module.specifier.clone(),
       Some(Module::Js(module)) => module.specifier.clone(),
       Some(Module::Json(module)) => module.specifier.clone(),
       Some(Module::External(module)) => {
-        node::resolve_specifier_into_node_modules(&module.specifier)
+        node::resolve_specifier_into_node_modules(
+          &module.specifier,
+          self.shared.fs.as_ref(),
+        )
       }
       None => specifier.into_owned(),
     };
@@ -514,71 +561,82 @@ impl<TGraphContainer: ModuleGraphContainer>
   async fn load_prepared_module(
     &self,
     specifier: &ModuleSpecifier,
-    maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Result<ModuleCodeStringSource, AnyError> {
+  ) -> Result<Option<ModuleCodeStringSource>, AnyError> {
     // Note: keep this in sync with the sync version below
     let graph = self.graph_container.graph();
-    match self.load_prepared_module_or_defer_emit(
-      &graph,
-      specifier,
-      maybe_referrer,
-    ) {
-      Ok(CodeOrDeferredEmit::Code(code_source)) => Ok(code_source),
-      Ok(CodeOrDeferredEmit::DeferredEmit {
+    match self.load_prepared_module_or_defer_emit(&graph, specifier)? {
+      Some(CodeOrDeferredEmit::Code(code_source)) => Ok(Some(code_source)),
+      Some(CodeOrDeferredEmit::DeferredEmit {
         specifier,
         media_type,
         source,
       }) => {
         let transpile_result = self
           .emitter
-          .emit_parsed_source(specifier, media_type, source)
+          .emit_parsed_source(specifier, media_type, ModuleKind::Esm, source)
           .await?;
 
         // at this point, we no longer need the parsed source in memory, so free it
         self.parsed_source_cache.free(specifier);
 
-        Ok(ModuleCodeStringSource {
-          code: ModuleSourceCode::Bytes(transpile_result),
+        Ok(Some(ModuleCodeStringSource {
+          // note: it's faster to provide a string if we know it's a string
+          code: ModuleSourceCode::String(transpile_result.into()),
           found_url: specifier.clone(),
           media_type,
-        })
+        }))
       }
-      Err(err) => Err(err),
+      Some(CodeOrDeferredEmit::Cjs {
+        specifier,
+        media_type,
+        source,
+      }) => self
+        .load_maybe_cjs(specifier, media_type, source)
+        .await
+        .map(Some),
+      None => Ok(None),
     }
   }
 
-  fn load_prepared_module_sync(
+  fn load_prepared_module_for_source_map_sync(
     &self,
     specifier: &ModuleSpecifier,
-    maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Result<ModuleCodeStringSource, AnyError> {
+  ) -> Result<Option<ModuleCodeStringSource>, AnyError> {
     // Note: keep this in sync with the async version above
     let graph = self.graph_container.graph();
-    match self.load_prepared_module_or_defer_emit(
-      &graph,
-      specifier,
-      maybe_referrer,
-    ) {
-      Ok(CodeOrDeferredEmit::Code(code_source)) => Ok(code_source),
-      Ok(CodeOrDeferredEmit::DeferredEmit {
+    match self.load_prepared_module_or_defer_emit(&graph, specifier)? {
+      Some(CodeOrDeferredEmit::Code(code_source)) => Ok(Some(code_source)),
+      Some(CodeOrDeferredEmit::DeferredEmit {
         specifier,
         media_type,
         source,
       }) => {
-        let transpile_result = self
-          .emitter
-          .emit_parsed_source_sync(specifier, media_type, source)?;
+        let transpile_result = self.emitter.emit_parsed_source_sync(
+          specifier,
+          media_type,
+          ModuleKind::Esm,
+          source,
+        )?;
 
         // at this point, we no longer need the parsed source in memory, so free it
         self.parsed_source_cache.free(specifier);
 
-        Ok(ModuleCodeStringSource {
-          code: ModuleSourceCode::Bytes(transpile_result),
+        Ok(Some(ModuleCodeStringSource {
+          // note: it's faster to provide a string if we know it's a string
+          code: ModuleSourceCode::String(transpile_result.into()),
           found_url: specifier.clone(),
           media_type,
-        })
+        }))
       }
-      Err(err) => Err(err),
+      Some(CodeOrDeferredEmit::Cjs { .. }) => {
+        self.parsed_source_cache.free(specifier);
+
+        // todo(dsherret): to make this work, we should probably just
+        // rely on the CJS export cache. At the moment this is hard because
+        // cjs export analysis is only async
+        Ok(None)
+      }
+      None => Ok(None),
     }
   }
 
@@ -586,8 +644,7 @@ impl<TGraphContainer: ModuleGraphContainer>
     &self,
     graph: &'graph ModuleGraph,
     specifier: &ModuleSpecifier,
-    maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Result<CodeOrDeferredEmit<'graph>, AnyError> {
+  ) -> Result<Option<CodeOrDeferredEmit<'graph>>, AnyError> {
     if specifier.scheme() == "node" {
       // Node built-in modules should be handled internally.
       unreachable!("Deno bug. {} was misconfigured internally.", specifier);
@@ -599,38 +656,58 @@ impl<TGraphContainer: ModuleGraphContainer>
         media_type,
         specifier,
         ..
-      })) => Ok(CodeOrDeferredEmit::Code(ModuleCodeStringSource {
+      })) => Ok(Some(CodeOrDeferredEmit::Code(ModuleCodeStringSource {
         code: ModuleSourceCode::String(source.clone().into()),
         found_url: specifier.clone(),
         media_type: *media_type,
-      })),
+      }))),
       Some(deno_graph::Module::Js(JsModule {
         source,
         media_type,
         specifier,
+        is_script,
         ..
       })) => {
+        // todo(dsherret): revert in https://github.com/denoland/deno/pull/26439
+        if self.is_npm_main && *is_script
+          || self.shared.cjs_tracker.is_cjs_with_known_is_script(
+            specifier,
+            *media_type,
+            *is_script,
+          )?
+        {
+          return Ok(Some(CodeOrDeferredEmit::Cjs {
+            specifier,
+            media_type: *media_type,
+            source,
+          }));
+        }
         let code: ModuleCodeString = match media_type {
           MediaType::JavaScript
           | MediaType::Unknown
-          | MediaType::Cjs
           | MediaType::Mjs
           | MediaType::Json => source.clone().into(),
           MediaType::Dts | MediaType::Dcts | MediaType::Dmts => {
             Default::default()
           }
-          MediaType::TypeScript
-          | MediaType::Mts
-          | MediaType::Cts
-          | MediaType::Jsx
-          | MediaType::Tsx => {
-            return Ok(CodeOrDeferredEmit::DeferredEmit {
+          MediaType::Cjs | MediaType::Cts => {
+            return Ok(Some(CodeOrDeferredEmit::Cjs {
               specifier,
               media_type: *media_type,
               source,
-            });
+            }));
           }
-          MediaType::TsBuildInfo | MediaType::Wasm | MediaType::SourceMap => {
+          MediaType::TypeScript
+          | MediaType::Mts
+          | MediaType::Jsx
+          | MediaType::Tsx => {
+            return Ok(Some(CodeOrDeferredEmit::DeferredEmit {
+              specifier,
+              media_type: *media_type,
+              source,
+            }));
+          }
+          MediaType::Css | MediaType::Wasm | MediaType::SourceMap => {
             panic!("Unexpected media type {media_type} for {specifier}")
           }
         };
@@ -638,26 +715,62 @@ impl<TGraphContainer: ModuleGraphContainer>
         // at this point, we no longer need the parsed source in memory, so free it
         self.parsed_source_cache.free(specifier);
 
-        Ok(CodeOrDeferredEmit::Code(ModuleCodeStringSource {
+        Ok(Some(CodeOrDeferredEmit::Code(ModuleCodeStringSource {
           code: ModuleSourceCode::String(code),
           found_url: specifier.clone(),
           media_type: *media_type,
-        }))
+        })))
       }
       Some(
         deno_graph::Module::External(_)
         | deno_graph::Module::Node(_)
         | deno_graph::Module::Npm(_),
       )
-      | None => {
-        let mut msg = format!("Loading unprepared module: {specifier}");
-        if let Some(referrer) = maybe_referrer {
-          msg = format!("{}, imported from: {}", msg, referrer.as_str());
-        }
-        Err(anyhow!(msg))
-      }
+      | None => Ok(None),
     }
   }
+
+  async fn load_maybe_cjs(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    original_source: &Arc<str>,
+  ) -> Result<ModuleCodeStringSource, AnyError> {
+    let js_source = if media_type.is_emittable() {
+      Cow::Owned(
+        self
+          .emitter
+          .emit_parsed_source(
+            specifier,
+            media_type,
+            ModuleKind::Cjs,
+            original_source,
+          )
+          .await?,
+      )
+    } else {
+      Cow::Borrowed(original_source.as_ref())
+    };
+    let text = self
+      .node_code_translator
+      .translate_cjs_to_esm(specifier, Some(js_source))
+      .await?;
+    // at this point, we no longer need the parsed source in memory, so free it
+    self.parsed_source_cache.free(specifier);
+    Ok(ModuleCodeStringSource {
+      code: match text {
+        // perf: if the text is borrowed, that means it didn't make any changes
+        // to the original source, so we can just provide that instead of cloning
+        // the borrowed text
+        Cow::Borrowed(_) => {
+          ModuleSourceCode::String(original_source.clone().into())
+        }
+        Cow::Owned(text) => ModuleSourceCode::String(text.into()),
+      },
+      found_url: specifier.clone(),
+      media_type,
+    })
+  }
 }
 
 enum CodeOrDeferredEmit<'a> {
@@ -667,6 +780,11 @@ enum CodeOrDeferredEmit<'a> {
     media_type: MediaType,
     source: &'a Arc<str>,
   },
+  Cjs {
+    specifier: &'a ModuleSpecifier,
+    media_type: MediaType,
+    source: &'a Arc<str>,
+  },
 }
 
 // todo(dsherret): this double Rc boxing is not ideal
@@ -828,7 +946,10 @@ impl<TGraphContainer: ModuleGraphContainer> ModuleLoader
       "wasm" | "file" | "http" | "https" | "data" | "blob" => (),
       _ => return None,
     }
-    let source = self.0.load_prepared_module_sync(&specifier, None).ok()?;
+    let source = self
+      .0
+      .load_prepared_module_for_source_map_sync(&specifier)
+      .ok()??;
     source_map_from_code(source.code.as_bytes())
   }
 
@@ -907,3 +1028,79 @@ impl ModuleGraphUpdatePermit for WorkerModuleGraphUpdatePermit {
     drop(self.permit); // explicit drop for clarity
   }
 }
+
+#[derive(Debug)]
+struct CliNodeRequireLoader<TGraphContainer: ModuleGraphContainer> {
+  emitter: Arc<Emitter>,
+  fs: Arc<dyn FileSystem>,
+  graph_container: TGraphContainer,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  npm_resolver: Arc<dyn CliNpmResolver>,
+}
+
+impl<TGraphContainer: ModuleGraphContainer>
+  CliNodeRequireLoader<TGraphContainer>
+{
+  pub fn new(
+    emitter: Arc<Emitter>,
+    fs: Arc<dyn FileSystem>,
+    graph_container: TGraphContainer,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+    npm_resolver: Arc<dyn CliNpmResolver>,
+  ) -> Self {
+    Self {
+      emitter,
+      fs,
+      graph_container,
+      in_npm_pkg_checker,
+      npm_resolver,
+    }
+  }
+}
+
+impl<TGraphContainer: ModuleGraphContainer> NodeRequireLoader
+  for CliNodeRequireLoader<TGraphContainer>
+{
+  fn ensure_read_permission<'a>(
+    &self,
+    permissions: &mut dyn deno_runtime::deno_node::NodePermissions,
+    path: &'a Path,
+  ) -> Result<std::borrow::Cow<'a, Path>, AnyError> {
+    if let Ok(url) = deno_path_util::url_from_file_path(path) {
+      // allow reading if it's in the module graph
+      if self.graph_container.graph().get(&url).is_some() {
+        return Ok(std::borrow::Cow::Borrowed(path));
+      }
+    }
+    self.npm_resolver.ensure_read_permission(permissions, path)
+  }
+
+  fn load_text_file_lossy(&self, path: &Path) -> Result<String, AnyError> {
+    // todo(dsherret): use the preloaded module from the graph if available?
+    let media_type = MediaType::from_path(path);
+    let text = self.fs.read_text_file_lossy_sync(path, None)?;
+    if media_type.is_emittable() {
+      let specifier = deno_path_util::url_from_file_path(path)?;
+      if self.in_npm_pkg_checker.in_npm_package(&specifier) {
+        return Err(
+          NotSupportedKindInNpmError {
+            media_type,
+            specifier,
+          }
+          .into(),
+        );
+      }
+      self.emitter.emit_parsed_source_sync(
+        &specifier,
+        media_type,
+        // this is probably not super accurate due to require esm, but probably ok.
+        // If we find this causes a lot of churn in the emit cache then we should
+        // investigate how we can make this better
+        ModuleKind::Cjs,
+        &text.into(),
+      )
+    } else {
+      Ok(text)
+    }
+  }
+}
diff --git a/cli/napi/README.md b/cli/napi/README.md
deleted file mode 100644
index 7b359ac6ec..0000000000
--- a/cli/napi/README.md
+++ /dev/null
@@ -1,114 +0,0 @@
-# napi
-
-This directory contains source for Deno's Node-API implementation. It depends on
-`napi_sym` and `deno_napi`.
-
-Files are generally organized the same as in Node.js's implementation to ease in
-ensuring compatibility.
-
-## Adding a new function
-
-Add the symbol name to
-[`cli/napi_sym/symbol_exports.json`](../napi_sym/symbol_exports.json).
-
-```diff
-{
-  "symbols": [
-    ...
-    "napi_get_undefined",
--   "napi_get_null"
-+   "napi_get_null",
-+   "napi_get_boolean"
-  ]
-}
-```
-
-Determine where to place the implementation. `napi_get_boolean` is related to JS
-values so we will place it in `js_native_api.rs`. If something is not clear,
-just create a new file module.
-
-See [`napi_sym`](../napi_sym/) for writing the implementation:
-
-```rust
-#[napi_sym::napi_sym]
-pub fn napi_get_boolean(
-  env: *mut Env,
-  value: bool,
-  result: *mut napi_value,
-) -> Result {
-  // ...
-  Ok(())
-}
-```
-
-Update the generated symbol lists using the script:
-
-```
-deno run --allow-write tools/napi/generate_symbols_lists.js
-```
-
-Add a test in [`/tests/napi`](../../tests/napi/). You can also refer to Node.js
-test suite for Node-API.
-
-```js
-// tests/napi/boolean_test.js
-import { assertEquals, loadTestLibrary } from "./common.js";
-const lib = loadTestLibrary();
-Deno.test("napi get boolean", function () {
-  assertEquals(lib.test_get_boolean(true), true);
-  assertEquals(lib.test_get_boolean(false), false);
-});
-```
-
-```rust
-// tests/napi/src/boolean.rs
-
-use napi_sys::Status::napi_ok;
-use napi_sys::ValueType::napi_boolean;
-use napi_sys::*;
-
-extern "C" fn test_boolean(
-  env: napi_env,
-  info: napi_callback_info,
-) -> napi_value {
-  let (args, argc, _) = crate::get_callback_info!(env, info, 1);
-  assert_eq!(argc, 1);
-
-  let mut ty = -1;
-  assert!(unsafe { napi_typeof(env, args[0], &mut ty) } == napi_ok);
-  assert_eq!(ty, napi_boolean);
-
-  // Use napi_get_boolean here...
-
-  value
-}
-
-pub fn init(env: napi_env, exports: napi_value) {
-  let properties = &[crate::new_property!(env, "test_boolean\0", test_boolean)];
-
-  unsafe {
-    napi_define_properties(env, exports, properties.len(), properties.as_ptr())
-  };
-}
-```
-
-```diff
-// tests/napi/src/lib.rs
-
-+ mod boolean;
-
-...
-
-#[no_mangle]
-unsafe extern "C" fn napi_register_module_v1(
-  env: napi_env,
-  exports: napi_value,
-) -> napi_value {
-  ...
-+ boolean::init(env, exports);
-
-  exports
-}
-```
-
-Run the test using `cargo test -p tests/napi`.
diff --git a/cli/napi/mod.rs b/cli/napi/mod.rs
deleted file mode 100644
index 811efb1ecc..0000000000
--- a/cli/napi/mod.rs
+++ /dev/null
@@ -1,21 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-#![allow(unused_mut)]
-#![allow(non_camel_case_types)]
-#![allow(clippy::undocumented_unsafe_blocks)]
-
-//! Symbols to be exported are now defined in this JSON file.
-//! The `#[napi_sym]` macro checks for missing entries and panics.
-//!
-//! `./tools/napi/generate_symbols_list.js` is used to generate the LINK `cli/exports.def` on Windows,
-//! which is also checked into git.
-//!
-//! To add a new napi function:
-//! 1. Place `#[napi_sym]` on top of your implementation.
-//! 2. Add the function's identifier to this JSON list.
-//! 3. Finally, run `tools/napi/generate_symbols_list.js` to update `cli/napi/generated_symbol_exports_list_*.def`.
-
-pub mod js_native_api;
-pub mod node_api;
-pub mod util;
-pub mod uv;
diff --git a/cli/node.rs b/cli/node.rs
index a3cee8ddee..1d410a726a 100644
--- a/cli/node.rs
+++ b/cli/node.rs
@@ -1,10 +1,14 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use std::borrow::Cow;
 use std::sync::Arc;
 
 use deno_ast::MediaType;
 use deno_ast::ModuleSpecifier;
 use deno_core::error::AnyError;
+use deno_graph::ParsedSourceStore;
+use deno_path_util::url_from_file_path;
+use deno_path_util::url_to_file_path;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::DenoFsNodeResolverEnv;
 use node_resolver::analyze::CjsAnalysis as ExtNodeCjsAnalysis;
@@ -16,8 +20,9 @@ use serde::Serialize;
 
 use crate::cache::CacheDBHash;
 use crate::cache::NodeAnalysisCache;
-use crate::resolver::CliNodeResolver;
-use crate::util::fs::canonicalize_path_maybe_not_exists;
+use crate::cache::ParsedSourceCache;
+use crate::resolver::CjsTracker;
+use crate::util::fs::canonicalize_path_maybe_not_exists_with_fs;
 
 pub type CliNodeCodeTranslator =
   NodeCodeTranslator<CliCjsCodeAnalyzer, DenoFsNodeResolverEnv>;
@@ -30,14 +35,14 @@ pub type CliNodeCodeTranslator =
 /// because the node_modules folder might not exist at that time.
 pub fn resolve_specifier_into_node_modules(
   specifier: &ModuleSpecifier,
+  fs: &dyn deno_fs::FileSystem,
 ) -> ModuleSpecifier {
-  specifier
-    .to_file_path()
+  url_to_file_path(specifier)
     .ok()
     // this path might not exist at the time the graph is being created
     // because the node_modules folder might not yet exist
-    .and_then(|path| canonicalize_path_maybe_not_exists(&path).ok())
-    .and_then(|path| ModuleSpecifier::from_file_path(path).ok())
+    .and_then(|path| canonicalize_path_maybe_not_exists_with_fs(&path, fs).ok())
+    .and_then(|path| url_from_file_path(&path).ok())
     .unwrap_or_else(|| specifier.clone())
 }
 
@@ -54,20 +59,29 @@ pub enum CliCjsAnalysis {
 
 pub struct CliCjsCodeAnalyzer {
   cache: NodeAnalysisCache,
+  cjs_tracker: Arc<CjsTracker>,
   fs: deno_fs::FileSystemRc,
-  node_resolver: Arc<CliNodeResolver>,
+  parsed_source_cache: Option<Arc<ParsedSourceCache>>,
+  // todo(dsherret): hack, remove in https://github.com/denoland/deno/pull/26439
+  // For example, this does not properly handle if cjs analysis was already done
+  // and has been cached.
+  is_npm_main: bool,
 }
 
 impl CliCjsCodeAnalyzer {
   pub fn new(
     cache: NodeAnalysisCache,
+    cjs_tracker: Arc<CjsTracker>,
     fs: deno_fs::FileSystemRc,
-    node_resolver: Arc<CliNodeResolver>,
+    parsed_source_cache: Option<Arc<ParsedSourceCache>>,
+    is_npm_main: bool,
   ) -> Self {
     Self {
       cache,
+      cjs_tracker,
       fs,
-      node_resolver,
+      parsed_source_cache,
+      is_npm_main,
     }
   }
 
@@ -83,7 +97,7 @@ impl CliCjsCodeAnalyzer {
       return Ok(analysis);
     }
 
-    let mut media_type = MediaType::from_specifier(specifier);
+    let media_type = MediaType::from_specifier(specifier);
     if media_type == MediaType::Json {
       return Ok(CliCjsAnalysis::Cjs {
         exports: vec![],
@@ -91,54 +105,53 @@ impl CliCjsCodeAnalyzer {
       });
     }
 
-    if media_type == MediaType::JavaScript {
-      if let Some(package_json) =
-        self.node_resolver.get_closest_package_json(specifier)?
-      {
-        match package_json.typ.as_str() {
-          "commonjs" => {
-            media_type = MediaType::Cjs;
-          }
-          "module" => {
-            media_type = MediaType::Mjs;
-          }
-          _ => {}
-        }
-      }
-    }
+    let cjs_tracker = self.cjs_tracker.clone();
+    let is_npm_main = self.is_npm_main;
+    let is_maybe_cjs =
+      cjs_tracker.is_maybe_cjs(specifier, media_type)? || is_npm_main;
+    let analysis = if is_maybe_cjs {
+      let maybe_parsed_source = self
+        .parsed_source_cache
+        .as_ref()
+        .and_then(|c| c.remove_parsed_source(specifier));
 
-    let analysis = deno_core::unsync::spawn_blocking({
-      let specifier = specifier.clone();
-      let source: Arc<str> = source.into();
-      move || -> Result<_, deno_ast::ParseDiagnostic> {
-        let parsed_source = deno_ast::parse_program(deno_ast::ParseParams {
-          specifier,
-          text: source,
-          media_type,
-          capture_tokens: true,
-          scope_analysis: false,
-          maybe_syntax: None,
-        })?;
-        if parsed_source.is_script() {
-          let analysis = parsed_source.analyze_cjs();
-          Ok(CliCjsAnalysis::Cjs {
-            exports: analysis.exports,
-            reexports: analysis.reexports,
-          })
-        } else if media_type == MediaType::Cjs {
-          // FIXME: `deno_ast` should internally handle MediaType::Cjs implying that
-          // the result must never be Esm
-          Ok(CliCjsAnalysis::Cjs {
-            exports: vec![],
-            reexports: vec![],
-          })
-        } else {
-          Ok(CliCjsAnalysis::Esm)
+      deno_core::unsync::spawn_blocking({
+        let specifier = specifier.clone();
+        let source: Arc<str> = source.into();
+        move || -> Result<_, AnyError> {
+          let parsed_source =
+            maybe_parsed_source.map(Ok).unwrap_or_else(|| {
+              deno_ast::parse_program(deno_ast::ParseParams {
+                specifier,
+                text: source,
+                media_type,
+                capture_tokens: true,
+                scope_analysis: false,
+                maybe_syntax: None,
+              })
+            })?;
+          let is_script = parsed_source.compute_is_script();
+          let is_cjs = cjs_tracker.is_cjs_with_known_is_script(
+            parsed_source.specifier(),
+            media_type,
+            is_script,
+          )? || is_script && is_npm_main;
+          if is_cjs {
+            let analysis = parsed_source.analyze_cjs();
+            Ok(CliCjsAnalysis::Cjs {
+              exports: analysis.exports,
+              reexports: analysis.reexports,
+            })
+          } else {
+            Ok(CliCjsAnalysis::Esm)
+          }
         }
-      }
-    })
-    .await
-    .unwrap()?;
+      })
+      .await
+      .unwrap()?
+    } else {
+      CliCjsAnalysis::Esm
+    };
 
     self
       .cache
@@ -150,11 +163,11 @@ impl CliCjsCodeAnalyzer {
 
 #[async_trait::async_trait(?Send)]
 impl CjsCodeAnalyzer for CliCjsCodeAnalyzer {
-  async fn analyze_cjs(
+  async fn analyze_cjs<'a>(
     &self,
     specifier: &ModuleSpecifier,
-    source: Option<String>,
-  ) -> Result<ExtNodeCjsAnalysis, AnyError> {
+    source: Option<Cow<'a, str>>,
+  ) -> Result<ExtNodeCjsAnalysis<'a>, AnyError> {
     let source = match source {
       Some(source) => source,
       None => {
@@ -162,7 +175,7 @@ impl CjsCodeAnalyzer for CliCjsCodeAnalyzer {
           if let Ok(source_from_file) =
             self.fs.read_text_file_lossy_async(path, None).await
           {
-            source_from_file
+            Cow::Owned(source_from_file)
           } else {
             return Ok(ExtNodeCjsAnalysis::Cjs(CjsAnalysisExports {
               exports: vec![],
diff --git a/cli/npm/byonm.rs b/cli/npm/byonm.rs
index fc095ab16f..4535b07fc5 100644
--- a/cli/npm/byonm.rs
+++ b/cli/npm/byonm.rs
@@ -10,8 +10,8 @@ use deno_core::serde_json;
 use deno_core::url::Url;
 use deno_resolver::npm::ByonmNpmResolver;
 use deno_resolver::npm::ByonmNpmResolverCreateOptions;
+use deno_runtime::deno_node::DenoFsNodeResolverEnv;
 use deno_runtime::deno_node::NodePermissions;
-use deno_runtime::deno_node::NodeRequireResolver;
 use deno_runtime::ops::process::NpmProcessStateProvider;
 use deno_semver::package::PackageReq;
 use node_resolver::NpmResolver;
@@ -25,30 +25,14 @@ use super::InnerCliNpmResolverRef;
 use super::ResolvePkgFolderFromDenoReqError;
 
 pub type CliByonmNpmResolverCreateOptions =
-  ByonmNpmResolverCreateOptions<CliDenoResolverFs>;
-pub type CliByonmNpmResolver = ByonmNpmResolver<CliDenoResolverFs>;
+  ByonmNpmResolverCreateOptions<CliDenoResolverFs, DenoFsNodeResolverEnv>;
+pub type CliByonmNpmResolver =
+  ByonmNpmResolver<CliDenoResolverFs, DenoFsNodeResolverEnv>;
 
 // todo(dsherret): the services hanging off `CliNpmResolver` doesn't seem ideal. We should probably decouple.
 #[derive(Debug)]
 struct CliByonmWrapper(Arc<CliByonmNpmResolver>);
 
-impl NodeRequireResolver for CliByonmWrapper {
-  fn ensure_read_permission<'a>(
-    &self,
-    permissions: &mut dyn NodePermissions,
-    path: &'a Path,
-  ) -> Result<Cow<'a, Path>, AnyError> {
-    if !path
-      .components()
-      .any(|c| c.as_os_str().to_ascii_lowercase() == "node_modules")
-    {
-      permissions.check_read_path(path)
-    } else {
-      Ok(Cow::Borrowed(path))
-    }
-  }
-}
-
 impl NpmProcessStateProvider for CliByonmWrapper {
   fn get_npm_process_state(&self) -> String {
     serde_json::to_string(&NpmProcessState {
@@ -67,10 +51,6 @@ impl CliNpmResolver for CliByonmNpmResolver {
     self
   }
 
-  fn into_require_resolver(self: Arc<Self>) -> Arc<dyn NodeRequireResolver> {
-    Arc::new(CliByonmWrapper(self))
-  }
-
   fn into_process_state_provider(
     self: Arc<Self>,
   ) -> Arc<dyn NpmProcessStateProvider> {
@@ -100,6 +80,21 @@ impl CliNpmResolver for CliByonmNpmResolver {
     .map_err(ResolvePkgFolderFromDenoReqError::Byonm)
   }
 
+  fn ensure_read_permission<'a>(
+    &self,
+    permissions: &mut dyn NodePermissions,
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError> {
+    if !path
+      .components()
+      .any(|c| c.as_os_str().to_ascii_lowercase() == "node_modules")
+    {
+      permissions.check_read_path(path)
+    } else {
+      Ok(Cow::Borrowed(path))
+    }
+  }
+
   fn check_state_hash(&self) -> Option<u64> {
     // it is very difficult to determine the check state hash for byonm
     // so we just return None to signify check caching is not supported
diff --git a/cli/npm/common.rs b/cli/npm/common.rs
index a3a828e745..55f1bc086d 100644
--- a/cli/npm/common.rs
+++ b/cli/npm/common.rs
@@ -3,6 +3,7 @@
 use base64::prelude::BASE64_STANDARD;
 use base64::Engine;
 use deno_core::anyhow::bail;
+use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_npm::npm_rc::RegistryConfig;
 use http::header;
@@ -36,17 +37,21 @@ pub fn maybe_auth_header_for_npm_registry(
   }
 
   if username.is_some() && password.is_some() {
+    // The npm client does some double encoding when generating the
+    // bearer token value, see
+    // https://github.com/npm/cli/blob/780afc50e3a345feb1871a28e33fa48235bc3bd5/workspaces/config/lib/index.js#L846-L851
+    let pw_base64 = BASE64_STANDARD
+      .decode(password.unwrap())
+      .with_context(|| "The password in npmrc is an invalid base64 string")?;
+    let bearer = BASE64_STANDARD.encode(format!(
+      "{}:{}",
+      username.unwrap(),
+      String::from_utf8_lossy(&pw_base64)
+    ));
+
     return Ok(Some((
       header::AUTHORIZATION,
-      header::HeaderValue::from_str(&format!(
-        "Basic {}",
-        BASE64_STANDARD.encode(&format!(
-          "{}:{}",
-          username.unwrap(),
-          password.unwrap()
-        ))
-      ))
-      .unwrap(),
+      header::HeaderValue::from_str(&format!("Basic {}", bearer)).unwrap(),
     )));
   }
 
diff --git a/cli/npm/managed/cache/mod.rs b/cli/npm/managed/cache/mod.rs
index fa0e8c8a59..8ae99f41e0 100644
--- a/cli/npm/managed/cache/mod.rs
+++ b/cli/npm/managed/cache/mod.rs
@@ -26,7 +26,7 @@ use crate::cache::CACHE_PERM;
 use crate::util::fs::atomic_write_file_with_retries;
 use crate::util::fs::hard_link_dir_recursive;
 
-mod registry_info;
+pub mod registry_info;
 mod tarball;
 mod tarball_extract;
 
@@ -36,7 +36,7 @@ pub use tarball::TarballCache;
 /// Stores a single copy of npm packages in a cache.
 #[derive(Debug)]
 pub struct NpmCache {
-  cache_dir: NpmCacheDir,
+  cache_dir: Arc<NpmCacheDir>,
   cache_setting: CacheSetting,
   npmrc: Arc<ResolvedNpmRc>,
   /// ensures a package is only downloaded once per run
@@ -45,7 +45,7 @@ pub struct NpmCache {
 
 impl NpmCache {
   pub fn new(
-    cache_dir: NpmCacheDir,
+    cache_dir: Arc<NpmCacheDir>,
     cache_setting: CacheSetting,
     npmrc: Arc<ResolvedNpmRc>,
   ) -> Self {
@@ -61,6 +61,10 @@ impl NpmCache {
     &self.cache_setting
   }
 
+  pub fn root_dir_path(&self) -> &Path {
+    self.cache_dir.root_dir()
+  }
+
   pub fn root_dir_url(&self) -> &Url {
     self.cache_dir.root_dir_url()
   }
@@ -152,10 +156,6 @@ impl NpmCache {
     self.cache_dir.package_name_folder(name, registry_url)
   }
 
-  pub fn root_folder(&self) -> PathBuf {
-    self.cache_dir.root_dir().to_owned()
-  }
-
   pub fn resolve_package_folder_id_from_specifier(
     &self,
     specifier: &ModuleSpecifier,
diff --git a/cli/npm/managed/cache/registry_info.rs b/cli/npm/managed/cache/registry_info.rs
index 28b19373e9..6d39d3c13f 100644
--- a/cli/npm/managed/cache/registry_info.rs
+++ b/cli/npm/managed/cache/registry_info.rs
@@ -84,7 +84,7 @@ impl RegistryInfoDownloader {
     self.load_package_info_inner(name).await.with_context(|| {
       format!(
         "Error getting response at {} for package \"{}\"",
-        self.get_package_url(name),
+        get_package_url(&self.npmrc, name),
         name
       )
     })
@@ -190,7 +190,7 @@ impl RegistryInfoDownloader {
 
   fn create_load_future(self: &Arc<Self>, name: &str) -> LoadFuture {
     let downloader = self.clone();
-    let package_url = self.get_package_url(name);
+    let package_url = get_package_url(&self.npmrc, name);
     let registry_config = self.npmrc.get_registry_config(name);
     let maybe_auth_header =
       match maybe_auth_header_for_npm_registry(registry_config) {
@@ -202,10 +202,13 @@ impl RegistryInfoDownloader {
     let guard = self.progress_bar.update(package_url.as_str());
     let name = name.to_string();
     async move {
-      let maybe_bytes = downloader
-        .http_client_provider
-        .get_or_create()?
-        .download_with_progress(package_url, maybe_auth_header, &guard)
+      let client = downloader.http_client_provider.get_or_create()?;
+      let maybe_bytes = client
+        .download_with_progress_and_retries(
+          package_url,
+          maybe_auth_header,
+          &guard,
+        )
         .await?;
       match maybe_bytes {
         Some(bytes) => {
@@ -236,25 +239,36 @@ impl RegistryInfoDownloader {
     .map(|r| r.map_err(Arc::new))
     .boxed_local()
   }
-
-  fn get_package_url(&self, name: &str) -> Url {
-    let registry_url = self.npmrc.get_registry_url(name);
-    // list of all characters used in npm packages:
-    //  !, ', (, ), *, -, ., /, [0-9], @, [A-Za-z], _, ~
-    const ASCII_SET: percent_encoding::AsciiSet =
-      percent_encoding::NON_ALPHANUMERIC
-        .remove(b'!')
-        .remove(b'\'')
-        .remove(b'(')
-        .remove(b')')
-        .remove(b'*')
-        .remove(b'-')
-        .remove(b'.')
-        .remove(b'/')
-        .remove(b'@')
-        .remove(b'_')
-        .remove(b'~');
-    let name = percent_encoding::utf8_percent_encode(name, &ASCII_SET);
-    registry_url.join(&name.to_string()).unwrap()
-  }
+}
+
+pub fn get_package_url(npmrc: &ResolvedNpmRc, name: &str) -> Url {
+  let registry_url = npmrc.get_registry_url(name);
+  // The '/' character in scoped package names "@scope/name" must be
+  // encoded for older third party registries. Newer registries and
+  // npm itself support both ways
+  //   - encoded: https://registry.npmjs.org/@rollup%2fplugin-json
+  //   - non-ecoded: https://registry.npmjs.org/@rollup/plugin-json
+  // To support as many third party registries as possible we'll
+  // always encode the '/' character.
+
+  // list of all characters used in npm packages:
+  //  !, ', (, ), *, -, ., /, [0-9], @, [A-Za-z], _, ~
+  const ASCII_SET: percent_encoding::AsciiSet =
+    percent_encoding::NON_ALPHANUMERIC
+      .remove(b'!')
+      .remove(b'\'')
+      .remove(b'(')
+      .remove(b')')
+      .remove(b'*')
+      .remove(b'-')
+      .remove(b'.')
+      .remove(b'@')
+      .remove(b'_')
+      .remove(b'~');
+  let name = percent_encoding::utf8_percent_encode(name, &ASCII_SET);
+  registry_url
+    // Ensure that scoped package name percent encoding is lower cased
+    // to match npm.
+    .join(&name.to_string().replace("%2F", "%2f"))
+    .unwrap()
 }
diff --git a/cli/npm/managed/cache/tarball.rs b/cli/npm/managed/cache/tarball.rs
index 4bcee38ea8..7cf88d6d64 100644
--- a/cli/npm/managed/cache/tarball.rs
+++ b/cli/npm/managed/cache/tarball.rs
@@ -172,7 +172,7 @@ impl TarballCache {
       let guard = tarball_cache.progress_bar.update(&dist.tarball);
       let result = tarball_cache.http_client_provider
         .get_or_create()?
-        .download_with_progress(tarball_uri, maybe_auth_header, &guard)
+        .download_with_progress_and_retries(tarball_uri, maybe_auth_header, &guard)
         .await;
       let maybe_bytes = match result {
         Ok(maybe_bytes) => maybe_bytes,
diff --git a/cli/npm/managed/mod.rs b/cli/npm/managed/mod.rs
index ec50a9c65a..4a91bc3474 100644
--- a/cli/npm/managed/mod.rs
+++ b/cli/npm/managed/mod.rs
@@ -12,6 +12,7 @@ use deno_cache_dir::npm::NpmCacheDir;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_core::serde_json;
+use deno_core::url::Url;
 use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_npm::registry::NpmPackageInfo;
 use deno_npm::registry::NpmRegistryApi;
@@ -24,12 +25,12 @@ use deno_npm::NpmSystemInfo;
 use deno_runtime::colors;
 use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::NodePermissions;
-use deno_runtime::deno_node::NodeRequireResolver;
 use deno_runtime::ops::process::NpmProcessStateProvider;
 use deno_semver::package::PackageNv;
 use deno_semver::package::PackageReq;
 use node_resolver::errors::PackageFolderResolveError;
 use node_resolver::errors::PackageFolderResolveIoError;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NpmResolver;
 use resolution::AddPkgReqsResult;
 
@@ -38,7 +39,7 @@ use crate::args::LifecycleScriptsConfig;
 use crate::args::NpmInstallDepsProvider;
 use crate::args::NpmProcessState;
 use crate::args::NpmProcessStateKind;
-use crate::cache::DenoCacheEnvFsAdapter;
+use crate::args::PackageJsonDepValueParseWithLocationError;
 use crate::cache::FastInsecureHasher;
 use crate::http_util::HttpClientProvider;
 use crate::util::fs::canonicalize_path_maybe_not_exists_with_fs;
@@ -55,7 +56,7 @@ use super::CliNpmResolver;
 use super::InnerCliNpmResolverRef;
 use super::ResolvePkgFolderFromDenoReqError;
 
-mod cache;
+pub mod cache;
 mod registry;
 mod resolution;
 mod resolvers;
@@ -65,12 +66,12 @@ pub enum CliNpmResolverManagedSnapshotOption {
   Specified(Option<ValidSerializedNpmResolutionSnapshot>),
 }
 
-pub struct CliNpmResolverManagedCreateOptions {
+pub struct CliManagedNpmResolverCreateOptions {
   pub snapshot: CliNpmResolverManagedSnapshotOption,
   pub maybe_lockfile: Option<Arc<CliLockfile>>,
   pub fs: Arc<dyn deno_runtime::deno_fs::FileSystem>,
   pub http_client_provider: Arc<crate::http_util::HttpClientProvider>,
-  pub npm_global_cache_dir: PathBuf,
+  pub npm_cache_dir: Arc<NpmCacheDir>,
   pub cache_setting: crate::args::CacheSetting,
   pub text_only_progress_bar: crate::util::progress_bar::ProgressBar,
   pub maybe_node_modules_path: Option<PathBuf>,
@@ -81,7 +82,7 @@ pub struct CliNpmResolverManagedCreateOptions {
 }
 
 pub async fn create_managed_npm_resolver_for_lsp(
-  options: CliNpmResolverManagedCreateOptions,
+  options: CliManagedNpmResolverCreateOptions,
 ) -> Arc<dyn CliNpmResolver> {
   let npm_cache = create_cache(&options);
   let npm_api = create_api(&options, npm_cache.clone());
@@ -114,7 +115,7 @@ pub async fn create_managed_npm_resolver_for_lsp(
 }
 
 pub async fn create_managed_npm_resolver(
-  options: CliNpmResolverManagedCreateOptions,
+  options: CliManagedNpmResolverCreateOptions,
 ) -> Result<Arc<dyn CliNpmResolver>, AnyError> {
   let npm_cache = create_cache(&options);
   let npm_api = create_api(&options, npm_cache.clone());
@@ -188,20 +189,16 @@ fn create_inner(
   ))
 }
 
-fn create_cache(options: &CliNpmResolverManagedCreateOptions) -> Arc<NpmCache> {
+fn create_cache(options: &CliManagedNpmResolverCreateOptions) -> Arc<NpmCache> {
   Arc::new(NpmCache::new(
-    NpmCacheDir::new(
-      &DenoCacheEnvFsAdapter(options.fs.as_ref()),
-      options.npm_global_cache_dir.clone(),
-      options.npmrc.get_all_known_registries_urls(),
-    ),
+    options.npm_cache_dir.clone(),
     options.cache_setting.clone(),
     options.npmrc.clone(),
   ))
 }
 
 fn create_api(
-  options: &CliNpmResolverManagedCreateOptions,
+  options: &CliManagedNpmResolverCreateOptions,
   npm_cache: Arc<NpmCache>,
 ) -> Arc<CliNpmRegistryApi> {
   Arc::new(CliNpmRegistryApi::new(
@@ -258,6 +255,35 @@ async fn snapshot_from_lockfile(
   Ok(snapshot)
 }
 
+#[derive(Debug)]
+struct ManagedInNpmPackageChecker {
+  root_dir: Url,
+}
+
+impl InNpmPackageChecker for ManagedInNpmPackageChecker {
+  fn in_npm_package(&self, specifier: &Url) -> bool {
+    specifier.as_ref().starts_with(self.root_dir.as_str())
+  }
+}
+
+pub struct CliManagedInNpmPkgCheckerCreateOptions<'a> {
+  pub root_cache_dir_url: &'a Url,
+  pub maybe_node_modules_path: Option<&'a Path>,
+}
+
+pub fn create_managed_in_npm_pkg_checker(
+  options: CliManagedInNpmPkgCheckerCreateOptions,
+) -> Arc<dyn InNpmPackageChecker> {
+  let root_dir = match options.maybe_node_modules_path {
+    Some(node_modules_folder) => {
+      deno_path_util::url_from_directory_path(node_modules_folder).unwrap()
+    }
+    None => options.root_cache_dir_url.clone(),
+  };
+  debug_assert!(root_dir.as_str().ends_with('/'));
+  Arc::new(ManagedInNpmPackageChecker { root_dir })
+}
+
 /// An npm resolver where the resolution is managed by Deno rather than
 /// the user bringing their own node_modules (BYONM) on the file system.
 pub struct ManagedCliNpmResolver {
@@ -480,19 +506,24 @@ impl ManagedCliNpmResolver {
     self.resolution.resolve_pkg_id_from_pkg_req(req)
   }
 
-  pub fn ensure_no_pkg_json_dep_errors(&self) -> Result<(), AnyError> {
+  pub fn ensure_no_pkg_json_dep_errors(
+    &self,
+  ) -> Result<(), Box<PackageJsonDepValueParseWithLocationError>> {
     for err in self.npm_install_deps_provider.pkg_json_dep_errors() {
-      match err {
+      match &err.source {
         deno_package_json::PackageJsonDepValueParseError::VersionReq(_) => {
-          return Err(
-            AnyError::from(err.clone())
-              .context("Failed to install from package.json"),
-          );
+          return Err(Box::new(err.clone()));
         }
         deno_package_json::PackageJsonDepValueParseError::Unsupported {
           ..
         } => {
-          log::warn!("{} {} in package.json", colors::yellow("Warning"), err)
+          // only warn for this one
+          log::warn!(
+            "{} {}\n    at {}",
+            colors::yellow("Warning"),
+            err.source,
+            err.location,
+          )
         }
       }
     }
@@ -549,8 +580,16 @@ impl ManagedCliNpmResolver {
       .map_err(|err| err.into())
   }
 
-  pub fn global_cache_root_folder(&self) -> PathBuf {
-    self.npm_cache.root_folder()
+  pub fn maybe_node_modules_path(&self) -> Option<&Path> {
+    self.fs_resolver.node_modules_path()
+  }
+
+  pub fn global_cache_root_path(&self) -> &Path {
+    self.npm_cache.root_dir_path()
+  }
+
+  pub fn global_cache_root_url(&self) -> &Url {
+    self.npm_cache.root_dir_url()
   }
 }
 
@@ -585,22 +624,6 @@ impl NpmResolver for ManagedCliNpmResolver {
     log::debug!("Resolved {} from {} to {}", name, referrer, path.display());
     Ok(path)
   }
-
-  fn in_npm_package(&self, specifier: &ModuleSpecifier) -> bool {
-    let root_dir_url = self.fs_resolver.root_dir_url();
-    debug_assert!(root_dir_url.as_str().ends_with('/'));
-    specifier.as_ref().starts_with(root_dir_url.as_str())
-  }
-}
-
-impl NodeRequireResolver for ManagedCliNpmResolver {
-  fn ensure_read_permission<'a>(
-    &self,
-    permissions: &mut dyn NodePermissions,
-    path: &'a Path,
-  ) -> Result<Cow<'a, Path>, AnyError> {
-    self.fs_resolver.ensure_read_permission(permissions, path)
-  }
 }
 
 impl NpmProcessStateProvider for ManagedCliNpmResolver {
@@ -617,10 +640,6 @@ impl CliNpmResolver for ManagedCliNpmResolver {
     self
   }
 
-  fn into_require_resolver(self: Arc<Self>) -> Arc<dyn NodeRequireResolver> {
-    self
-  }
-
   fn into_process_state_provider(
     self: Arc<Self>,
   ) -> Arc<dyn NpmProcessStateProvider> {
@@ -681,6 +700,14 @@ impl CliNpmResolver for ManagedCliNpmResolver {
       .map_err(ResolvePkgFolderFromDenoReqError::Managed)
   }
 
+  fn ensure_read_permission<'a>(
+    &self,
+    permissions: &mut dyn NodePermissions,
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError> {
+    self.fs_resolver.ensure_read_permission(permissions, path)
+  }
+
   fn check_state_hash(&self) -> Option<u64> {
     // We could go further and check all the individual
     // npm packages, but that's probably overkill.
diff --git a/cli/npm/managed/resolvers/common.rs b/cli/npm/managed/resolvers/common.rs
index 867bb4168a..590f8fb25c 100644
--- a/cli/npm/managed/resolvers/common.rs
+++ b/cli/npm/managed/resolvers/common.rs
@@ -17,7 +17,6 @@ use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_core::futures;
 use deno_core::futures::StreamExt;
-use deno_core::url::Url;
 use deno_npm::NpmPackageCacheFolderId;
 use deno_npm::NpmPackageId;
 use deno_npm::NpmResolutionPackage;
@@ -30,9 +29,6 @@ use crate::npm::managed::cache::TarballCache;
 /// Part of the resolution that interacts with the file system.
 #[async_trait(?Send)]
 pub trait NpmPackageFsResolver: Send + Sync {
-  /// Specifier for the root directory.
-  fn root_dir_url(&self) -> &Url;
-
   /// The local node_modules folder if it is applicable to the implementation.
   fn node_modules_path(&self) -> Option<&Path>;
 
diff --git a/cli/npm/managed/resolvers/common/lifecycle_scripts.rs b/cli/npm/managed/resolvers/common/lifecycle_scripts.rs
index b358c35856..5735f52482 100644
--- a/cli/npm/managed/resolvers/common/lifecycle_scripts.rs
+++ b/cli/npm/managed/resolvers/common/lifecycle_scripts.rs
@@ -2,6 +2,8 @@
 
 use super::bin_entries::BinEntries;
 use crate::args::LifecycleScriptsConfig;
+use crate::task_runner::TaskStdio;
+use crate::util::progress_bar::ProgressBar;
 use deno_core::anyhow::Context;
 use deno_npm::resolution::NpmResolutionSnapshot;
 use deno_runtime::deno_io::FromRawIoHandle;
@@ -148,6 +150,7 @@ impl<'a> LifecycleScripts<'a> {
     snapshot: &NpmResolutionSnapshot,
     packages: &[NpmResolutionPackage],
     root_node_modules_dir_path: Option<&Path>,
+    progress_bar: &ProgressBar,
   ) -> Result<(), AnyError> {
     self.warn_not_run_scripts()?;
     let get_package_path =
@@ -201,7 +204,15 @@ impl<'a> LifecycleScripts<'a> {
             {
               continue;
             }
-            let exit_code = crate::task_runner::run_task(
+            let _guard = progress_bar.update_with_prompt(
+              crate::util::progress_bar::ProgressMessagePrompt::Initialize,
+              &format!("{}: running '{script_name}' script", package.id.nv),
+            );
+            let crate::task_runner::TaskResult {
+              exit_code,
+              stderr,
+              stdout,
+            } = crate::task_runner::run_task(
               crate::task_runner::RunTaskOptions {
                 task_name: script_name,
                 script,
@@ -211,15 +222,37 @@ impl<'a> LifecycleScripts<'a> {
                 init_cwd,
                 argv: &[],
                 root_node_modules_dir: root_node_modules_dir_path,
+                stdio: Some(crate::task_runner::TaskIo {
+                  stderr: TaskStdio::piped(),
+                  stdout: TaskStdio::piped(),
+                }),
               },
             )
             .await?;
+            let stdout = stdout.unwrap();
+            let stderr = stderr.unwrap();
             if exit_code != 0 {
               log::warn!(
-                "error: script '{}' in '{}' failed with exit code {}",
+                "error: script '{}' in '{}' failed with exit code {}{}{}",
                 script_name,
                 package.id.nv,
                 exit_code,
+                if !stdout.trim_ascii().is_empty() {
+                  format!(
+                    "\nstdout:\n{}\n",
+                    String::from_utf8_lossy(&stdout).trim()
+                  )
+                } else {
+                  String::new()
+                },
+                if !stderr.trim_ascii().is_empty() {
+                  format!(
+                    "\nstderr:\n{}\n",
+                    String::from_utf8_lossy(&stderr).trim()
+                  )
+                } else {
+                  String::new()
+                },
               );
               failed_packages.push(&package.id.nv);
               // assume if earlier script fails, later ones will fail too
diff --git a/cli/npm/managed/resolvers/global.rs b/cli/npm/managed/resolvers/global.rs
index 5be315e992..f0193e78e9 100644
--- a/cli/npm/managed/resolvers/global.rs
+++ b/cli/npm/managed/resolvers/global.rs
@@ -11,7 +11,6 @@ use crate::colors;
 use async_trait::async_trait;
 use deno_ast::ModuleSpecifier;
 use deno_core::error::AnyError;
-use deno_core::url::Url;
 use deno_npm::NpmPackageCacheFolderId;
 use deno_npm::NpmPackageId;
 use deno_npm::NpmResolutionPackage;
@@ -56,7 +55,7 @@ impl GlobalNpmPackageResolver {
     Self {
       registry_read_permission_checker: RegistryReadPermissionChecker::new(
         fs,
-        cache.root_folder(),
+        cache.root_dir_path().to_path_buf(),
       ),
       cache,
       tarball_cache,
@@ -69,10 +68,6 @@ impl GlobalNpmPackageResolver {
 
 #[async_trait(?Send)]
 impl NpmPackageFsResolver for GlobalNpmPackageResolver {
-  fn root_dir_url(&self) -> &Url {
-    self.cache.root_dir_url()
-  }
-
   fn node_modules_path(&self) -> Option<&Path> {
     None
   }
diff --git a/cli/npm/managed/resolvers/local.rs b/cli/npm/managed/resolvers/local.rs
index 63a972a431..0968be8a7e 100644
--- a/cli/npm/managed/resolvers/local.rs
+++ b/cli/npm/managed/resolvers/local.rs
@@ -155,10 +155,6 @@ impl LocalNpmPackageResolver {
 
 #[async_trait(?Send)]
 impl NpmPackageFsResolver for LocalNpmPackageResolver {
-  fn root_dir_url(&self) -> &Url {
-    &self.root_node_modules_url
-  }
-
   fn node_modules_path(&self) -> Option<&Path> {
     Some(self.root_node_modules_path.as_ref())
   }
@@ -713,6 +709,7 @@ async fn sync_resolution_with_fs(
       snapshot,
       &package_partitions.packages,
       Some(root_node_modules_dir_path),
+      progress_bar,
     )
     .await?;
 
diff --git a/cli/npm/mod.rs b/cli/npm/mod.rs
index 53baaf77b4..0d434ca27f 100644
--- a/cli/npm/mod.rs
+++ b/cli/npm/mod.rs
@@ -4,30 +4,37 @@ mod byonm;
 mod common;
 mod managed;
 
+use std::borrow::Cow;
 use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
 
+use common::maybe_auth_header_for_npm_registry;
 use dashmap::DashMap;
 use deno_ast::ModuleSpecifier;
 use deno_core::error::AnyError;
 use deno_core::serde_json;
+use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_npm::registry::NpmPackageInfo;
+use deno_resolver::npm::ByonmInNpmPackageChecker;
 use deno_resolver::npm::ByonmNpmResolver;
 use deno_resolver::npm::ByonmResolvePkgFolderFromDenoReqError;
-use deno_runtime::deno_node::NodeRequireResolver;
+use deno_runtime::deno_node::NodePermissions;
 use deno_runtime::ops::process::NpmProcessStateProvider;
 use deno_semver::package::PackageNv;
 use deno_semver::package::PackageReq;
+use managed::cache::registry_info::get_package_url;
+use managed::create_managed_in_npm_pkg_checker;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NpmResolver;
 use thiserror::Error;
 
-use crate::args::npm_registry_url;
 use crate::file_fetcher::FileFetcher;
 
 pub use self::byonm::CliByonmNpmResolver;
 pub use self::byonm::CliByonmNpmResolverCreateOptions;
-pub use self::managed::CliNpmResolverManagedCreateOptions;
+pub use self::managed::CliManagedInNpmPkgCheckerCreateOptions;
+pub use self::managed::CliManagedNpmResolverCreateOptions;
 pub use self::managed::CliNpmResolverManagedSnapshotOption;
 pub use self::managed::ManagedCliNpmResolver;
 
@@ -40,7 +47,7 @@ pub enum ResolvePkgFolderFromDenoReqError {
 }
 
 pub enum CliNpmResolverCreateOptions {
-  Managed(CliNpmResolverManagedCreateOptions),
+  Managed(CliManagedNpmResolverCreateOptions),
   Byonm(CliByonmNpmResolverCreateOptions),
 }
 
@@ -66,6 +73,22 @@ pub async fn create_cli_npm_resolver(
   }
 }
 
+pub enum CreateInNpmPkgCheckerOptions<'a> {
+  Managed(CliManagedInNpmPkgCheckerCreateOptions<'a>),
+  Byonm,
+}
+
+pub fn create_in_npm_pkg_checker(
+  options: CreateInNpmPkgCheckerOptions,
+) -> Arc<dyn InNpmPackageChecker> {
+  match options {
+    CreateInNpmPkgCheckerOptions::Managed(options) => {
+      create_managed_in_npm_pkg_checker(options)
+    }
+    CreateInNpmPkgCheckerOptions::Byonm => Arc::new(ByonmInNpmPackageChecker),
+  }
+}
+
 pub enum InnerCliNpmResolverRef<'a> {
   Managed(&'a ManagedCliNpmResolver),
   #[allow(dead_code)]
@@ -74,7 +97,6 @@ pub enum InnerCliNpmResolverRef<'a> {
 
 pub trait CliNpmResolver: NpmResolver {
   fn into_npm_resolver(self: Arc<Self>) -> Arc<dyn NpmResolver>;
-  fn into_require_resolver(self: Arc<Self>) -> Arc<dyn NodeRequireResolver>;
   fn into_process_state_provider(
     self: Arc<Self>,
   ) -> Arc<dyn NpmProcessStateProvider>;
@@ -105,6 +127,12 @@ pub trait CliNpmResolver: NpmResolver {
     referrer: &ModuleSpecifier,
   ) -> Result<PathBuf, ResolvePkgFolderFromDenoReqError>;
 
+  fn ensure_read_permission<'a>(
+    &self,
+    permissions: &mut dyn NodePermissions,
+    path: &'a Path,
+  ) -> Result<Cow<'a, Path>, AnyError>;
+
   /// Returns a hash returning the state of the npm resolver
   /// or `None` if the state currently can't be determined.
   fn check_state_hash(&self) -> Option<u64>;
@@ -115,14 +143,19 @@ pub struct NpmFetchResolver {
   nv_by_req: DashMap<PackageReq, Option<PackageNv>>,
   info_by_name: DashMap<String, Option<Arc<NpmPackageInfo>>>,
   file_fetcher: Arc<FileFetcher>,
+  npmrc: Arc<ResolvedNpmRc>,
 }
 
 impl NpmFetchResolver {
-  pub fn new(file_fetcher: Arc<FileFetcher>) -> Self {
+  pub fn new(
+    file_fetcher: Arc<FileFetcher>,
+    npmrc: Arc<ResolvedNpmRc>,
+  ) -> Self {
     Self {
       nv_by_req: Default::default(),
       info_by_name: Default::default(),
       file_fetcher,
+      npmrc,
     }
   }
 
@@ -157,11 +190,21 @@ impl NpmFetchResolver {
       return info.value().clone();
     }
     let fetch_package_info = || async {
-      let info_url = npm_registry_url().join(name).ok()?;
+      let info_url = get_package_url(&self.npmrc, name);
       let file_fetcher = self.file_fetcher.clone();
+      let registry_config = self.npmrc.get_registry_config(name);
+      // TODO(bartlomieju): this should error out, not use `.ok()`.
+      let maybe_auth_header =
+        maybe_auth_header_for_npm_registry(registry_config).ok()?;
       // spawn due to the lsp's `Send` requirement
       let file = deno_core::unsync::spawn(async move {
-        file_fetcher.fetch_bypass_permissions(&info_url).await.ok()
+        file_fetcher
+          .fetch_bypass_permissions_with_maybe_auth(
+            &info_url,
+            maybe_auth_header,
+          )
+          .await
+          .ok()
       })
       .await
       .ok()??;
@@ -172,3 +215,15 @@ impl NpmFetchResolver {
     info
   }
 }
+
+pub const NPM_CONFIG_USER_AGENT_ENV_VAR: &str = "npm_config_user_agent";
+
+pub fn get_npm_config_user_agent() -> String {
+  format!(
+    "deno/{} npm/? deno/{} {} {}",
+    env!("CARGO_PKG_VERSION"),
+    env!("CARGO_PKG_VERSION"),
+    std::env::consts::OS,
+    std::env::consts::ARCH
+  )
+}
diff --git a/cli/resolver.rs b/cli/resolver.rs
index 7804261b8b..710b975093 100644
--- a/cli/resolver.rs
+++ b/cli/resolver.rs
@@ -4,6 +4,7 @@ use async_trait::async_trait;
 use dashmap::DashMap;
 use dashmap::DashSet;
 use deno_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_config::workspace::MappedResolution;
 use deno_config::workspace::MappedResolutionDiagnostic;
 use deno_config::workspace::MappedResolutionError;
@@ -11,6 +12,7 @@ use deno_config::workspace::WorkspaceResolver;
 use deno_core::anyhow::anyhow;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
+use deno_core::url::Url;
 use deno_core::ModuleSourceCode;
 use deno_core::ModuleSpecifier;
 use deno_graph::source::ResolutionMode;
@@ -29,6 +31,7 @@ use deno_runtime::deno_fs;
 use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::is_builtin_node_module;
 use deno_runtime::deno_node::NodeResolver;
+use deno_runtime::deno_node::PackageJsonResolver;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_semver::package::PackageReq;
 use node_resolver::errors::ClosestPkgJsonError;
@@ -38,15 +41,16 @@ use node_resolver::errors::PackageFolderResolveErrorKind;
 use node_resolver::errors::PackageFolderResolveIoError;
 use node_resolver::errors::PackageNotFoundError;
 use node_resolver::errors::PackageResolveErrorKind;
-use node_resolver::errors::UrlToNodeResolutionError;
+use node_resolver::errors::PackageSubpathResolveError;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NodeModuleKind;
 use node_resolver::NodeResolution;
 use node_resolver::NodeResolutionMode;
-use node_resolver::PackageJson;
 use std::borrow::Cow;
 use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
+use thiserror::Error;
 
 use crate::args::JsxImportSourceConfig;
 use crate::args::DENO_DISABLE_PEDANTIC_NODE_WARNINGS;
@@ -54,6 +58,7 @@ use crate::node::CliNodeCodeTranslator;
 use crate::npm::CliNpmResolver;
 use crate::npm::InnerCliNpmResolverRef;
 use crate::util::sync::AtomicFlag;
+use crate::util::text_encoding::from_utf8_lossy_owned;
 
 pub struct ModuleCodeStringSource {
   pub code: ModuleSourceCode,
@@ -103,36 +108,32 @@ impl deno_resolver::fs::DenoResolverFs for CliDenoResolverFs {
 
 #[derive(Debug)]
 pub struct CliNodeResolver {
-  cjs_resolutions: Arc<CjsResolutionStore>,
+  cjs_tracker: Arc<CjsTracker>,
   fs: Arc<dyn deno_fs::FileSystem>,
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
   node_resolver: Arc<NodeResolver>,
   npm_resolver: Arc<dyn CliNpmResolver>,
 }
 
 impl CliNodeResolver {
   pub fn new(
-    cjs_resolutions: Arc<CjsResolutionStore>,
+    cjs_tracker: Arc<CjsTracker>,
     fs: Arc<dyn deno_fs::FileSystem>,
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
     node_resolver: Arc<NodeResolver>,
     npm_resolver: Arc<dyn CliNpmResolver>,
   ) -> Self {
     Self {
-      cjs_resolutions,
+      cjs_tracker,
       fs,
+      in_npm_pkg_checker,
       node_resolver,
       npm_resolver,
     }
   }
 
   pub fn in_npm_package(&self, specifier: &ModuleSpecifier) -> bool {
-    self.npm_resolver.in_npm_package(specifier)
-  }
-
-  pub fn get_closest_package_json(
-    &self,
-    referrer: &ModuleSpecifier,
-  ) -> Result<Option<Arc<PackageJson>>, ClosestPkgJsonError> {
-    self.node_resolver.get_closest_package_json(referrer)
+    self.in_npm_pkg_checker.in_npm_package(specifier)
   }
 
   pub fn resolve_if_for_npm_pkg(
@@ -152,8 +153,7 @@ impl CliNodeResolver {
           | NodeResolveErrorKind::UnsupportedEsmUrlScheme(_)
           | NodeResolveErrorKind::DataUrlReferrer(_)
           | NodeResolveErrorKind::TypesNotFound(_)
-          | NodeResolveErrorKind::FinalizeResolution(_)
-          | NodeResolveErrorKind::UrlToNodeResolution(_) => Err(err.into()),
+          | NodeResolveErrorKind::FinalizeResolution(_) => Err(err.into()),
           NodeResolveErrorKind::PackageResolve(err) => {
             let err = err.into_kind();
             match err {
@@ -215,7 +215,11 @@ impl CliNodeResolver {
     referrer: &ModuleSpecifier,
     mode: NodeResolutionMode,
   ) -> Result<NodeResolution, NodeResolveError> {
-    let referrer_kind = if self.cjs_resolutions.contains(referrer) {
+    let referrer_kind = if self
+      .cjs_tracker
+      .is_maybe_cjs(referrer, MediaType::from_specifier(referrer))
+      .map_err(|err| NodeResolveErrorKind::PackageResolve(err.into()))?
+    {
       NodeModuleKind::Cjs
     } else {
       NodeModuleKind::Esm
@@ -225,7 +229,7 @@ impl CliNodeResolver {
       self
         .node_resolver
         .resolve(specifier, referrer, referrer_kind, mode)?;
-    Ok(self.handle_node_resolution(res))
+    Ok(res)
   }
 
   pub fn resolve_req_reference(
@@ -233,7 +237,7 @@ impl CliNodeResolver {
     req_ref: &NpmPackageReqReference,
     referrer: &ModuleSpecifier,
     mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, AnyError> {
+  ) -> Result<ModuleSpecifier, AnyError> {
     self.resolve_req_with_sub_path(
       req_ref.req(),
       req_ref.sub_path(),
@@ -248,7 +252,7 @@ impl CliNodeResolver {
     sub_path: Option<&str>,
     referrer: &ModuleSpecifier,
     mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, AnyError> {
+  ) -> Result<ModuleSpecifier, AnyError> {
     let package_folder = self
       .npm_resolver
       .resolve_pkg_folder_from_deno_module_req(req, referrer)?;
@@ -259,7 +263,7 @@ impl CliNodeResolver {
       mode,
     );
     match resolution_result {
-      Ok(resolution) => Ok(resolution),
+      Ok(url) => Ok(url),
       Err(err) => {
         if self.npm_resolver.as_byonm().is_some() {
           let package_json_path = package_folder.join("package.json");
@@ -270,7 +274,7 @@ impl CliNodeResolver {
             ));
           }
         }
-        Err(err)
+        Err(err.into())
       }
     }
   }
@@ -281,16 +285,13 @@ impl CliNodeResolver {
     sub_path: Option<&str>,
     maybe_referrer: Option<&ModuleSpecifier>,
     mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, AnyError> {
-    let res = self
-      .node_resolver
-      .resolve_package_subpath_from_deno_module(
-        package_folder,
-        sub_path,
-        maybe_referrer,
-        mode,
-      )?;
-    Ok(self.handle_node_resolution(res))
+  ) -> Result<ModuleSpecifier, PackageSubpathResolveError> {
+    self.node_resolver.resolve_package_subpath_from_deno_module(
+      package_folder,
+      sub_path,
+      maybe_referrer,
+      mode,
+    )
   }
 
   pub fn handle_if_in_node_modules(
@@ -305,74 +306,42 @@ impl CliNodeResolver {
       // so canoncalize then check if it's in the node_modules directory.
       // If so, check if we need to store this specifier as being a CJS
       // resolution.
-      let specifier =
-        crate::node::resolve_specifier_into_node_modules(specifier);
-      if self.in_npm_package(&specifier) {
-        let resolution =
-          self.node_resolver.url_to_node_resolution(specifier)?;
-        if let NodeResolution::CommonJs(specifier) = &resolution {
-          self.cjs_resolutions.insert(specifier.clone());
-        }
-        return Ok(Some(resolution.into_url()));
-      }
+      let specifier = crate::node::resolve_specifier_into_node_modules(
+        specifier,
+        self.fs.as_ref(),
+      );
+      return Ok(Some(specifier));
     }
 
     Ok(None)
   }
-
-  pub fn url_to_node_resolution(
-    &self,
-    specifier: ModuleSpecifier,
-  ) -> Result<NodeResolution, UrlToNodeResolutionError> {
-    self.node_resolver.url_to_node_resolution(specifier)
-  }
-
-  fn handle_node_resolution(
-    &self,
-    resolution: NodeResolution,
-  ) -> NodeResolution {
-    if let NodeResolution::CommonJs(specifier) = &resolution {
-      // remember that this was a common js resolution
-      self.cjs_resolutions.insert(specifier.clone());
-    }
-    resolution
-  }
 }
 
+#[derive(Debug, Error)]
+#[error("{media_type} files are not supported in npm packages: {specifier}")]
+pub struct NotSupportedKindInNpmError {
+  pub media_type: MediaType,
+  pub specifier: Url,
+}
+
+// todo(dsherret): move to module_loader.rs (it seems to be here due to use in standalone)
 #[derive(Clone)]
 pub struct NpmModuleLoader {
-  cjs_resolutions: Arc<CjsResolutionStore>,
-  node_code_translator: Arc<CliNodeCodeTranslator>,
+  cjs_tracker: Arc<CjsTracker>,
   fs: Arc<dyn deno_fs::FileSystem>,
-  node_resolver: Arc<CliNodeResolver>,
+  node_code_translator: Arc<CliNodeCodeTranslator>,
 }
 
 impl NpmModuleLoader {
   pub fn new(
-    cjs_resolutions: Arc<CjsResolutionStore>,
-    node_code_translator: Arc<CliNodeCodeTranslator>,
+    cjs_tracker: Arc<CjsTracker>,
     fs: Arc<dyn deno_fs::FileSystem>,
-    node_resolver: Arc<CliNodeResolver>,
+    node_code_translator: Arc<CliNodeCodeTranslator>,
   ) -> Self {
     Self {
-      cjs_resolutions,
+      cjs_tracker,
       node_code_translator,
       fs,
-      node_resolver,
-    }
-  }
-
-  pub async fn load_if_in_npm_package(
-    &self,
-    specifier: &ModuleSpecifier,
-    maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Option<Result<ModuleCodeStringSource, AnyError>> {
-    if self.node_resolver.in_npm_package(specifier)
-      || (specifier.scheme() == "file" && specifier.path().ends_with(".cjs"))
-    {
-      Some(self.load(specifier, maybe_referrer).await)
-    } else {
-      None
     }
   }
 
@@ -418,27 +387,30 @@ impl NpmModuleLoader {
         }
       })?;
 
-    let code = if self.cjs_resolutions.contains(specifier)
-      || (specifier.scheme() == "file" && specifier.path().ends_with(".cjs"))
-    {
+    let media_type = MediaType::from_specifier(specifier);
+    if media_type.is_emittable() {
+      return Err(AnyError::from(NotSupportedKindInNpmError {
+        media_type,
+        specifier: specifier.clone(),
+      }));
+    }
+
+    let code = if self.cjs_tracker.is_maybe_cjs(specifier, media_type)? {
       // translate cjs to esm if it's cjs and inject node globals
-      let code = match String::from_utf8_lossy(&code) {
-        Cow::Owned(code) => code,
-        // SAFETY: `String::from_utf8_lossy` guarantees that the result is valid
-        // UTF-8 if `Cow::Borrowed` is returned.
-        Cow::Borrowed(_) => unsafe { String::from_utf8_unchecked(code) },
-      };
+      let code = from_utf8_lossy_owned(code);
       ModuleSourceCode::String(
         self
           .node_code_translator
-          .translate_cjs_to_esm(specifier, Some(code))
+          .translate_cjs_to_esm(specifier, Some(Cow::Owned(code)))
           .await?
+          .into_owned()
           .into(),
       )
     } else {
       // esm and json code is untouched
       ModuleSourceCode::Bytes(code.into_boxed_slice().into())
     };
+
     Ok(ModuleCodeStringSource {
       code,
       found_url: specifier.clone(),
@@ -447,17 +419,165 @@ impl NpmModuleLoader {
   }
 }
 
-/// Keeps track of what module specifiers were resolved as CJS.
-#[derive(Debug, Default)]
-pub struct CjsResolutionStore(DashSet<ModuleSpecifier>);
+pub struct CjsTrackerOptions {
+  pub unstable_detect_cjs: bool,
+}
 
-impl CjsResolutionStore {
-  pub fn contains(&self, specifier: &ModuleSpecifier) -> bool {
-    self.0.contains(specifier)
+/// Keeps track of what module specifiers were resolved as CJS.
+///
+/// Modules that are `.js` or `.ts` are only known to be CJS or
+/// ESM after they're loaded based on their contents. So these files
+/// will be "maybe CJS" until they're loaded.
+#[derive(Debug)]
+pub struct CjsTracker {
+  in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
+  unstable_detect_cjs: bool,
+  known: DashMap<ModuleSpecifier, ModuleKind>,
+}
+
+impl CjsTracker {
+  pub fn new(
+    in_npm_pkg_checker: Arc<dyn InNpmPackageChecker>,
+    pkg_json_resolver: Arc<PackageJsonResolver>,
+    options: CjsTrackerOptions,
+  ) -> Self {
+    Self {
+      in_npm_pkg_checker,
+      pkg_json_resolver,
+      unstable_detect_cjs: options.unstable_detect_cjs,
+      known: Default::default(),
+    }
   }
 
-  pub fn insert(&self, specifier: ModuleSpecifier) {
-    self.0.insert(specifier);
+  /// Checks whether the file might be treated as CJS, but it's not for sure
+  /// yet because the source hasn't been loaded to see whether it contains
+  /// imports or exports.
+  pub fn is_maybe_cjs(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+  ) -> Result<bool, ClosestPkgJsonError> {
+    self.treat_as_cjs_with_is_script(specifier, media_type, None)
+  }
+
+  /// Gets whether the file is CJS. If true, this is for sure
+  /// cjs because `is_script` is provided.
+  ///
+  /// `is_script` should be `true` when the contents of the file at the
+  /// provided specifier are known to be a script and not an ES module.
+  pub fn is_cjs_with_known_is_script(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    is_script: bool,
+  ) -> Result<bool, ClosestPkgJsonError> {
+    self.treat_as_cjs_with_is_script(specifier, media_type, Some(is_script))
+  }
+
+  fn treat_as_cjs_with_is_script(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    is_script: Option<bool>,
+  ) -> Result<bool, ClosestPkgJsonError> {
+    let kind = match self
+      .get_known_kind_with_is_script(specifier, media_type, is_script)
+    {
+      Some(kind) => kind,
+      None => self.check_based_on_pkg_json(specifier)?,
+    };
+    Ok(kind.is_cjs())
+  }
+
+  pub fn get_known_kind(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+  ) -> Option<ModuleKind> {
+    self.get_known_kind_with_is_script(specifier, media_type, None)
+  }
+
+  fn get_known_kind_with_is_script(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    is_script: Option<bool>,
+  ) -> Option<ModuleKind> {
+    if specifier.scheme() != "file" {
+      return Some(ModuleKind::Esm);
+    }
+
+    match media_type {
+      MediaType::Mts | MediaType::Mjs | MediaType::Dmts => Some(ModuleKind::Esm),
+      MediaType::Cjs | MediaType::Cts | MediaType::Dcts => Some(ModuleKind::Cjs),
+      MediaType::Dts => {
+        // dts files are always determined based on the package.json because
+        // they contain imports/exports even when considered CJS
+        if let Some(value) = self.known.get(specifier).map(|v| *v) {
+          Some(value)
+        } else {
+          let value = self.check_based_on_pkg_json(specifier).ok();
+          if let Some(value) = value {
+            self.known.insert(specifier.clone(), value);
+          }
+          Some(value.unwrap_or(ModuleKind::Esm))
+        }
+      }
+      MediaType::Wasm |
+      MediaType::Json => Some(ModuleKind::Esm),
+      MediaType::JavaScript
+      | MediaType::Jsx
+      | MediaType::TypeScript
+      | MediaType::Tsx
+      // treat these as unknown
+      | MediaType::Css
+      | MediaType::SourceMap
+      | MediaType::Unknown => {
+        if let Some(value) = self.known.get(specifier).map(|v| *v) {
+          if value.is_cjs() && is_script == Some(false) {
+            // we now know this is actually esm
+            self.known.insert(specifier.clone(), ModuleKind::Esm);
+            Some(ModuleKind::Esm)
+          } else {
+            Some(value)
+          }
+        } else if is_script == Some(false) {
+          // we know this is esm
+          self.known.insert(specifier.clone(), ModuleKind::Esm);
+          Some(ModuleKind::Esm)
+        } else {
+          None
+        }
+      }
+    }
+  }
+
+  fn check_based_on_pkg_json(
+    &self,
+    specifier: &ModuleSpecifier,
+  ) -> Result<ModuleKind, ClosestPkgJsonError> {
+    if self.in_npm_pkg_checker.in_npm_package(specifier) {
+      if let Some(pkg_json) =
+        self.pkg_json_resolver.get_closest_package_json(specifier)?
+      {
+        let is_file_location_cjs = pkg_json.typ != "module";
+        Ok(ModuleKind::from_is_cjs(is_file_location_cjs))
+      } else {
+        Ok(ModuleKind::Cjs)
+      }
+    } else if self.unstable_detect_cjs {
+      if let Some(pkg_json) =
+        self.pkg_json_resolver.get_closest_package_json(specifier)?
+      {
+        let is_cjs_type = pkg_json.typ == "commonjs";
+        Ok(ModuleKind::from_is_cjs(is_cjs_type))
+      } else {
+        Ok(ModuleKind::Esm)
+      }
+    } else {
+      Ok(ModuleKind::Esm)
+    }
   }
 }
 
@@ -641,8 +761,7 @@ impl Resolver for CliGraphResolver {
             Some(referrer),
             to_node_mode(mode),
           )
-          .map_err(ResolveError::Other)
-          .map(|res| res.into_url()),
+          .map_err(|e| ResolveError::Other(e.into())),
         MappedResolution::PackageJson {
           dep_result,
           alias,
@@ -673,19 +792,17 @@ impl Resolver for CliGraphResolver {
                 )
                 .map_err(|e| ResolveError::Other(e.into()))
                 .and_then(|pkg_folder| {
-                  Ok(
-                    self
-                      .node_resolver
-                      .as_ref()
-                      .unwrap()
-                      .resolve_package_sub_path_from_deno_module(
-                        pkg_folder,
-                        sub_path.as_deref(),
-                        Some(referrer),
-                        to_node_mode(mode),
-                      )?
-                      .into_url(),
-                  )
+                  self
+                    .node_resolver
+                    .as_ref()
+                    .unwrap()
+                    .resolve_package_sub_path_from_deno_module(
+                      pkg_folder,
+                      sub_path.as_deref(),
+                      Some(referrer),
+                      to_node_mode(mode),
+                    )
+                    .map_err(|e| ResolveError::Other(e.into()))
                 }),
             })
         }
@@ -725,23 +842,20 @@ impl Resolver for CliGraphResolver {
               npm_req_ref.req(),
             )
           {
-            return Ok(
-              node_resolver
-                .resolve_package_sub_path_from_deno_module(
-                  pkg_folder,
-                  npm_req_ref.sub_path(),
-                  Some(referrer),
-                  to_node_mode(mode),
-                )?
-                .into_url(),
-            );
+            return node_resolver
+              .resolve_package_sub_path_from_deno_module(
+                pkg_folder,
+                npm_req_ref.sub_path(),
+                Some(referrer),
+                to_node_mode(mode),
+              )
+              .map_err(|e| ResolveError::Other(e.into()));
           }
 
           // do npm resolution for byonm
           if is_byonm {
             return node_resolver
               .resolve_req_reference(&npm_req_ref, referrer, to_node_mode(mode))
-              .map(|res| res.into_url())
               .map_err(|err| err.into());
           }
         }
@@ -759,9 +873,7 @@ impl Resolver for CliGraphResolver {
             .map_err(ResolveError::Other)?;
           if let Some(res) = maybe_resolution {
             match res {
-              NodeResolution::Esm(url) | NodeResolution::CommonJs(url) => {
-                return Ok(url)
-              }
+              NodeResolution::Module(url) => return Ok(url),
               NodeResolution::BuiltIn(_) => {
                 // don't resolve bare specifiers for built-in modules via node resolution
               }
diff --git a/cli/schemas/config-file.v1.json b/cli/schemas/config-file.v1.json
index af18e6f21c..27c8499ea2 100644
--- a/cli/schemas/config-file.v1.json
+++ b/cli/schemas/config-file.v1.json
@@ -291,7 +291,7 @@
               "type": "array",
               "description": "List of tag names that will be run. Empty list disables all tags and will only use rules from `include`.",
               "items": {
-                "type": "string"
+                "$ref": "https://raw.githubusercontent.com/denoland/deno_lint/main/schemas/tags.v1.json"
               },
               "minItems": 0,
               "uniqueItems": true
@@ -300,7 +300,7 @@
               "type": "array",
               "description": "List of rule names that will be excluded from configured tag sets. If the same rule is in `include` it will be run.",
               "items": {
-                "type": "string"
+                "$ref": "https://raw.githubusercontent.com/denoland/deno_lint/main/schemas/rules.v1.json"
               },
               "minItems": 0,
               "uniqueItems": true
@@ -309,7 +309,7 @@
               "type": "array",
               "description": "List of rule names that will be run. Even if the same rule is in `exclude` it will be run.",
               "items": {
-                "type": "string"
+                "$ref": "https://raw.githubusercontent.com/denoland/deno_lint/main/schemas/rules.v1.json"
               },
               "minItems": 0,
               "uniqueItems": true
@@ -528,8 +528,10 @@
           "bare-node-builtins",
           "byonm",
           "cron",
+          "detect-cjs",
           "ffi",
           "fs",
+          "fmt-component",
           "http",
           "kv",
           "net",
diff --git a/cli/standalone/binary.rs b/cli/standalone/binary.rs
index 1290a238f3..9e26512268 100644
--- a/cli/standalone/binary.rs
+++ b/cli/standalone/binary.rs
@@ -9,14 +9,19 @@ use std::ffi::OsString;
 use std::fs;
 use std::fs::File;
 use std::future::Future;
+use std::io::ErrorKind;
 use std::io::Read;
 use std::io::Seek;
 use std::io::SeekFrom;
 use std::io::Write;
+use std::ops::Range;
 use std::path::Path;
 use std::path::PathBuf;
 use std::process::Command;
+use std::sync::Arc;
 
+use deno_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_ast::ModuleSpecifier;
 use deno_config::workspace::PackageJsonDepResolution;
 use deno_config::workspace::ResolverWorkspaceJsrPackage;
@@ -30,13 +35,22 @@ use deno_core::futures::AsyncReadExt;
 use deno_core::futures::AsyncSeekExt;
 use deno_core::serde_json;
 use deno_core::url::Url;
+use deno_graph::source::RealFileSystem;
+use deno_graph::ModuleGraph;
+use deno_npm::resolution::SerializedNpmResolutionSnapshot;
+use deno_npm::resolution::SerializedNpmResolutionSnapshotPackage;
+use deno_npm::resolution::ValidSerializedNpmResolutionSnapshot;
+use deno_npm::NpmPackageId;
 use deno_npm::NpmSystemInfo;
+use deno_runtime::deno_fs;
+use deno_runtime::deno_fs::FileSystem;
+use deno_runtime::deno_fs::RealFs;
+use deno_runtime::deno_io::fs::FsError;
 use deno_runtime::deno_node::PackageJson;
 use deno_semver::npm::NpmVersionReqParseError;
 use deno_semver::package::PackageReq;
 use deno_semver::Version;
 use deno_semver::VersionReqSpecifierParseError;
-use eszip::EszipRelativeFileBaseUrl;
 use indexmap::IndexMap;
 use log::Level;
 use serde::Deserialize;
@@ -49,10 +63,12 @@ use crate::args::NpmInstallDepsProvider;
 use crate::args::PermissionFlags;
 use crate::args::UnstableConfig;
 use crate::cache::DenoDir;
+use crate::emit::Emitter;
 use crate::file_fetcher::FileFetcher;
 use crate::http_util::HttpClientProvider;
 use crate::npm::CliNpmResolver;
 use crate::npm::InnerCliNpmResolverRef;
+use crate::resolver::CjsTracker;
 use crate::shared::ReleaseChannel;
 use crate::standalone::virtual_fs::VfsEntry;
 use crate::util::archive;
@@ -60,12 +76,63 @@ use crate::util::fs::canonicalize_path_maybe_not_exists;
 use crate::util::progress_bar::ProgressBar;
 use crate::util::progress_bar::ProgressBarStyle;
 
+use super::file_system::DenoCompileFileSystem;
+use super::serialization::deserialize_binary_data_section;
+use super::serialization::serialize_binary_data_section;
+use super::serialization::DenoCompileModuleData;
+use super::serialization::DeserializedDataSection;
+use super::serialization::RemoteModulesStore;
+use super::serialization::RemoteModulesStoreBuilder;
 use super::virtual_fs::FileBackedVfs;
 use super::virtual_fs::VfsBuilder;
 use super::virtual_fs::VfsRoot;
 use super::virtual_fs::VirtualDirectory;
 
-const MAGIC_TRAILER: &[u8; 8] = b"d3n0l4nd";
+/// A URL that can be designated as the base for relative URLs.
+///
+/// After creation, this URL may be used to get the key for a
+/// module in the binary.
+#[derive(Debug, Clone, Copy, PartialEq, Eq, Hash)]
+pub struct StandaloneRelativeFileBaseUrl<'a>(&'a Url);
+
+impl<'a> From<&'a Url> for StandaloneRelativeFileBaseUrl<'a> {
+  fn from(url: &'a Url) -> Self {
+    Self(url)
+  }
+}
+
+impl<'a> StandaloneRelativeFileBaseUrl<'a> {
+  pub fn new(url: &'a Url) -> Self {
+    debug_assert_eq!(url.scheme(), "file");
+    Self(url)
+  }
+
+  /// Gets the module map key of the provided specifier.
+  ///
+  /// * Descendant file specifiers will be made relative to the base.
+  /// * Non-descendant file specifiers will stay as-is (absolute).
+  /// * Non-file specifiers will stay as-is.
+  pub fn specifier_key<'b>(&self, target: &'b Url) -> Cow<'b, str> {
+    if target.scheme() != "file" {
+      return Cow::Borrowed(target.as_str());
+    }
+
+    match self.0.make_relative(target) {
+      Some(relative) => {
+        if relative.starts_with("../") {
+          Cow::Borrowed(target.as_str())
+        } else {
+          Cow::Owned(relative)
+        }
+      }
+      None => Cow::Borrowed(target.as_str()),
+    }
+  }
+
+  pub fn inner(&self) -> &Url {
+    self.0
+  }
+}
 
 #[derive(Deserialize, Serialize)]
 pub enum NodeModules {
@@ -120,78 +187,23 @@ pub struct Metadata {
   pub unstable_config: UnstableConfig,
 }
 
-pub fn load_npm_vfs(root_dir_path: PathBuf) -> Result<FileBackedVfs, AnyError> {
-  let data = libsui::find_section("d3n0l4nd").unwrap();
-
-  // We do the first part sync so it can complete quickly
-  let trailer: [u8; TRAILER_SIZE] = data[0..TRAILER_SIZE].try_into().unwrap();
-  let trailer = match Trailer::parse(&trailer)? {
-    None => panic!("Could not find trailer"),
-    Some(trailer) => trailer,
-  };
-  let data = &data[TRAILER_SIZE..];
-
-  let vfs_data =
-    &data[trailer.npm_vfs_pos as usize..trailer.npm_files_pos as usize];
-  let mut dir: VirtualDirectory = serde_json::from_slice(vfs_data)?;
-
-  // align the name of the directory with the root dir
-  dir.name = root_dir_path
-    .file_name()
-    .unwrap()
-    .to_string_lossy()
-    .to_string();
-
-  let fs_root = VfsRoot {
-    dir,
-    root_path: root_dir_path,
-    start_file_offset: trailer.npm_files_pos,
-  };
-  Ok(FileBackedVfs::new(data.to_vec(), fs_root))
-}
-
 fn write_binary_bytes(
   mut file_writer: File,
   original_bin: Vec<u8>,
   metadata: &Metadata,
-  eszip: eszip::EszipV2,
-  npm_vfs: Option<&VirtualDirectory>,
-  npm_files: &Vec<Vec<u8>>,
+  npm_snapshot: Option<SerializedNpmResolutionSnapshot>,
+  remote_modules: &RemoteModulesStoreBuilder,
+  vfs: VfsBuilder,
   compile_flags: &CompileFlags,
 ) -> Result<(), AnyError> {
-  let metadata = serde_json::to_string(metadata)?.as_bytes().to_vec();
-  let npm_vfs = serde_json::to_string(&npm_vfs)?.as_bytes().to_vec();
-  let eszip_archive = eszip.into_bytes();
-
-  let mut writer = Vec::new();
-
-  // write the trailer, which includes the positions
-  // of the data blocks in the file
-  writer.write_all(&{
-    let metadata_pos = eszip_archive.len() as u64;
-    let npm_vfs_pos = metadata_pos + (metadata.len() as u64);
-    let npm_files_pos = npm_vfs_pos + (npm_vfs.len() as u64);
-    Trailer {
-      eszip_pos: 0,
-      metadata_pos,
-      npm_vfs_pos,
-      npm_files_pos,
-    }
-    .as_bytes()
-  })?;
-
-  writer.write_all(&eszip_archive)?;
-  writer.write_all(&metadata)?;
-  writer.write_all(&npm_vfs)?;
-  for file in npm_files {
-    writer.write_all(file)?;
-  }
+  let data_section_bytes =
+    serialize_binary_data_section(metadata, npm_snapshot, remote_modules, vfs)?;
 
   let target = compile_flags.resolve_target();
   if target.contains("linux") {
     libsui::Elf::new(&original_bin).append(
       "d3n0l4nd",
-      &writer,
+      &data_section_bytes,
       &mut file_writer,
     )?;
   } else if target.contains("windows") {
@@ -201,11 +213,11 @@ fn write_binary_bytes(
       pe = pe.set_icon(&icon)?;
     }
 
-    pe.write_resource("d3n0l4nd", writer)?
+    pe.write_resource("d3n0l4nd", data_section_bytes)?
       .build(&mut file_writer)?;
   } else if target.contains("darwin") {
     libsui::Macho::from(original_bin)?
-      .write_section("d3n0l4nd", writer)?
+      .write_section("d3n0l4nd", data_section_bytes)?
       .build_and_sign(&mut file_writer)?;
   }
   Ok(())
@@ -221,6 +233,67 @@ pub fn is_standalone_binary(exe_path: &Path) -> bool {
     || libsui::utils::is_macho(&data)
 }
 
+pub struct StandaloneData {
+  pub fs: Arc<dyn deno_fs::FileSystem>,
+  pub metadata: Metadata,
+  pub modules: StandaloneModules,
+  pub npm_snapshot: Option<ValidSerializedNpmResolutionSnapshot>,
+  pub root_path: PathBuf,
+  pub vfs: Arc<FileBackedVfs>,
+}
+
+pub struct StandaloneModules {
+  remote_modules: RemoteModulesStore,
+  vfs: Arc<FileBackedVfs>,
+}
+
+impl StandaloneModules {
+  pub fn resolve_specifier<'a>(
+    &'a self,
+    specifier: &'a ModuleSpecifier,
+  ) -> Result<Option<&'a ModuleSpecifier>, AnyError> {
+    if specifier.scheme() == "file" {
+      Ok(Some(specifier))
+    } else {
+      self.remote_modules.resolve_specifier(specifier)
+    }
+  }
+
+  pub fn has_file(&self, path: &Path) -> bool {
+    self.vfs.file_entry(path).is_ok()
+  }
+
+  pub fn read<'a>(
+    &'a self,
+    specifier: &'a ModuleSpecifier,
+  ) -> Result<Option<DenoCompileModuleData<'a>>, AnyError> {
+    if specifier.scheme() == "file" {
+      let path = deno_path_util::url_to_file_path(specifier)?;
+      let bytes = match self.vfs.file_entry(&path) {
+        Ok(entry) => self.vfs.read_file_all(entry)?,
+        Err(err) if err.kind() == ErrorKind::NotFound => {
+          let bytes = match RealFs.read_file_sync(&path, None) {
+            Ok(bytes) => bytes,
+            Err(FsError::Io(err)) if err.kind() == ErrorKind::NotFound => {
+              return Ok(None)
+            }
+            Err(err) => return Err(err.into()),
+          };
+          Cow::Owned(bytes)
+        }
+        Err(err) => return Err(err.into()),
+      };
+      Ok(Some(DenoCompileModuleData {
+        media_type: MediaType::from_specifier(specifier),
+        specifier,
+        data: bytes,
+      }))
+    } else {
+      self.remote_modules.read(specifier)
+    }
+  }
+}
+
 /// This function will try to run this binary as a standalone binary
 /// produced by `deno compile`. It determines if this is a standalone
 /// binary by skipping over the trailer width at the end of the file,
@@ -228,110 +301,67 @@ pub fn is_standalone_binary(exe_path: &Path) -> bool {
 /// the bundle is executed. If not, this function exits with `Ok(None)`.
 pub fn extract_standalone(
   cli_args: Cow<Vec<OsString>>,
-) -> Result<
-  Option<impl Future<Output = Result<(Metadata, eszip::EszipV2), AnyError>>>,
-  AnyError,
-> {
+) -> Result<Option<StandaloneData>, AnyError> {
   let Some(data) = libsui::find_section("d3n0l4nd") else {
     return Ok(None);
   };
 
-  // We do the first part sync so it can complete quickly
-  let trailer = match Trailer::parse(&data[0..TRAILER_SIZE])? {
+  let DeserializedDataSection {
+    mut metadata,
+    npm_snapshot,
+    remote_modules,
+    mut vfs_dir,
+    vfs_files_data,
+  } = match deserialize_binary_data_section(data)? {
+    Some(data_section) => data_section,
     None => return Ok(None),
-    Some(trailer) => trailer,
   };
 
+  let root_path = {
+    let maybe_current_exe = std::env::current_exe().ok();
+    let current_exe_name = maybe_current_exe
+      .as_ref()
+      .and_then(|p| p.file_name())
+      .map(|p| p.to_string_lossy())
+      // should never happen
+      .unwrap_or_else(|| Cow::Borrowed("binary"));
+    std::env::temp_dir().join(format!("deno-compile-{}", current_exe_name))
+  };
   let cli_args = cli_args.into_owned();
-  // If we have an eszip, read it out
-  Ok(Some(async move {
-    let bufreader =
-      deno_core::futures::io::BufReader::new(&data[TRAILER_SIZE..]);
+  metadata.argv.reserve(cli_args.len() - 1);
+  for arg in cli_args.into_iter().skip(1) {
+    metadata.argv.push(arg.into_string().unwrap());
+  }
+  let vfs = {
+    // align the name of the directory with the root dir
+    vfs_dir.name = root_path.file_name().unwrap().to_string_lossy().to_string();
 
-    let (eszip, loader) = eszip::EszipV2::parse(bufreader)
-      .await
-      .context("Failed to parse eszip header")?;
-
-    let bufreader = loader.await.context("Failed to parse eszip archive")?;
-
-    let mut metadata = String::new();
-
-    bufreader
-      .take(trailer.metadata_len())
-      .read_to_string(&mut metadata)
-      .await
-      .context("Failed to read metadata from the current executable")?;
-
-    let mut metadata: Metadata = serde_json::from_str(&metadata).unwrap();
-    metadata.argv.reserve(cli_args.len() - 1);
-    for arg in cli_args.into_iter().skip(1) {
-      metadata.argv.push(arg.into_string().unwrap());
-    }
-
-    Ok((metadata, eszip))
+    let fs_root = VfsRoot {
+      dir: vfs_dir,
+      root_path: root_path.clone(),
+      start_file_offset: 0,
+    };
+    Arc::new(FileBackedVfs::new(Cow::Borrowed(vfs_files_data), fs_root))
+  };
+  let fs: Arc<dyn deno_fs::FileSystem> =
+    Arc::new(DenoCompileFileSystem::new(vfs.clone()));
+  Ok(Some(StandaloneData {
+    fs,
+    metadata,
+    modules: StandaloneModules {
+      remote_modules,
+      vfs: vfs.clone(),
+    },
+    npm_snapshot,
+    root_path,
+    vfs,
   }))
 }
 
-const TRAILER_SIZE: usize = std::mem::size_of::<Trailer>() + 8; // 8 bytes for the magic trailer string
-
-struct Trailer {
-  eszip_pos: u64,
-  metadata_pos: u64,
-  npm_vfs_pos: u64,
-  npm_files_pos: u64,
-}
-
-impl Trailer {
-  pub fn parse(trailer: &[u8]) -> Result<Option<Trailer>, AnyError> {
-    let (magic_trailer, rest) = trailer.split_at(8);
-    if magic_trailer != MAGIC_TRAILER {
-      return Ok(None);
-    }
-
-    let (eszip_archive_pos, rest) = rest.split_at(8);
-    let (metadata_pos, rest) = rest.split_at(8);
-    let (npm_vfs_pos, npm_files_pos) = rest.split_at(8);
-    let eszip_archive_pos = u64_from_bytes(eszip_archive_pos)?;
-    let metadata_pos = u64_from_bytes(metadata_pos)?;
-    let npm_vfs_pos = u64_from_bytes(npm_vfs_pos)?;
-    let npm_files_pos = u64_from_bytes(npm_files_pos)?;
-    Ok(Some(Trailer {
-      eszip_pos: eszip_archive_pos,
-      metadata_pos,
-      npm_vfs_pos,
-      npm_files_pos,
-    }))
-  }
-
-  pub fn metadata_len(&self) -> u64 {
-    self.npm_vfs_pos - self.metadata_pos
-  }
-
-  pub fn npm_vfs_len(&self) -> u64 {
-    self.npm_files_pos - self.npm_vfs_pos
-  }
-
-  pub fn as_bytes(&self) -> Vec<u8> {
-    let mut trailer = MAGIC_TRAILER.to_vec();
-    trailer.write_all(&self.eszip_pos.to_be_bytes()).unwrap();
-    trailer.write_all(&self.metadata_pos.to_be_bytes()).unwrap();
-    trailer.write_all(&self.npm_vfs_pos.to_be_bytes()).unwrap();
-    trailer
-      .write_all(&self.npm_files_pos.to_be_bytes())
-      .unwrap();
-    trailer
-  }
-}
-
-fn u64_from_bytes(arr: &[u8]) -> Result<u64, AnyError> {
-  let fixed_arr: &[u8; 8] = arr
-    .try_into()
-    .context("Failed to convert the buffer into a fixed-size array")?;
-  Ok(u64::from_be_bytes(*fixed_arr))
-}
-
 pub struct DenoCompileBinaryWriter<'a> {
+  cjs_tracker: &'a CjsTracker,
   deno_dir: &'a DenoDir,
+  emitter: &'a Emitter,
   file_fetcher: &'a FileFetcher,
   http_client_provider: &'a HttpClientProvider,
   npm_resolver: &'a dyn CliNpmResolver,
@@ -342,7 +372,9 @@ pub struct DenoCompileBinaryWriter<'a> {
 impl<'a> DenoCompileBinaryWriter<'a> {
   #[allow(clippy::too_many_arguments)]
   pub fn new(
+    cjs_tracker: &'a CjsTracker,
     deno_dir: &'a DenoDir,
+    emitter: &'a Emitter,
     file_fetcher: &'a FileFetcher,
     http_client_provider: &'a HttpClientProvider,
     npm_resolver: &'a dyn CliNpmResolver,
@@ -350,7 +382,9 @@ impl<'a> DenoCompileBinaryWriter<'a> {
     npm_system_info: NpmSystemInfo,
   ) -> Self {
     Self {
+      cjs_tracker,
       deno_dir,
+      emitter,
       file_fetcher,
       http_client_provider,
       npm_resolver,
@@ -362,8 +396,8 @@ impl<'a> DenoCompileBinaryWriter<'a> {
   pub async fn write_bin(
     &self,
     writer: File,
-    eszip: eszip::EszipV2,
-    root_dir_url: EszipRelativeFileBaseUrl<'_>,
+    graph: &ModuleGraph,
+    root_dir_url: StandaloneRelativeFileBaseUrl<'_>,
     entrypoint: &ModuleSpecifier,
     compile_flags: &CompileFlags,
     cli_options: &CliOptions,
@@ -390,15 +424,17 @@ impl<'a> DenoCompileBinaryWriter<'a> {
         )
       }
     }
-    self.write_standalone_binary(
-      writer,
-      original_binary,
-      eszip,
-      root_dir_url,
-      entrypoint,
-      cli_options,
-      compile_flags,
-    )
+    self
+      .write_standalone_binary(
+        writer,
+        original_binary,
+        graph,
+        root_dir_url,
+        entrypoint,
+        cli_options,
+        compile_flags,
+      )
+      .await
   }
 
   async fn get_base_binary(
@@ -468,7 +504,11 @@ impl<'a> DenoCompileBinaryWriter<'a> {
       self
         .http_client_provider
         .get_or_create()?
-        .download_with_progress(download_url.parse()?, None, &progress)
+        .download_with_progress_and_retries(
+          download_url.parse()?,
+          None,
+          &progress,
+        )
         .await?
     };
     let bytes = match maybe_bytes {
@@ -489,12 +529,12 @@ impl<'a> DenoCompileBinaryWriter<'a> {
   /// This functions creates a standalone deno binary by appending a bundle
   /// and magic trailer to the currently executing binary.
   #[allow(clippy::too_many_arguments)]
-  fn write_standalone_binary(
+  async fn write_standalone_binary(
     &self,
     writer: File,
     original_bin: Vec<u8>,
-    mut eszip: eszip::EszipV2,
-    root_dir_url: EszipRelativeFileBaseUrl<'_>,
+    graph: &ModuleGraph,
+    root_dir_url: StandaloneRelativeFileBaseUrl<'_>,
     entrypoint: &ModuleSpecifier,
     cli_options: &CliOptions,
     compile_flags: &CompileFlags,
@@ -508,19 +548,17 @@ impl<'a> DenoCompileBinaryWriter<'a> {
       None => None,
     };
     let root_path = root_dir_url.inner().to_file_path().unwrap();
-    let (npm_vfs, npm_files, node_modules) = match self.npm_resolver.as_inner()
+    let (maybe_npm_vfs, node_modules, npm_snapshot) = match self
+      .npm_resolver
+      .as_inner()
     {
       InnerCliNpmResolverRef::Managed(managed) => {
         let snapshot =
           managed.serialized_valid_snapshot_for_system(&self.npm_system_info);
         if !snapshot.as_serialized().packages.is_empty() {
-          let (root_dir, files) = self
-            .build_vfs(&root_path, cli_options)?
-            .into_dir_and_files();
-          eszip.add_npm_snapshot(snapshot);
+          let npm_vfs_builder = self.build_npm_vfs(&root_path, cli_options)?;
           (
-            Some(root_dir),
-            files,
+            Some(npm_vfs_builder),
             Some(NodeModules::Managed {
               node_modules_dir: self.npm_resolver.root_node_modules_path().map(
                 |path| {
@@ -532,18 +570,16 @@ impl<'a> DenoCompileBinaryWriter<'a> {
                 },
               ),
             }),
+            Some(snapshot),
           )
         } else {
-          (None, Vec::new(), None)
+          (None, None, None)
         }
       }
       InnerCliNpmResolverRef::Byonm(resolver) => {
-        let (root_dir, files) = self
-          .build_vfs(&root_path, cli_options)?
-          .into_dir_and_files();
+        let npm_vfs_builder = self.build_npm_vfs(&root_path, cli_options)?;
         (
-          Some(root_dir),
-          files,
+          Some(npm_vfs_builder),
           Some(NodeModules::Byonm {
             root_node_modules_dir: resolver.root_node_modules_path().map(
               |node_modules_dir| {
@@ -556,9 +592,69 @@ impl<'a> DenoCompileBinaryWriter<'a> {
               },
             ),
           }),
+          None,
         )
       }
     };
+    let mut vfs = if let Some(npm_vfs) = maybe_npm_vfs {
+      npm_vfs
+    } else {
+      VfsBuilder::new(root_path.clone())?
+    };
+    let mut remote_modules_store = RemoteModulesStoreBuilder::default();
+    for module in graph.modules() {
+      if module.specifier().scheme() == "data" {
+        continue; // don't store data urls as an entry as they're in the code
+      }
+      let (maybe_source, media_type) = match module {
+        deno_graph::Module::Js(m) => {
+          let source = if m.media_type.is_emittable() {
+            let is_cjs = self.cjs_tracker.is_cjs_with_known_is_script(
+              &m.specifier,
+              m.media_type,
+              m.is_script,
+            )?;
+            let module_kind = ModuleKind::from_is_cjs(is_cjs);
+            let source = self
+              .emitter
+              .emit_parsed_source(
+                &m.specifier,
+                m.media_type,
+                module_kind,
+                &m.source,
+              )
+              .await?;
+            source.into_bytes()
+          } else {
+            m.source.as_bytes().to_vec()
+          };
+          (Some(source), m.media_type)
+        }
+        deno_graph::Module::Json(m) => {
+          (Some(m.source.as_bytes().to_vec()), m.media_type)
+        }
+        deno_graph::Module::Npm(_)
+        | deno_graph::Module::Node(_)
+        | deno_graph::Module::External(_) => (None, MediaType::Unknown),
+      };
+      if module.specifier().scheme() == "file" {
+        let file_path = deno_path_util::url_to_file_path(module.specifier())?;
+        vfs
+          .add_file_with_data(
+            &file_path,
+            match maybe_source {
+              Some(source) => source,
+              None => RealFs.read_file_sync(&file_path, None)?,
+            },
+          )
+          .with_context(|| {
+            format!("Failed adding '{}'", file_path.display())
+          })?;
+      } else if let Some(source) = maybe_source {
+        remote_modules_store.add(module.specifier(), media_type, source);
+      }
+    }
+    remote_modules_store.add_redirects(&graph.redirects);
 
     let env_vars_from_env_file = match cli_options.env_file_name() {
       Some(env_filename) => {
@@ -622,6 +718,7 @@ impl<'a> DenoCompileBinaryWriter<'a> {
       unstable_config: UnstableConfig {
         legacy_flag_enabled: false,
         bare_node_builtins: cli_options.unstable_bare_node_builtins(),
+        detect_cjs: cli_options.unstable_detect_cjs(),
         sloppy_imports: cli_options.unstable_sloppy_imports(),
         features: cli_options.unstable_features(),
       },
@@ -631,14 +728,14 @@ impl<'a> DenoCompileBinaryWriter<'a> {
       writer,
       original_bin,
       &metadata,
-      eszip,
-      npm_vfs.as_ref(),
-      &npm_files,
+      npm_snapshot.map(|s| s.into_serialized()),
+      &remote_modules_store,
+      vfs,
       compile_flags,
     )
   }
 
-  fn build_vfs(
+  fn build_npm_vfs(
     &self,
     root_path: &Path,
     cli_options: &CliOptions,
@@ -659,8 +756,9 @@ impl<'a> DenoCompileBinaryWriter<'a> {
         } else {
           // DO NOT include the user's registry url as it may contain credentials,
           // but also don't make this dependent on the registry url
-          let root_path = npm_resolver.global_cache_root_folder();
-          let mut builder = VfsBuilder::new(root_path)?;
+          let global_cache_root_path = npm_resolver.global_cache_root_path();
+          let mut builder =
+            VfsBuilder::new(global_cache_root_path.to_path_buf())?;
           let mut packages =
             npm_resolver.all_system_packages(&self.npm_system_info);
           packages.sort_by(|a, b| a.id.cmp(&b.id)); // determinism
@@ -670,12 +768,12 @@ impl<'a> DenoCompileBinaryWriter<'a> {
             builder.add_dir_recursive(&folder)?;
           }
 
-          // Flatten all the registries folders into a single "node_modules/localhost" folder
+          // Flatten all the registries folders into a single ".deno_compile_node_modules/localhost" folder
           // that will be used by denort when loading the npm cache. This avoids us exposing
           // the user's private registry information and means we don't have to bother
           // serializing all the different registry config into the binary.
           builder.with_root_dir(|root_dir| {
-            root_dir.name = "node_modules".to_string();
+            root_dir.name = ".deno_compile_node_modules".to_string();
             let mut new_entries = Vec::with_capacity(root_dir.entries.len());
             let mut localhost_entries = IndexMap::new();
             for entry in std::mem::take(&mut root_dir.entries) {
@@ -710,6 +808,8 @@ impl<'a> DenoCompileBinaryWriter<'a> {
             root_dir.entries = new_entries;
           });
 
+          builder.set_new_root_path(root_path.to_path_buf())?;
+
           Ok(builder)
         }
       }
diff --git a/cli/standalone/file_system.rs b/cli/standalone/file_system.rs
index 314444630b..712c6ee918 100644
--- a/cli/standalone/file_system.rs
+++ b/cli/standalone/file_system.rs
@@ -22,8 +22,8 @@ use super::virtual_fs::FileBackedVfs;
 pub struct DenoCompileFileSystem(Arc<FileBackedVfs>);
 
 impl DenoCompileFileSystem {
-  pub fn new(vfs: FileBackedVfs) -> Self {
-    Self(Arc::new(vfs))
+  pub fn new(vfs: Arc<FileBackedVfs>) -> Self {
+    Self(vfs)
   }
 
   fn error_if_in_vfs(&self, path: &Path) -> FsResult<()> {
diff --git a/cli/standalone/mod.rs b/cli/standalone/mod.rs
index 258de0dad3..85610f4c20 100644
--- a/cli/standalone/mod.rs
+++ b/cli/standalone/mod.rs
@@ -5,6 +5,8 @@
 #![allow(dead_code)]
 #![allow(unused_imports)]
 
+use binary::StandaloneData;
+use binary::StandaloneModules;
 use deno_ast::MediaType;
 use deno_cache_dir::npm::NpmCacheDir;
 use deno_config::workspace::MappedResolution;
@@ -17,6 +19,7 @@ use deno_core::error::type_error;
 use deno_core::error::AnyError;
 use deno_core::futures::FutureExt;
 use deno_core::v8_set_flags;
+use deno_core::FastString;
 use deno_core::FeatureChecker;
 use deno_core::ModuleLoader;
 use deno_core::ModuleSourceCode;
@@ -28,7 +31,9 @@ use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_package_json::PackageJsonDepValue;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::create_host_defined_options;
+use deno_runtime::deno_node::NodeRequireLoader;
 use deno_runtime::deno_node::NodeResolver;
+use deno_runtime::deno_node::PackageJsonResolver;
 use deno_runtime::deno_permissions::Permissions;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::deno_tls::rustls::RootCertStore;
@@ -38,10 +43,10 @@ use deno_runtime::permissions::RuntimePermissionDescriptorParser;
 use deno_runtime::WorkerExecutionMode;
 use deno_runtime::WorkerLogLevel;
 use deno_semver::npm::NpmPackageReqReference;
-use eszip::EszipRelativeFileBaseUrl;
 use import_map::parse_from_json;
 use node_resolver::analyze::NodeCodeTranslator;
 use node_resolver::NodeResolutionMode;
+use serialization::DenoCompileModuleSource;
 use std::borrow::Cow;
 use std::rc::Rc;
 use std::sync::Arc;
@@ -54,17 +59,24 @@ use crate::args::CacheSetting;
 use crate::args::NpmInstallDepsProvider;
 use crate::args::StorageKeyResolver;
 use crate::cache::Caches;
+use crate::cache::DenoCacheEnvFsAdapter;
 use crate::cache::DenoDirProvider;
 use crate::cache::NodeAnalysisCache;
 use crate::cache::RealDenoCacheEnv;
 use crate::http_util::HttpClientProvider;
 use crate::node::CliCjsCodeAnalyzer;
+use crate::node::CliNodeCodeTranslator;
 use crate::npm::create_cli_npm_resolver;
+use crate::npm::create_in_npm_pkg_checker;
 use crate::npm::CliByonmNpmResolverCreateOptions;
+use crate::npm::CliManagedInNpmPkgCheckerCreateOptions;
+use crate::npm::CliManagedNpmResolverCreateOptions;
+use crate::npm::CliNpmResolver;
 use crate::npm::CliNpmResolverCreateOptions;
-use crate::npm::CliNpmResolverManagedCreateOptions;
 use crate::npm::CliNpmResolverManagedSnapshotOption;
-use crate::resolver::CjsResolutionStore;
+use crate::npm::CreateInNpmPkgCheckerOptions;
+use crate::resolver::CjsTracker;
+use crate::resolver::CjsTrackerOptions;
 use crate::resolver::CliDenoResolverFs;
 use crate::resolver::CliNodeResolver;
 use crate::resolver::NpmModuleLoader;
@@ -73,60 +85,30 @@ use crate::util::progress_bar::ProgressBarStyle;
 use crate::util::v8::construct_v8_flags;
 use crate::worker::CliMainWorkerFactory;
 use crate::worker::CliMainWorkerOptions;
-use crate::worker::ModuleLoaderAndSourceMapGetter;
+use crate::worker::CreateModuleLoaderResult;
 use crate::worker::ModuleLoaderFactory;
 
 pub mod binary;
 mod file_system;
+mod serialization;
 mod virtual_fs;
 
 pub use binary::extract_standalone;
 pub use binary::is_standalone_binary;
 pub use binary::DenoCompileBinaryWriter;
 
-use self::binary::load_npm_vfs;
 use self::binary::Metadata;
 use self::file_system::DenoCompileFileSystem;
 
-struct WorkspaceEszipModule {
-  specifier: ModuleSpecifier,
-  inner: eszip::Module,
-}
-
-struct WorkspaceEszip {
-  eszip: eszip::EszipV2,
-  root_dir_url: Arc<ModuleSpecifier>,
-}
-
-impl WorkspaceEszip {
-  pub fn get_module(
-    &self,
-    specifier: &ModuleSpecifier,
-  ) -> Option<WorkspaceEszipModule> {
-    if specifier.scheme() == "file" {
-      let specifier_key = EszipRelativeFileBaseUrl::new(&self.root_dir_url)
-        .specifier_key(specifier);
-      let module = self.eszip.get_module(&specifier_key)?;
-      let specifier = self.root_dir_url.join(&module.specifier).unwrap();
-      Some(WorkspaceEszipModule {
-        specifier,
-        inner: module,
-      })
-    } else {
-      let module = self.eszip.get_module(specifier.as_str())?;
-      Some(WorkspaceEszipModule {
-        specifier: ModuleSpecifier::parse(&module.specifier).unwrap(),
-        inner: module,
-      })
-    }
-  }
-}
-
 struct SharedModuleLoaderState {
-  eszip: WorkspaceEszip,
-  workspace_resolver: WorkspaceResolver,
+  cjs_tracker: Arc<CjsTracker>,
+  fs: Arc<dyn deno_fs::FileSystem>,
+  modules: StandaloneModules,
+  node_code_translator: Arc<CliNodeCodeTranslator>,
   node_resolver: Arc<CliNodeResolver>,
   npm_module_loader: Arc<NpmModuleLoader>,
+  npm_resolver: Arc<dyn CliNpmResolver>,
+  workspace_resolver: WorkspaceResolver,
 }
 
 #[derive(Clone)]
@@ -134,6 +116,12 @@ struct EmbeddedModuleLoader {
   shared: Arc<SharedModuleLoaderState>,
 }
 
+impl std::fmt::Debug for EmbeddedModuleLoader {
+  fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+    f.debug_struct("EmbeddedModuleLoader").finish()
+  }
+}
+
 pub const MODULE_NOT_FOUND: &str = "Module not found";
 pub const UNSUPPORTED_SCHEME: &str = "Unsupported scheme";
 
@@ -191,8 +179,7 @@ impl ModuleLoader for EmbeddedModuleLoader {
             sub_path.as_deref(),
             Some(&referrer),
             NodeResolutionMode::Execution,
-          )?
-          .into_url(),
+          )?,
       ),
       Ok(MappedResolution::PackageJson {
         dep_result,
@@ -200,16 +187,14 @@ impl ModuleLoader for EmbeddedModuleLoader {
         alias,
         ..
       }) => match dep_result.as_ref().map_err(|e| AnyError::from(e.clone()))? {
-        PackageJsonDepValue::Req(req) => self
-          .shared
-          .node_resolver
-          .resolve_req_with_sub_path(
+        PackageJsonDepValue::Req(req) => {
+          self.shared.node_resolver.resolve_req_with_sub_path(
             req,
             sub_path.as_deref(),
             &referrer,
             NodeResolutionMode::Execution,
           )
-          .map(|res| res.into_url()),
+        }
         PackageJsonDepValue::Workspace(version_req) => {
           let pkg_folder = self
             .shared
@@ -227,8 +212,7 @@ impl ModuleLoader for EmbeddedModuleLoader {
                 sub_path.as_deref(),
                 Some(&referrer),
                 NodeResolutionMode::Execution,
-              )?
-              .into_url(),
+              )?,
           )
         }
       },
@@ -237,20 +221,18 @@ impl ModuleLoader for EmbeddedModuleLoader {
         if let Ok(reference) =
           NpmPackageReqReference::from_specifier(&specifier)
         {
-          return self
-            .shared
-            .node_resolver
-            .resolve_req_reference(
-              &reference,
-              &referrer,
-              NodeResolutionMode::Execution,
-            )
-            .map(|res| res.into_url());
+          return self.shared.node_resolver.resolve_req_reference(
+            &reference,
+            &referrer,
+            NodeResolutionMode::Execution,
+          );
         }
 
         if specifier.scheme() == "jsr" {
-          if let Some(module) = self.shared.eszip.get_module(&specifier) {
-            return Ok(module.specifier);
+          if let Some(specifier) =
+            self.shared.modules.resolve_specifier(&specifier)?
+          {
+            return Ok(specifier.clone());
           }
         }
 
@@ -345,82 +327,140 @@ impl ModuleLoader for EmbeddedModuleLoader {
       );
     }
 
-    let Some(module) = self.shared.eszip.get_module(original_specifier) else {
-      return deno_core::ModuleLoadResponse::Sync(Err(type_error(format!(
-        "{MODULE_NOT_FOUND}: {}",
-        original_specifier
-      ))));
-    };
-    let original_specifier = original_specifier.clone();
-
-    deno_core::ModuleLoadResponse::Async(
-      async move {
-        let code = module.inner.source().await.ok_or_else(|| {
-          type_error(format!("Module not found: {}", original_specifier))
-        })?;
-        let code = arc_u8_to_arc_str(code)
-          .map_err(|_| type_error("Module source is not utf-8"))?;
-        Ok(deno_core::ModuleSource::new_with_redirect(
-          match module.inner.kind {
-            eszip::ModuleKind::JavaScript => ModuleType::JavaScript,
-            eszip::ModuleKind::Json => ModuleType::Json,
-            eszip::ModuleKind::Jsonc => {
-              return Err(type_error("jsonc modules not supported"))
+    match self.shared.modules.read(original_specifier) {
+      Ok(Some(module)) => {
+        let media_type = module.media_type;
+        let (module_specifier, module_type, module_source) =
+          module.into_parts();
+        let is_maybe_cjs = match self
+          .shared
+          .cjs_tracker
+          .is_maybe_cjs(original_specifier, media_type)
+        {
+          Ok(is_maybe_cjs) => is_maybe_cjs,
+          Err(err) => {
+            return deno_core::ModuleLoadResponse::Sync(Err(type_error(
+              format!("{:?}", err),
+            )));
+          }
+        };
+        if is_maybe_cjs {
+          let original_specifier = original_specifier.clone();
+          let module_specifier = module_specifier.clone();
+          let shared = self.shared.clone();
+          deno_core::ModuleLoadResponse::Async(
+            async move {
+              let source = match module_source {
+                DenoCompileModuleSource::String(string) => {
+                  Cow::Borrowed(string)
+                }
+                DenoCompileModuleSource::Bytes(module_code_bytes) => {
+                  match module_code_bytes {
+                    Cow::Owned(bytes) => Cow::Owned(
+                      crate::util::text_encoding::from_utf8_lossy_owned(bytes),
+                    ),
+                    Cow::Borrowed(bytes) => String::from_utf8_lossy(bytes),
+                  }
+                }
+              };
+              let source = shared
+                .node_code_translator
+                .translate_cjs_to_esm(&module_specifier, Some(source))
+                .await?;
+              let module_source = match source {
+                Cow::Owned(source) => ModuleSourceCode::String(source.into()),
+                Cow::Borrowed(source) => {
+                  ModuleSourceCode::String(FastString::from_static(source))
+                }
+              };
+              Ok(deno_core::ModuleSource::new_with_redirect(
+                module_type,
+                module_source,
+                &original_specifier,
+                &module_specifier,
+                None,
+              ))
             }
-            eszip::ModuleKind::OpaqueData => {
-              unreachable!();
-            }
-          },
-          ModuleSourceCode::String(code.into()),
-          &original_specifier,
-          &module.specifier,
-          None,
-        ))
+            .boxed_local(),
+          )
+        } else {
+          let module_source = module_source.into_for_v8();
+          deno_core::ModuleLoadResponse::Sync(Ok(
+            deno_core::ModuleSource::new_with_redirect(
+              module_type,
+              module_source,
+              original_specifier,
+              module_specifier,
+              None,
+            ),
+          ))
+        }
       }
-      .boxed_local(),
-    )
+      Ok(None) => deno_core::ModuleLoadResponse::Sync(Err(type_error(
+        format!("{MODULE_NOT_FOUND}: {}", original_specifier),
+      ))),
+      Err(err) => deno_core::ModuleLoadResponse::Sync(Err(type_error(
+        format!("{:?}", err),
+      ))),
+    }
   }
 }
 
-fn arc_u8_to_arc_str(
-  arc_u8: Arc<[u8]>,
-) -> Result<Arc<str>, std::str::Utf8Error> {
-  // Check that the string is valid UTF-8.
-  std::str::from_utf8(&arc_u8)?;
-  // SAFETY: the string is valid UTF-8, and the layout Arc<[u8]> is the same as
-  // Arc<str>. This is proven by the From<Arc<str>> impl for Arc<[u8]> from the
-  // standard library.
-  Ok(unsafe {
-    std::mem::transmute::<std::sync::Arc<[u8]>, std::sync::Arc<str>>(arc_u8)
-  })
+impl NodeRequireLoader for EmbeddedModuleLoader {
+  fn ensure_read_permission<'a>(
+    &self,
+    permissions: &mut dyn deno_runtime::deno_node::NodePermissions,
+    path: &'a std::path::Path,
+  ) -> Result<Cow<'a, std::path::Path>, AnyError> {
+    if self.shared.modules.has_file(path) {
+      // allow reading if the file is in the snapshot
+      return Ok(Cow::Borrowed(path));
+    }
+
+    self
+      .shared
+      .npm_resolver
+      .ensure_read_permission(permissions, path)
+  }
+
+  fn load_text_file_lossy(
+    &self,
+    path: &std::path::Path,
+  ) -> Result<String, AnyError> {
+    Ok(self.shared.fs.read_text_file_lossy_sync(path, None)?)
+  }
 }
 
 struct StandaloneModuleLoaderFactory {
   shared: Arc<SharedModuleLoaderState>,
 }
 
+impl StandaloneModuleLoaderFactory {
+  pub fn create_result(&self) -> CreateModuleLoaderResult {
+    let loader = Rc::new(EmbeddedModuleLoader {
+      shared: self.shared.clone(),
+    });
+    CreateModuleLoaderResult {
+      module_loader: loader.clone(),
+      node_require_loader: loader,
+    }
+  }
+}
+
 impl ModuleLoaderFactory for StandaloneModuleLoaderFactory {
   fn create_for_main(
     &self,
     _root_permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
-    ModuleLoaderAndSourceMapGetter {
-      module_loader: Rc::new(EmbeddedModuleLoader {
-        shared: self.shared.clone(),
-      }),
-    }
+  ) -> CreateModuleLoaderResult {
+    self.create_result()
   }
 
   fn create_for_worker(
     &self,
     _parent_permissions: PermissionsContainer,
     _permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter {
-    ModuleLoaderAndSourceMapGetter {
-      module_loader: Rc::new(EmbeddedModuleLoader {
-        shared: self.shared.clone(),
-      }),
-    }
+  ) -> CreateModuleLoaderResult {
+    self.create_result()
   }
 }
 
@@ -439,13 +479,15 @@ impl RootCertStoreProvider for StandaloneRootCertStoreProvider {
   }
 }
 
-pub async fn run(
-  mut eszip: eszip::EszipV2,
-  metadata: Metadata,
-) -> Result<i32, AnyError> {
-  let current_exe_path = std::env::current_exe().unwrap();
-  let current_exe_name =
-    current_exe_path.file_name().unwrap().to_string_lossy();
+pub async fn run(data: StandaloneData) -> Result<i32, AnyError> {
+  let StandaloneData {
+    fs,
+    metadata,
+    modules,
+    npm_snapshot,
+    root_path,
+    vfs,
+  } = data;
   let deno_dir_provider = Arc::new(DenoDirProvider::new(None));
   let root_cert_store_provider = Arc::new(StandaloneRootCertStoreProvider {
     ca_stores: metadata.ca_stores,
@@ -459,44 +501,50 @@ pub async fn run(
   ));
   // use a dummy npm registry url
   let npm_registry_url = ModuleSpecifier::parse("https://localhost/").unwrap();
-  let root_path =
-    std::env::temp_dir().join(format!("deno-compile-{}", current_exe_name));
   let root_dir_url =
     Arc::new(ModuleSpecifier::from_directory_path(&root_path).unwrap());
   let main_module = root_dir_url.join(&metadata.entrypoint_key).unwrap();
-  let root_node_modules_path = root_path.join("node_modules");
-  let npm_cache_dir = NpmCacheDir::new(
-    &RealDenoCacheEnv,
-    root_node_modules_path.clone(),
-    vec![npm_registry_url.clone()],
-  );
-  let npm_global_cache_dir = npm_cache_dir.get_cache_location();
+  let npm_global_cache_dir = root_path.join(".deno_compile_node_modules");
   let cache_setting = CacheSetting::Only;
-  let (fs, npm_resolver, maybe_vfs_root) = match metadata.node_modules {
+  let pkg_json_resolver = Arc::new(PackageJsonResolver::new(
+    deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+  ));
+  let (in_npm_pkg_checker, npm_resolver) = match metadata.node_modules {
     Some(binary::NodeModules::Managed { node_modules_dir }) => {
-      // this will always have a snapshot
-      let snapshot = eszip.take_npm_snapshot().unwrap();
-      let vfs_root_dir_path = if node_modules_dir.is_some() {
-        root_path.clone()
-      } else {
-        npm_cache_dir.root_dir().to_owned()
-      };
-      let vfs = load_npm_vfs(vfs_root_dir_path.clone())
-        .context("Failed to load npm vfs.")?;
+      // create an npmrc that uses the fake npm_registry_url to resolve packages
+      let npmrc = Arc::new(ResolvedNpmRc {
+        default_config: deno_npm::npm_rc::RegistryConfigWithUrl {
+          registry_url: npm_registry_url.clone(),
+          config: Default::default(),
+        },
+        scopes: Default::default(),
+        registry_configs: Default::default(),
+      });
+      let npm_cache_dir = Arc::new(NpmCacheDir::new(
+        &DenoCacheEnvFsAdapter(fs.as_ref()),
+        npm_global_cache_dir,
+        npmrc.get_all_known_registries_urls(),
+      ));
+      let snapshot = npm_snapshot.unwrap();
       let maybe_node_modules_path = node_modules_dir
-        .map(|node_modules_dir| vfs_root_dir_path.join(node_modules_dir));
-      let fs = Arc::new(DenoCompileFileSystem::new(vfs))
-        as Arc<dyn deno_fs::FileSystem>;
+        .map(|node_modules_dir| root_path.join(node_modules_dir));
+      let in_npm_pkg_checker =
+        create_in_npm_pkg_checker(CreateInNpmPkgCheckerOptions::Managed(
+          CliManagedInNpmPkgCheckerCreateOptions {
+            root_cache_dir_url: npm_cache_dir.root_dir_url(),
+            maybe_node_modules_path: maybe_node_modules_path.as_deref(),
+          },
+        ));
       let npm_resolver =
         create_cli_npm_resolver(CliNpmResolverCreateOptions::Managed(
-          CliNpmResolverManagedCreateOptions {
+          CliManagedNpmResolverCreateOptions {
             snapshot: CliNpmResolverManagedSnapshotOption::Specified(Some(
               snapshot,
             )),
             maybe_lockfile: None,
             fs: fs.clone(),
             http_client_provider: http_client_provider.clone(),
-            npm_global_cache_dir,
+            npm_cache_dir,
             cache_setting,
             text_only_progress_bar: progress_bar,
             maybe_node_modules_path,
@@ -505,50 +553,54 @@ pub async fn run(
               // this is only used for installing packages, which isn't necessary with deno compile
               NpmInstallDepsProvider::empty(),
             ),
-            // create an npmrc that uses the fake npm_registry_url to resolve packages
-            npmrc: Arc::new(ResolvedNpmRc {
-              default_config: deno_npm::npm_rc::RegistryConfigWithUrl {
-                registry_url: npm_registry_url.clone(),
-                config: Default::default(),
-              },
-              scopes: Default::default(),
-              registry_configs: Default::default(),
-            }),
+            npmrc,
             lifecycle_scripts: Default::default(),
           },
         ))
         .await?;
-      (fs, npm_resolver, Some(vfs_root_dir_path))
+      (in_npm_pkg_checker, npm_resolver)
     }
     Some(binary::NodeModules::Byonm {
       root_node_modules_dir,
     }) => {
-      let vfs_root_dir_path = root_path.clone();
-      let vfs = load_npm_vfs(vfs_root_dir_path.clone())
-        .context("Failed to load vfs.")?;
       let root_node_modules_dir =
         root_node_modules_dir.map(|p| vfs.root().join(p));
-      let fs = Arc::new(DenoCompileFileSystem::new(vfs))
-        as Arc<dyn deno_fs::FileSystem>;
+      let in_npm_pkg_checker =
+        create_in_npm_pkg_checker(CreateInNpmPkgCheckerOptions::Byonm);
       let npm_resolver = create_cli_npm_resolver(
         CliNpmResolverCreateOptions::Byonm(CliByonmNpmResolverCreateOptions {
           fs: CliDenoResolverFs(fs.clone()),
+          pkg_json_resolver: pkg_json_resolver.clone(),
           root_node_modules_dir,
         }),
       )
       .await?;
-      (fs, npm_resolver, Some(vfs_root_dir_path))
+      (in_npm_pkg_checker, npm_resolver)
     }
     None => {
-      let fs = Arc::new(deno_fs::RealFs) as Arc<dyn deno_fs::FileSystem>;
+      // Packages from different registries are already inlined in the binary,
+      // so no need to create actual `.npmrc` configuration.
+      let npmrc = create_default_npmrc();
+      let npm_cache_dir = Arc::new(NpmCacheDir::new(
+        &DenoCacheEnvFsAdapter(fs.as_ref()),
+        npm_global_cache_dir,
+        npmrc.get_all_known_registries_urls(),
+      ));
+      let in_npm_pkg_checker =
+        create_in_npm_pkg_checker(CreateInNpmPkgCheckerOptions::Managed(
+          CliManagedInNpmPkgCheckerCreateOptions {
+            root_cache_dir_url: npm_cache_dir.root_dir_url(),
+            maybe_node_modules_path: None,
+          },
+        ));
       let npm_resolver =
         create_cli_npm_resolver(CliNpmResolverCreateOptions::Managed(
-          CliNpmResolverManagedCreateOptions {
+          CliManagedNpmResolverCreateOptions {
             snapshot: CliNpmResolverManagedSnapshotOption::Specified(None),
             maybe_lockfile: None,
             fs: fs.clone(),
             http_client_provider: http_client_provider.clone(),
-            npm_global_cache_dir,
+            npm_cache_dir,
             cache_setting,
             text_only_progress_bar: progress_bar,
             maybe_node_modules_path: None,
@@ -557,41 +609,52 @@ pub async fn run(
               // this is only used for installing packages, which isn't necessary with deno compile
               NpmInstallDepsProvider::empty(),
             ),
-            // Packages from different registries are already inlined in the ESZip,
-            // so no need to create actual `.npmrc` configuration.
             npmrc: create_default_npmrc(),
             lifecycle_scripts: Default::default(),
           },
         ))
         .await?;
-      (fs, npm_resolver, None)
+      (in_npm_pkg_checker, npm_resolver)
     }
   };
 
   let has_node_modules_dir = npm_resolver.root_node_modules_path().is_some();
   let node_resolver = Arc::new(NodeResolver::new(
     deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    in_npm_pkg_checker.clone(),
     npm_resolver.clone().into_npm_resolver(),
+    pkg_json_resolver.clone(),
+  ));
+  let cjs_tracker = Arc::new(CjsTracker::new(
+    in_npm_pkg_checker.clone(),
+    pkg_json_resolver.clone(),
+    CjsTrackerOptions {
+      unstable_detect_cjs: metadata.unstable_config.detect_cjs,
+    },
   ));
-  let cjs_resolutions = Arc::new(CjsResolutionStore::default());
   let cache_db = Caches::new(deno_dir_provider.clone());
   let node_analysis_cache = NodeAnalysisCache::new(cache_db.node_analysis_db());
   let cli_node_resolver = Arc::new(CliNodeResolver::new(
-    cjs_resolutions.clone(),
+    cjs_tracker.clone(),
     fs.clone(),
+    in_npm_pkg_checker.clone(),
     node_resolver.clone(),
     npm_resolver.clone(),
   ));
   let cjs_esm_code_analyzer = CliCjsCodeAnalyzer::new(
     node_analysis_cache,
+    cjs_tracker.clone(),
     fs.clone(),
-    cli_node_resolver.clone(),
+    None,
+    false,
   );
   let node_code_translator = Arc::new(NodeCodeTranslator::new(
     cjs_esm_code_analyzer,
     deno_runtime::deno_node::DenoFsNodeResolverEnv::new(fs.clone()),
+    in_npm_pkg_checker,
     node_resolver.clone(),
     npm_resolver.clone().into_npm_resolver(),
+    pkg_json_resolver.clone(),
   ));
   let workspace_resolver = {
     let import_map = match metadata.workspace_resolver.import_map {
@@ -644,37 +707,35 @@ pub async fn run(
   };
   let module_loader_factory = StandaloneModuleLoaderFactory {
     shared: Arc::new(SharedModuleLoaderState {
-      eszip: WorkspaceEszip {
-        eszip,
-        root_dir_url,
-      },
-      workspace_resolver,
+      cjs_tracker: cjs_tracker.clone(),
+      fs: fs.clone(),
+      modules,
+      node_code_translator: node_code_translator.clone(),
       node_resolver: cli_node_resolver.clone(),
       npm_module_loader: Arc::new(NpmModuleLoader::new(
-        cjs_resolutions,
-        node_code_translator,
+        cjs_tracker.clone(),
         fs.clone(),
-        cli_node_resolver,
+        node_code_translator,
       )),
+      npm_resolver: npm_resolver.clone(),
+      workspace_resolver,
     }),
   };
 
   let permissions = {
     let mut permissions =
       metadata.permissions.to_options(/* cli_arg_urls */ &[]);
-    // if running with an npm vfs, grant read access to it
-    if let Some(vfs_root) = maybe_vfs_root {
-      match &mut permissions.allow_read {
-        Some(vec) if vec.is_empty() => {
-          // do nothing, already granted
-        }
-        Some(vec) => {
-          vec.push(vfs_root.to_string_lossy().to_string());
-        }
-        None => {
-          permissions.allow_read =
-            Some(vec![vfs_root.to_string_lossy().to_string()]);
-        }
+    // grant read access to the vfs
+    match &mut permissions.allow_read {
+      Some(vec) if vec.is_empty() => {
+        // do nothing, already granted
+      }
+      Some(vec) => {
+        vec.push(root_path.to_string_lossy().to_string());
+      }
+      None => {
+        permissions.allow_read =
+          Some(vec![root_path.to_string_lossy().to_string()]);
       }
     }
 
@@ -706,6 +767,7 @@ pub async fn run(
     Box::new(module_loader_factory),
     node_resolver,
     npm_resolver,
+    pkg_json_resolver,
     root_cert_store_provider,
     permissions,
     StorageKeyResolver::empty(),
@@ -721,7 +783,6 @@ pub async fn run(
       inspect_wait: false,
       strace_ops: None,
       is_inspecting: false,
-      is_npm_main: main_module.scheme() == "npm",
       skip_op_registration: true,
       location: metadata.location,
       argv0: NpmPackageReqReference::from_specifier(&main_module)
diff --git a/cli/standalone/serialization.rs b/cli/standalone/serialization.rs
new file mode 100644
index 0000000000..a5eb649bfd
--- /dev/null
+++ b/cli/standalone/serialization.rs
@@ -0,0 +1,661 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::borrow::Cow;
+use std::collections::BTreeMap;
+use std::collections::HashMap;
+use std::io::Write;
+
+use deno_ast::MediaType;
+use deno_core::anyhow::bail;
+use deno_core::anyhow::Context;
+use deno_core::error::AnyError;
+use deno_core::serde_json;
+use deno_core::url::Url;
+use deno_core::FastString;
+use deno_core::ModuleSourceCode;
+use deno_core::ModuleType;
+use deno_npm::resolution::SerializedNpmResolutionSnapshot;
+use deno_npm::resolution::SerializedNpmResolutionSnapshotPackage;
+use deno_npm::resolution::ValidSerializedNpmResolutionSnapshot;
+use deno_npm::NpmPackageId;
+use deno_semver::package::PackageReq;
+
+use crate::standalone::virtual_fs::VirtualDirectory;
+
+use super::binary::Metadata;
+use super::virtual_fs::VfsBuilder;
+
+const MAGIC_BYTES: &[u8; 8] = b"d3n0l4nd";
+
+/// Binary format:
+/// * d3n0l4nd
+/// * <metadata_len><metadata>
+/// * <npm_snapshot_len><npm_snapshot>
+/// * <remote_modules_len><remote_modules>
+/// * <vfs_headers_len><vfs_headers>
+/// * <vfs_file_data_len><vfs_file_data>
+/// * d3n0l4nd
+pub fn serialize_binary_data_section(
+  metadata: &Metadata,
+  npm_snapshot: Option<SerializedNpmResolutionSnapshot>,
+  remote_modules: &RemoteModulesStoreBuilder,
+  vfs: VfsBuilder,
+) -> Result<Vec<u8>, AnyError> {
+  fn write_bytes_with_len(bytes: &mut Vec<u8>, data: &[u8]) {
+    bytes.extend_from_slice(&(data.len() as u64).to_le_bytes());
+    bytes.extend_from_slice(data);
+  }
+
+  let mut bytes = Vec::new();
+  bytes.extend_from_slice(MAGIC_BYTES);
+
+  // 1. Metadata
+  {
+    let metadata = serde_json::to_string(metadata)?;
+    write_bytes_with_len(&mut bytes, metadata.as_bytes());
+  }
+  // 2. Npm snapshot
+  {
+    let npm_snapshot =
+      npm_snapshot.map(serialize_npm_snapshot).unwrap_or_default();
+    write_bytes_with_len(&mut bytes, &npm_snapshot);
+  }
+  // 3. Remote modules
+  {
+    let update_index = bytes.len();
+    bytes.extend_from_slice(&(0_u64).to_le_bytes());
+    let start_index = bytes.len();
+    remote_modules.write(&mut bytes)?;
+    let length = bytes.len() - start_index;
+    let length_bytes = (length as u64).to_le_bytes();
+    bytes[update_index..update_index + length_bytes.len()]
+      .copy_from_slice(&length_bytes);
+  }
+  // 4. VFS
+  {
+    let (vfs, vfs_files) = vfs.into_dir_and_files();
+    let vfs = serde_json::to_string(&vfs)?;
+    write_bytes_with_len(&mut bytes, vfs.as_bytes());
+    let vfs_bytes_len = vfs_files.iter().map(|f| f.len() as u64).sum::<u64>();
+    bytes.extend_from_slice(&vfs_bytes_len.to_le_bytes());
+    for file in &vfs_files {
+      bytes.extend_from_slice(file);
+    }
+  }
+
+  // write the magic bytes at the end so we can use it
+  // to make sure we've deserialized correctly
+  bytes.extend_from_slice(MAGIC_BYTES);
+
+  Ok(bytes)
+}
+
+pub struct DeserializedDataSection {
+  pub metadata: Metadata,
+  pub npm_snapshot: Option<ValidSerializedNpmResolutionSnapshot>,
+  pub remote_modules: RemoteModulesStore,
+  pub vfs_dir: VirtualDirectory,
+  pub vfs_files_data: &'static [u8],
+}
+
+pub fn deserialize_binary_data_section(
+  data: &'static [u8],
+) -> Result<Option<DeserializedDataSection>, AnyError> {
+  fn read_bytes_with_len(input: &[u8]) -> Result<(&[u8], &[u8]), AnyError> {
+    let (input, len) = read_u64(input)?;
+    let (input, data) = read_bytes(input, len as usize)?;
+    Ok((input, data))
+  }
+
+  fn read_magic_bytes(input: &[u8]) -> Result<(&[u8], bool), AnyError> {
+    if input.len() < MAGIC_BYTES.len() {
+      bail!("Unexpected end of data. Could not find magic bytes.");
+    }
+    let (magic_bytes, input) = input.split_at(MAGIC_BYTES.len());
+    if magic_bytes != MAGIC_BYTES {
+      return Ok((input, false));
+    }
+    Ok((input, true))
+  }
+
+  let (input, found) = read_magic_bytes(data)?;
+  if !found {
+    return Ok(None);
+  }
+
+  // 1. Metadata
+  let (input, data) = read_bytes_with_len(input).context("reading metadata")?;
+  let metadata: Metadata =
+    serde_json::from_slice(data).context("deserializing metadata")?;
+  // 2. Npm snapshot
+  let (input, data) =
+    read_bytes_with_len(input).context("reading npm snapshot")?;
+  let npm_snapshot = if data.is_empty() {
+    None
+  } else {
+    Some(deserialize_npm_snapshot(data).context("deserializing npm snapshot")?)
+  };
+  // 3. Remote modules
+  let (input, data) =
+    read_bytes_with_len(input).context("reading remote modules data")?;
+  let remote_modules =
+    RemoteModulesStore::build(data).context("deserializing remote modules")?;
+  // 4. VFS
+  let (input, data) = read_bytes_with_len(input).context("vfs")?;
+  let vfs_dir: VirtualDirectory =
+    serde_json::from_slice(data).context("deserializing vfs data")?;
+  let (input, vfs_files_data) =
+    read_bytes_with_len(input).context("reading vfs files data")?;
+
+  // finally ensure we read the magic bytes at the end
+  let (_input, found) = read_magic_bytes(input)?;
+  if !found {
+    bail!("Could not find magic bytes at the end of the data.");
+  }
+
+  Ok(Some(DeserializedDataSection {
+    metadata,
+    npm_snapshot,
+    remote_modules,
+    vfs_dir,
+    vfs_files_data,
+  }))
+}
+
+#[derive(Default)]
+pub struct RemoteModulesStoreBuilder {
+  specifiers: Vec<(String, u64)>,
+  data: Vec<(MediaType, Vec<u8>)>,
+  data_byte_len: u64,
+  redirects: Vec<(String, String)>,
+  redirects_len: u64,
+}
+
+impl RemoteModulesStoreBuilder {
+  pub fn add(&mut self, specifier: &Url, media_type: MediaType, data: Vec<u8>) {
+    log::debug!("Adding '{}' ({})", specifier, media_type);
+    let specifier = specifier.to_string();
+    self.specifiers.push((specifier, self.data_byte_len));
+    self.data_byte_len += 1 + 8 + data.len() as u64; // media type (1 byte), data length (8 bytes), data
+    self.data.push((media_type, data));
+  }
+
+  pub fn add_redirects(&mut self, redirects: &BTreeMap<Url, Url>) {
+    self.redirects.reserve(redirects.len());
+    for (from, to) in redirects {
+      log::debug!("Adding redirect '{}' -> '{}'", from, to);
+      let from = from.to_string();
+      let to = to.to_string();
+      self.redirects_len += (4 + from.len() + 4 + to.len()) as u64;
+      self.redirects.push((from, to));
+    }
+  }
+
+  fn write(&self, writer: &mut dyn Write) -> Result<(), AnyError> {
+    writer.write_all(&(self.specifiers.len() as u32).to_le_bytes())?;
+    writer.write_all(&(self.redirects.len() as u32).to_le_bytes())?;
+    for (specifier, offset) in &self.specifiers {
+      writer.write_all(&(specifier.len() as u32).to_le_bytes())?;
+      writer.write_all(specifier.as_bytes())?;
+      writer.write_all(&offset.to_le_bytes())?;
+    }
+    for (from, to) in &self.redirects {
+      writer.write_all(&(from.len() as u32).to_le_bytes())?;
+      writer.write_all(from.as_bytes())?;
+      writer.write_all(&(to.len() as u32).to_le_bytes())?;
+      writer.write_all(to.as_bytes())?;
+    }
+    for (media_type, data) in &self.data {
+      writer.write_all(&[serialize_media_type(*media_type)])?;
+      writer.write_all(&(data.len() as u64).to_le_bytes())?;
+      writer.write_all(data)?;
+    }
+    Ok(())
+  }
+}
+
+pub enum DenoCompileModuleSource {
+  String(&'static str),
+  Bytes(Cow<'static, [u8]>),
+}
+
+impl DenoCompileModuleSource {
+  pub fn into_for_v8(self) -> ModuleSourceCode {
+    fn into_bytes(data: Cow<'static, [u8]>) -> ModuleSourceCode {
+      ModuleSourceCode::Bytes(match data {
+        Cow::Borrowed(d) => d.into(),
+        Cow::Owned(d) => d.into_boxed_slice().into(),
+      })
+    }
+
+    match self {
+      // todo(https://github.com/denoland/deno_core/pull/943): store whether
+      // the string is ascii or not ahead of time so we can avoid the is_ascii()
+      // check in FastString::from_static
+      Self::String(s) => ModuleSourceCode::String(FastString::from_static(s)),
+      Self::Bytes(b) => into_bytes(b),
+    }
+  }
+}
+
+pub struct DenoCompileModuleData<'a> {
+  pub specifier: &'a Url,
+  pub media_type: MediaType,
+  pub data: Cow<'static, [u8]>,
+}
+
+impl<'a> DenoCompileModuleData<'a> {
+  pub fn into_parts(self) -> (&'a Url, ModuleType, DenoCompileModuleSource) {
+    fn into_string_unsafe(data: Cow<'static, [u8]>) -> DenoCompileModuleSource {
+      match data {
+        Cow::Borrowed(d) => DenoCompileModuleSource::String(
+          // SAFETY: we know this is a valid utf8 string
+          unsafe { std::str::from_utf8_unchecked(d) },
+        ),
+        Cow::Owned(d) => DenoCompileModuleSource::Bytes(Cow::Owned(d)),
+      }
+    }
+
+    let (media_type, source) = match self.media_type {
+      MediaType::JavaScript
+      | MediaType::Jsx
+      | MediaType::Mjs
+      | MediaType::Cjs
+      | MediaType::TypeScript
+      | MediaType::Mts
+      | MediaType::Cts
+      | MediaType::Dts
+      | MediaType::Dmts
+      | MediaType::Dcts
+      | MediaType::Tsx => {
+        (ModuleType::JavaScript, into_string_unsafe(self.data))
+      }
+      MediaType::Json => (ModuleType::Json, into_string_unsafe(self.data)),
+      MediaType::Wasm => {
+        (ModuleType::Wasm, DenoCompileModuleSource::Bytes(self.data))
+      }
+      // just assume javascript if we made it here
+      MediaType::Css | MediaType::SourceMap | MediaType::Unknown => (
+        ModuleType::JavaScript,
+        DenoCompileModuleSource::Bytes(self.data),
+      ),
+    };
+    (self.specifier, media_type, source)
+  }
+}
+
+enum RemoteModulesStoreSpecifierValue {
+  Data(usize),
+  Redirect(Url),
+}
+
+pub struct RemoteModulesStore {
+  specifiers: HashMap<Url, RemoteModulesStoreSpecifierValue>,
+  files_data: &'static [u8],
+}
+
+impl RemoteModulesStore {
+  fn build(data: &'static [u8]) -> Result<Self, AnyError> {
+    fn read_specifier(input: &[u8]) -> Result<(&[u8], (Url, u64)), AnyError> {
+      let (input, specifier) = read_string_lossy(input)?;
+      let specifier = Url::parse(&specifier)?;
+      let (input, offset) = read_u64(input)?;
+      Ok((input, (specifier, offset)))
+    }
+
+    fn read_redirect(input: &[u8]) -> Result<(&[u8], (Url, Url)), AnyError> {
+      let (input, from) = read_string_lossy(input)?;
+      let from = Url::parse(&from)?;
+      let (input, to) = read_string_lossy(input)?;
+      let to = Url::parse(&to)?;
+      Ok((input, (from, to)))
+    }
+
+    fn read_headers(
+      input: &[u8],
+    ) -> Result<(&[u8], HashMap<Url, RemoteModulesStoreSpecifierValue>), AnyError>
+    {
+      let (input, specifiers_len) = read_u32_as_usize(input)?;
+      let (mut input, redirects_len) = read_u32_as_usize(input)?;
+      let mut specifiers =
+        HashMap::with_capacity(specifiers_len + redirects_len);
+      for _ in 0..specifiers_len {
+        let (current_input, (specifier, offset)) =
+          read_specifier(input).context("reading specifier")?;
+        input = current_input;
+        specifiers.insert(
+          specifier,
+          RemoteModulesStoreSpecifierValue::Data(offset as usize),
+        );
+      }
+
+      for _ in 0..redirects_len {
+        let (current_input, (from, to)) = read_redirect(input)?;
+        input = current_input;
+        specifiers.insert(from, RemoteModulesStoreSpecifierValue::Redirect(to));
+      }
+
+      Ok((input, specifiers))
+    }
+
+    let (files_data, specifiers) = read_headers(data)?;
+
+    Ok(Self {
+      specifiers,
+      files_data,
+    })
+  }
+
+  pub fn resolve_specifier<'a>(
+    &'a self,
+    specifier: &'a Url,
+  ) -> Result<Option<&'a Url>, AnyError> {
+    let mut count = 0;
+    let mut current = specifier;
+    loop {
+      if count > 10 {
+        bail!("Too many redirects resolving '{}'", specifier);
+      }
+      match self.specifiers.get(current) {
+        Some(RemoteModulesStoreSpecifierValue::Redirect(to)) => {
+          current = to;
+          count += 1;
+        }
+        Some(RemoteModulesStoreSpecifierValue::Data(_)) => {
+          return Ok(Some(current));
+        }
+        None => {
+          return Ok(None);
+        }
+      }
+    }
+  }
+
+  pub fn read<'a>(
+    &'a self,
+    original_specifier: &'a Url,
+  ) -> Result<Option<DenoCompileModuleData<'a>>, AnyError> {
+    let mut count = 0;
+    let mut specifier = original_specifier;
+    loop {
+      if count > 10 {
+        bail!("Too many redirects resolving '{}'", original_specifier);
+      }
+      match self.specifiers.get(specifier) {
+        Some(RemoteModulesStoreSpecifierValue::Redirect(to)) => {
+          specifier = to;
+          count += 1;
+        }
+        Some(RemoteModulesStoreSpecifierValue::Data(offset)) => {
+          let input = &self.files_data[*offset..];
+          let (input, media_type_byte) = read_bytes(input, 1)?;
+          let media_type = deserialize_media_type(media_type_byte[0])?;
+          let (input, len) = read_u64(input)?;
+          let (_input, data) = read_bytes(input, len as usize)?;
+          return Ok(Some(DenoCompileModuleData {
+            specifier,
+            media_type,
+            data: Cow::Borrowed(data),
+          }));
+        }
+        None => {
+          return Ok(None);
+        }
+      }
+    }
+  }
+}
+
+fn serialize_npm_snapshot(
+  mut snapshot: SerializedNpmResolutionSnapshot,
+) -> Vec<u8> {
+  fn append_string(bytes: &mut Vec<u8>, string: &str) {
+    let len = string.len() as u32;
+    bytes.extend_from_slice(&len.to_le_bytes());
+    bytes.extend_from_slice(string.as_bytes());
+  }
+
+  snapshot.packages.sort_by(|a, b| a.id.cmp(&b.id)); // determinism
+  let ids_to_stored_ids = snapshot
+    .packages
+    .iter()
+    .enumerate()
+    .map(|(i, pkg)| (&pkg.id, i as u32))
+    .collect::<HashMap<_, _>>();
+
+  let mut root_packages: Vec<_> = snapshot.root_packages.iter().collect();
+  root_packages.sort();
+  let mut bytes = Vec::new();
+
+  bytes.extend_from_slice(&(snapshot.packages.len() as u32).to_le_bytes());
+  for pkg in &snapshot.packages {
+    append_string(&mut bytes, &pkg.id.as_serialized());
+  }
+
+  bytes.extend_from_slice(&(root_packages.len() as u32).to_le_bytes());
+  for (req, id) in root_packages {
+    append_string(&mut bytes, &req.to_string());
+    let id = ids_to_stored_ids.get(&id).unwrap();
+    bytes.extend_from_slice(&id.to_le_bytes());
+  }
+
+  for pkg in &snapshot.packages {
+    let deps_len = pkg.dependencies.len() as u32;
+    bytes.extend_from_slice(&deps_len.to_le_bytes());
+    let mut deps: Vec<_> = pkg.dependencies.iter().collect();
+    deps.sort();
+    for (req, id) in deps {
+      append_string(&mut bytes, req);
+      let id = ids_to_stored_ids.get(&id).unwrap();
+      bytes.extend_from_slice(&id.to_le_bytes());
+    }
+  }
+
+  bytes
+}
+
+fn deserialize_npm_snapshot(
+  input: &[u8],
+) -> Result<ValidSerializedNpmResolutionSnapshot, AnyError> {
+  fn parse_id(input: &[u8]) -> Result<(&[u8], NpmPackageId), AnyError> {
+    let (input, id) = read_string_lossy(input)?;
+    let id = NpmPackageId::from_serialized(&id)?;
+    Ok((input, id))
+  }
+
+  #[allow(clippy::needless_lifetimes)] // clippy bug
+  fn parse_root_package<'a>(
+    id_to_npm_id: &'a impl Fn(usize) -> Result<NpmPackageId, AnyError>,
+  ) -> impl Fn(&[u8]) -> Result<(&[u8], (PackageReq, NpmPackageId)), AnyError> + 'a
+  {
+    |input| {
+      let (input, req) = read_string_lossy(input)?;
+      let req = PackageReq::from_str(&req)?;
+      let (input, id) = read_u32_as_usize(input)?;
+      Ok((input, (req, id_to_npm_id(id)?)))
+    }
+  }
+
+  #[allow(clippy::needless_lifetimes)] // clippy bug
+  fn parse_package_dep<'a>(
+    id_to_npm_id: &'a impl Fn(usize) -> Result<NpmPackageId, AnyError>,
+  ) -> impl Fn(&[u8]) -> Result<(&[u8], (String, NpmPackageId)), AnyError> + 'a
+  {
+    |input| {
+      let (input, req) = read_string_lossy(input)?;
+      let (input, id) = read_u32_as_usize(input)?;
+      Ok((input, (req.into_owned(), id_to_npm_id(id)?)))
+    }
+  }
+
+  fn parse_package<'a>(
+    input: &'a [u8],
+    id: NpmPackageId,
+    id_to_npm_id: &impl Fn(usize) -> Result<NpmPackageId, AnyError>,
+  ) -> Result<(&'a [u8], SerializedNpmResolutionSnapshotPackage), AnyError> {
+    let (input, deps_len) = read_u32_as_usize(input)?;
+    let (input, dependencies) =
+      parse_hashmap_n_times(input, deps_len, parse_package_dep(id_to_npm_id))?;
+    Ok((
+      input,
+      SerializedNpmResolutionSnapshotPackage {
+        id,
+        system: Default::default(),
+        dist: Default::default(),
+        dependencies,
+        optional_dependencies: Default::default(),
+        bin: None,
+        scripts: Default::default(),
+        deprecated: Default::default(),
+      },
+    ))
+  }
+
+  let (input, packages_len) = read_u32_as_usize(input)?;
+
+  // get a hashmap of all the npm package ids to their serialized ids
+  let (input, data_ids_to_npm_ids) =
+    parse_vec_n_times(input, packages_len, parse_id)
+      .context("deserializing id")?;
+  let data_id_to_npm_id = |id: usize| {
+    data_ids_to_npm_ids
+      .get(id)
+      .cloned()
+      .ok_or_else(|| deno_core::anyhow::anyhow!("Invalid npm package id"))
+  };
+
+  let (input, root_packages_len) = read_u32_as_usize(input)?;
+  let (input, root_packages) = parse_hashmap_n_times(
+    input,
+    root_packages_len,
+    parse_root_package(&data_id_to_npm_id),
+  )
+  .context("deserializing root package")?;
+  let (input, packages) =
+    parse_vec_n_times_with_index(input, packages_len, |input, index| {
+      parse_package(input, data_id_to_npm_id(index)?, &data_id_to_npm_id)
+    })
+    .context("deserializing package")?;
+
+  if !input.is_empty() {
+    bail!("Unexpected data left over");
+  }
+
+  Ok(
+    SerializedNpmResolutionSnapshot {
+      packages,
+      root_packages,
+    }
+    // this is ok because we have already verified that all the
+    // identifiers found in the snapshot are valid via the
+    // npm package id -> npm package id mapping
+    .into_valid_unsafe(),
+  )
+}
+
+fn serialize_media_type(media_type: MediaType) -> u8 {
+  match media_type {
+    MediaType::JavaScript => 0,
+    MediaType::Jsx => 1,
+    MediaType::Mjs => 2,
+    MediaType::Cjs => 3,
+    MediaType::TypeScript => 4,
+    MediaType::Mts => 5,
+    MediaType::Cts => 6,
+    MediaType::Dts => 7,
+    MediaType::Dmts => 8,
+    MediaType::Dcts => 9,
+    MediaType::Tsx => 10,
+    MediaType::Json => 11,
+    MediaType::Wasm => 12,
+    MediaType::Css => 13,
+    MediaType::SourceMap => 14,
+    MediaType::Unknown => 15,
+  }
+}
+
+fn deserialize_media_type(value: u8) -> Result<MediaType, AnyError> {
+  match value {
+    0 => Ok(MediaType::JavaScript),
+    1 => Ok(MediaType::Jsx),
+    2 => Ok(MediaType::Mjs),
+    3 => Ok(MediaType::Cjs),
+    4 => Ok(MediaType::TypeScript),
+    5 => Ok(MediaType::Mts),
+    6 => Ok(MediaType::Cts),
+    7 => Ok(MediaType::Dts),
+    8 => Ok(MediaType::Dmts),
+    9 => Ok(MediaType::Dcts),
+    10 => Ok(MediaType::Tsx),
+    11 => Ok(MediaType::Json),
+    12 => Ok(MediaType::Wasm),
+    13 => Ok(MediaType::Css),
+    14 => Ok(MediaType::SourceMap),
+    15 => Ok(MediaType::Unknown),
+    _ => bail!("Unknown media type value: {}", value),
+  }
+}
+
+fn parse_hashmap_n_times<TKey: std::cmp::Eq + std::hash::Hash, TValue>(
+  mut input: &[u8],
+  times: usize,
+  parse: impl Fn(&[u8]) -> Result<(&[u8], (TKey, TValue)), AnyError>,
+) -> Result<(&[u8], HashMap<TKey, TValue>), AnyError> {
+  let mut results = HashMap::with_capacity(times);
+  for _ in 0..times {
+    let result = parse(input);
+    let (new_input, (key, value)) = result?;
+    results.insert(key, value);
+    input = new_input;
+  }
+  Ok((input, results))
+}
+
+fn parse_vec_n_times<TResult>(
+  input: &[u8],
+  times: usize,
+  parse: impl Fn(&[u8]) -> Result<(&[u8], TResult), AnyError>,
+) -> Result<(&[u8], Vec<TResult>), AnyError> {
+  parse_vec_n_times_with_index(input, times, |input, _index| parse(input))
+}
+
+fn parse_vec_n_times_with_index<TResult>(
+  mut input: &[u8],
+  times: usize,
+  parse: impl Fn(&[u8], usize) -> Result<(&[u8], TResult), AnyError>,
+) -> Result<(&[u8], Vec<TResult>), AnyError> {
+  let mut results = Vec::with_capacity(times);
+  for i in 0..times {
+    let result = parse(input, i);
+    let (new_input, result) = result?;
+    results.push(result);
+    input = new_input;
+  }
+  Ok((input, results))
+}
+
+fn read_bytes(input: &[u8], len: usize) -> Result<(&[u8], &[u8]), AnyError> {
+  if input.len() < len {
+    bail!("Unexpected end of data.",);
+  }
+  let (len_bytes, input) = input.split_at(len);
+  Ok((input, len_bytes))
+}
+
+fn read_string_lossy(input: &[u8]) -> Result<(&[u8], Cow<str>), AnyError> {
+  let (input, str_len) = read_u32_as_usize(input)?;
+  let (input, data_bytes) = read_bytes(input, str_len)?;
+  Ok((input, String::from_utf8_lossy(data_bytes)))
+}
+
+fn read_u32_as_usize(input: &[u8]) -> Result<(&[u8], usize), AnyError> {
+  let (input, len_bytes) = read_bytes(input, 4)?;
+  let len = u32::from_le_bytes(len_bytes.try_into()?);
+  Ok((input, len as usize))
+}
+
+fn read_u64(input: &[u8]) -> Result<(&[u8], u64), AnyError> {
+  let (input, len_bytes) = read_bytes(input, 8)?;
+  let len = u64::from_le_bytes(len_bytes.try_into()?);
+  Ok((input, len))
+}
diff --git a/cli/standalone/virtual_fs.rs b/cli/standalone/virtual_fs.rs
index 53d045b625..0ae00accbf 100644
--- a/cli/standalone/virtual_fs.rs
+++ b/cli/standalone/virtual_fs.rs
@@ -7,6 +7,7 @@ use std::fs::File;
 use std::io::Read;
 use std::io::Seek;
 use std::io::SeekFrom;
+use std::ops::Range;
 use std::path::Path;
 use std::path::PathBuf;
 use std::rc::Rc;
@@ -67,6 +68,26 @@ impl VfsBuilder {
     })
   }
 
+  pub fn set_new_root_path(
+    &mut self,
+    root_path: PathBuf,
+  ) -> Result<(), AnyError> {
+    let root_path = canonicalize_path(&root_path)?;
+    self.root_path = root_path;
+    self.root_dir = VirtualDirectory {
+      name: self
+        .root_path
+        .file_stem()
+        .map(|s| s.to_string_lossy().into_owned())
+        .unwrap_or("root".to_string()),
+      entries: vec![VfsEntry::Dir(VirtualDirectory {
+        name: std::mem::take(&mut self.root_dir.name),
+        entries: std::mem::take(&mut self.root_dir.entries),
+      })],
+    };
+    Ok(())
+  }
+
   pub fn with_root_dir<R>(
     &mut self,
     with_root: impl FnOnce(&mut VirtualDirectory) -> R,
@@ -119,7 +140,7 @@ impl VfsBuilder {
                 // inline the symlink and make the target file
                 let file_bytes = std::fs::read(&target)
                   .with_context(|| format!("Reading {}", path.display()))?;
-                self.add_file(&path, file_bytes)?;
+                self.add_file_with_data_inner(&path, file_bytes)?;
               } else {
                 log::warn!(
                   "{} Symlink target is outside '{}'. Excluding symlink at '{}' with target '{}'.",
@@ -191,16 +212,32 @@ impl VfsBuilder {
     self.add_file_at_path_not_symlink(&target_path)
   }
 
-  pub fn add_file_at_path_not_symlink(
+  fn add_file_at_path_not_symlink(
     &mut self,
     path: &Path,
   ) -> Result<(), AnyError> {
     let file_bytes = std::fs::read(path)
       .with_context(|| format!("Reading {}", path.display()))?;
-    self.add_file(path, file_bytes)
+    self.add_file_with_data_inner(path, file_bytes)
   }
 
-  fn add_file(&mut self, path: &Path, data: Vec<u8>) -> Result<(), AnyError> {
+  pub fn add_file_with_data(
+    &mut self,
+    path: &Path,
+    data: Vec<u8>,
+  ) -> Result<(), AnyError> {
+    let target_path = canonicalize_path(path)?;
+    if target_path != path {
+      self.add_symlink(path, &target_path)?;
+    }
+    self.add_file_with_data_inner(&target_path, data)
+  }
+
+  fn add_file_with_data_inner(
+    &mut self,
+    path: &Path,
+    data: Vec<u8>,
+  ) -> Result<(), AnyError> {
     log::debug!("Adding file '{}'", path.display());
     let checksum = util::checksum::gen(&[&data]);
     let offset = if let Some(offset) = self.file_offsets.get(&checksum) {
@@ -249,8 +286,15 @@ impl VfsBuilder {
       path.display(),
       target.display()
     );
-    let dest = self.path_relative_root(target)?;
-    if dest == self.path_relative_root(path)? {
+    let relative_target = self.path_relative_root(target)?;
+    let relative_path = match self.path_relative_root(path) {
+      Ok(path) => path,
+      Err(StripRootError { .. }) => {
+        // ignore if the original path is outside the root directory
+        return Ok(());
+      }
+    };
+    if relative_target == relative_path {
       // it's the same, ignore
       return Ok(());
     }
@@ -263,7 +307,7 @@ impl VfsBuilder {
           insert_index,
           VfsEntry::Symlink(VirtualSymlink {
             name: name.to_string(),
-            dest_parts: dest
+            dest_parts: relative_target
               .components()
               .map(|c| c.as_os_str().to_string_lossy().to_string())
               .collect::<Vec<_>>(),
@@ -751,14 +795,14 @@ impl deno_io::fs::File for FileBackedVfsFile {
 
 #[derive(Debug)]
 pub struct FileBackedVfs {
-  file: Mutex<Vec<u8>>,
+  vfs_data: Cow<'static, [u8]>,
   fs_root: VfsRoot,
 }
 
 impl FileBackedVfs {
-  pub fn new(file: Vec<u8>, fs_root: VfsRoot) -> Self {
+  pub fn new(data: Cow<'static, [u8]>, fs_root: VfsRoot) -> Self {
     Self {
-      file: Mutex::new(file),
+      vfs_data: data,
       fs_root,
     }
   }
@@ -827,10 +871,15 @@ impl FileBackedVfs {
     Ok(path)
   }
 
-  pub fn read_file_all(&self, file: &VirtualFile) -> std::io::Result<Vec<u8>> {
-    let mut buf = vec![0; file.len as usize];
-    self.read_file(file, 0, &mut buf)?;
-    Ok(buf)
+  pub fn read_file_all(
+    &self,
+    file: &VirtualFile,
+  ) -> std::io::Result<Cow<'static, [u8]>> {
+    let read_range = self.get_read_range(file, 0, file.len)?;
+    match &self.vfs_data {
+      Cow::Borrowed(data) => Ok(Cow::Borrowed(&data[read_range])),
+      Cow::Owned(data) => Ok(Cow::Owned(data[read_range].to_vec())),
+    }
   }
 
   pub fn read_file(
@@ -839,18 +888,27 @@ impl FileBackedVfs {
     pos: u64,
     buf: &mut [u8],
   ) -> std::io::Result<usize> {
-    let data = self.file.lock();
+    let read_range = self.get_read_range(file, pos, buf.len() as u64)?;
+    buf.copy_from_slice(&self.vfs_data[read_range]);
+    Ok(buf.len())
+  }
+
+  fn get_read_range(
+    &self,
+    file: &VirtualFile,
+    pos: u64,
+    len: u64,
+  ) -> std::io::Result<Range<usize>> {
+    let data = &self.vfs_data;
     let start = self.fs_root.start_file_offset + file.offset + pos;
-    let end = start + buf.len() as u64;
+    let end = start + len;
     if end > data.len() as u64 {
       return Err(std::io::Error::new(
         std::io::ErrorKind::UnexpectedEof,
         "unexpected EOF",
       ));
     }
-
-    buf.copy_from_slice(&data[start as usize..end as usize]);
-    Ok(buf.len())
+    Ok(start as usize..end as usize)
   }
 
   pub fn dir_entry(&self, path: &Path) -> std::io::Result<&VirtualDirectory> {
@@ -888,7 +946,7 @@ mod test {
   #[track_caller]
   fn read_file(vfs: &FileBackedVfs, path: &Path) -> String {
     let file = vfs.file_entry(path).unwrap();
-    String::from_utf8(vfs.read_file_all(file).unwrap()).unwrap()
+    String::from_utf8(vfs.read_file_all(file).unwrap().into_owned()).unwrap()
   }
 
   #[test]
@@ -901,20 +959,23 @@ mod test {
     let src_path = src_path.to_path_buf();
     let mut builder = VfsBuilder::new(src_path.clone()).unwrap();
     builder
-      .add_file(&src_path.join("a.txt"), "data".into())
+      .add_file_with_data_inner(&src_path.join("a.txt"), "data".into())
       .unwrap();
     builder
-      .add_file(&src_path.join("b.txt"), "data".into())
+      .add_file_with_data_inner(&src_path.join("b.txt"), "data".into())
       .unwrap();
     assert_eq!(builder.files.len(), 1); // because duplicate data
     builder
-      .add_file(&src_path.join("c.txt"), "c".into())
+      .add_file_with_data_inner(&src_path.join("c.txt"), "c".into())
       .unwrap();
     builder
-      .add_file(&src_path.join("sub_dir").join("d.txt"), "d".into())
+      .add_file_with_data_inner(
+        &src_path.join("sub_dir").join("d.txt"),
+        "d".into(),
+      )
       .unwrap();
     builder
-      .add_file(&src_path.join("e.txt"), "e".into())
+      .add_file_with_data_inner(&src_path.join("e.txt"), "e".into())
       .unwrap();
     builder
       .add_symlink(
@@ -1031,7 +1092,7 @@ mod test {
     (
       dest_path.to_path_buf(),
       FileBackedVfs::new(
-        data,
+        Cow::Owned(data),
         VfsRoot {
           dir: root_dir,
           root_path: dest_path.to_path_buf(),
@@ -1082,7 +1143,7 @@ mod test {
     let temp_path = temp_dir.path().canonicalize();
     let mut builder = VfsBuilder::new(temp_path.to_path_buf()).unwrap();
     builder
-      .add_file(
+      .add_file_with_data_inner(
         temp_path.join("a.txt").as_path(),
         "0123456789".to_string().into_bytes(),
       )
diff --git a/cli/task_runner.rs b/cli/task_runner.rs
index ab7163bc93..43840e868d 100644
--- a/cli/task_runner.rs
+++ b/cli/task_runner.rs
@@ -16,8 +16,11 @@ use deno_task_shell::ExecutableCommand;
 use deno_task_shell::ExecuteResult;
 use deno_task_shell::ShellCommand;
 use deno_task_shell::ShellCommandContext;
+use deno_task_shell::ShellPipeReader;
+use deno_task_shell::ShellPipeWriter;
 use lazy_regex::Lazy;
 use regex::Regex;
+use tokio::task::JoinHandle;
 use tokio::task::LocalSet;
 
 use crate::npm::CliNpmResolver;
@@ -36,6 +39,35 @@ pub fn get_script_with_args(script: &str, argv: &[String]) -> String {
   script.trim().to_owned()
 }
 
+pub struct TaskStdio(Option<ShellPipeReader>, ShellPipeWriter);
+
+impl TaskStdio {
+  pub fn stdout() -> Self {
+    Self(None, ShellPipeWriter::stdout())
+  }
+  pub fn stderr() -> Self {
+    Self(None, ShellPipeWriter::stderr())
+  }
+  pub fn piped() -> Self {
+    let (r, w) = deno_task_shell::pipe();
+    Self(Some(r), w)
+  }
+}
+
+pub struct TaskIo {
+  pub stdout: TaskStdio,
+  pub stderr: TaskStdio,
+}
+
+impl Default for TaskIo {
+  fn default() -> Self {
+    Self {
+      stderr: TaskStdio::stderr(),
+      stdout: TaskStdio::stdout(),
+    }
+  }
+}
+
 pub struct RunTaskOptions<'a> {
   pub task_name: &'a str,
   pub script: &'a str,
@@ -45,24 +77,69 @@ pub struct RunTaskOptions<'a> {
   pub argv: &'a [String],
   pub custom_commands: HashMap<String, Rc<dyn ShellCommand>>,
   pub root_node_modules_dir: Option<&'a Path>,
+  pub stdio: Option<TaskIo>,
 }
 
 pub type TaskCustomCommands = HashMap<String, Rc<dyn ShellCommand>>;
 
-pub async fn run_task(opts: RunTaskOptions<'_>) -> Result<i32, AnyError> {
+pub struct TaskResult {
+  pub exit_code: i32,
+  pub stdout: Option<Vec<u8>>,
+  pub stderr: Option<Vec<u8>>,
+}
+
+pub async fn run_task(
+  opts: RunTaskOptions<'_>,
+) -> Result<TaskResult, AnyError> {
   let script = get_script_with_args(opts.script, opts.argv);
   let seq_list = deno_task_shell::parser::parse(&script)
     .with_context(|| format!("Error parsing script '{}'.", opts.task_name))?;
   let env_vars =
     prepare_env_vars(opts.env_vars, opts.init_cwd, opts.root_node_modules_dir);
+  let state =
+    deno_task_shell::ShellState::new(env_vars, opts.cwd, opts.custom_commands);
+  let stdio = opts.stdio.unwrap_or_default();
+  let (
+    TaskStdio(stdout_read, stdout_write),
+    TaskStdio(stderr_read, stderr_write),
+  ) = (stdio.stdout, stdio.stderr);
+
+  fn read(reader: ShellPipeReader) -> JoinHandle<Result<Vec<u8>, AnyError>> {
+    tokio::task::spawn_blocking(move || {
+      let mut buf = Vec::new();
+      reader.pipe_to(&mut buf)?;
+      Ok(buf)
+    })
+  }
+
+  let stdout = stdout_read.map(read);
+  let stderr = stderr_read.map(read);
+
   let local = LocalSet::new();
-  let future = deno_task_shell::execute(
-    seq_list,
-    env_vars,
-    opts.cwd,
-    opts.custom_commands,
-  );
-  Ok(local.run_until(future).await)
+  let future = async move {
+    let exit_code = deno_task_shell::execute_with_pipes(
+      seq_list,
+      state,
+      ShellPipeReader::stdin(),
+      stdout_write,
+      stderr_write,
+    )
+    .await;
+    Ok::<_, AnyError>(TaskResult {
+      exit_code,
+      stdout: if let Some(stdout) = stdout {
+        Some(stdout.await??)
+      } else {
+        None
+      },
+      stderr: if let Some(stderr) = stderr {
+        Some(stderr.await??)
+      } else {
+        None
+      },
+    })
+  };
+  local.run_until(future).await
 }
 
 fn prepare_env_vars(
@@ -78,6 +155,12 @@ fn prepare_env_vars(
       initial_cwd.to_string_lossy().to_string(),
     );
   }
+  if !env_vars.contains_key(crate::npm::NPM_CONFIG_USER_AGENT_ENV_VAR) {
+    env_vars.insert(
+      crate::npm::NPM_CONFIG_USER_AGENT_ENV_VAR.into(),
+      crate::npm::get_npm_config_user_agent(),
+    );
+  }
   if let Some(node_modules_dir) = node_modules_dir {
     prepend_to_path(
       &mut env_vars,
@@ -127,7 +210,7 @@ impl ShellCommand for NpmCommand {
     mut context: ShellCommandContext,
   ) -> LocalBoxFuture<'static, ExecuteResult> {
     if context.args.first().map(|s| s.as_str()) == Some("run")
-      && context.args.len() > 2
+      && context.args.len() >= 2
       // for now, don't run any npm scripts that have a flag because
       // we don't handle stuff like `--workspaces` properly
       && !context.args.iter().any(|s| s.starts_with('-'))
@@ -190,10 +273,12 @@ impl ShellCommand for NodeCommand {
       )
       .execute(context);
     }
+
     args.extend(["run", "-A"].into_iter().map(|s| s.to_string()));
     args.extend(context.args.iter().cloned());
 
     let mut state = context.state;
+
     state.apply_env_var(USE_PKG_JSON_HIDDEN_ENV_VAR_NAME, "1");
     ExecutableCommand::new("deno".to_string(), std::env::current_exe().unwrap())
       .execute(ShellCommandContext {
diff --git a/cli/tools/bench/mod.rs b/cli/tools/bench/mod.rs
index be5d0ad0e1..272d063355 100644
--- a/cli/tools/bench/mod.rs
+++ b/cli/tools/bench/mod.rs
@@ -193,7 +193,7 @@ async fn bench_specifier_inner(
     .await?;
 
   // We execute the main module as a side module so that import.meta.main is not set.
-  worker.execute_side_module_possibly_with_npm().await?;
+  worker.execute_side_module().await?;
 
   let mut worker = worker.into_main_worker();
 
diff --git a/cli/tools/check.rs b/cli/tools/check.rs
index 7edb392d48..d880278884 100644
--- a/cli/tools/check.rs
+++ b/cli/tools/check.rs
@@ -32,6 +32,7 @@ use crate::graph_util::ModuleGraphBuilder;
 use crate::npm::CliNpmResolver;
 use crate::tsc;
 use crate::tsc::Diagnostics;
+use crate::tsc::TypeCheckingCjsTracker;
 use crate::util::extract;
 use crate::util::path::to_percent_decoded_str;
 
@@ -99,6 +100,7 @@ pub struct CheckOptions {
 
 pub struct TypeChecker {
   caches: Arc<Caches>,
+  cjs_tracker: Arc<TypeCheckingCjsTracker>,
   cli_options: Arc<CliOptions>,
   module_graph_builder: Arc<ModuleGraphBuilder>,
   node_resolver: Arc<NodeResolver>,
@@ -108,6 +110,7 @@ pub struct TypeChecker {
 impl TypeChecker {
   pub fn new(
     caches: Arc<Caches>,
+    cjs_tracker: Arc<TypeCheckingCjsTracker>,
     cli_options: Arc<CliOptions>,
     module_graph_builder: Arc<ModuleGraphBuilder>,
     node_resolver: Arc<NodeResolver>,
@@ -115,6 +118,7 @@ impl TypeChecker {
   ) -> Self {
     Self {
       caches,
+      cjs_tracker,
       cli_options,
       module_graph_builder,
       node_resolver,
@@ -244,6 +248,7 @@ impl TypeChecker {
       graph: graph.clone(),
       hash_data,
       maybe_npm: Some(tsc::RequestNpmState {
+        cjs_tracker: self.cjs_tracker.clone(),
         node_resolver: self.node_resolver.clone(),
         npm_resolver: self.npm_resolver.clone(),
       }),
@@ -346,7 +351,7 @@ fn get_check_hash(
             }
           }
           MediaType::Json
-          | MediaType::TsBuildInfo
+          | MediaType::Css
           | MediaType::SourceMap
           | MediaType::Wasm
           | MediaType::Unknown => continue,
@@ -428,7 +433,7 @@ fn get_tsc_roots(
         }
         MediaType::Json
         | MediaType::Wasm
-        | MediaType::TsBuildInfo
+        | MediaType::Css
         | MediaType::SourceMap
         | MediaType::Unknown => None,
       },
@@ -536,7 +541,7 @@ fn has_ts_check(media_type: MediaType, file_text: &str) -> bool {
     | MediaType::Tsx
     | MediaType::Json
     | MediaType::Wasm
-    | MediaType::TsBuildInfo
+    | MediaType::Css
     | MediaType::SourceMap
     | MediaType::Unknown => false,
   }
diff --git a/cli/tools/compile.rs b/cli/tools/compile.rs
index c1f98bc08a..b3e9993379 100644
--- a/cli/tools/compile.rs
+++ b/cli/tools/compile.rs
@@ -5,6 +5,7 @@ use crate::args::CompileFlags;
 use crate::args::Flags;
 use crate::factory::CliFactory;
 use crate::http_util::HttpClientProvider;
+use crate::standalone::binary::StandaloneRelativeFileBaseUrl;
 use crate::standalone::is_standalone_binary;
 use deno_ast::ModuleSpecifier;
 use deno_core::anyhow::bail;
@@ -14,7 +15,6 @@ use deno_core::error::AnyError;
 use deno_core::resolve_url_or_path;
 use deno_graph::GraphKind;
 use deno_terminal::colors;
-use eszip::EszipRelativeFileBaseUrl;
 use rand::Rng;
 use std::path::Path;
 use std::path::PathBuf;
@@ -29,7 +29,6 @@ pub async fn compile(
   let factory = CliFactory::from_flags(flags);
   let cli_options = factory.cli_options()?;
   let module_graph_creator = factory.module_graph_creator().await?;
-  let parsed_source_cache = factory.parsed_source_cache();
   let binary_writer = factory.create_compile_binary_writer().await?;
   let http_client = factory.http_client_provider();
   let module_specifier = cli_options.resolve_main_module()?;
@@ -70,7 +69,7 @@ pub async fn compile(
   let graph = if cli_options.type_check_mode().is_true() {
     // In this case, the previous graph creation did type checking, which will
     // create a module graph with types information in it. We don't want to
-    // store that in the eszip so create a code only module graph from scratch.
+    // store that in the binary so create a code only module graph from scratch.
     module_graph_creator
       .create_graph(GraphKind::CodeOnly, module_roots)
       .await?
@@ -81,11 +80,6 @@ pub async fn compile(
   let ts_config_for_emit = cli_options
     .resolve_ts_config_for_emit(deno_config::deno_json::TsConfigType::Emit)?;
   check_warn_tsconfig(&ts_config_for_emit);
-  let (transpile_options, emit_options) =
-    crate::args::ts_config_to_transpile_and_emit_options(
-      ts_config_for_emit.ts_config,
-    )?;
-  let parser = parsed_source_cache.as_capturing_parser();
   let root_dir_url = resolve_root_dir_from_specifiers(
     cli_options.workspace().root_dir(),
     graph.specifiers().map(|(s, _)| s).chain(
@@ -96,17 +90,6 @@ pub async fn compile(
     ),
   );
   log::debug!("Binary root dir: {}", root_dir_url);
-  let root_dir_url = EszipRelativeFileBaseUrl::new(&root_dir_url);
-  let eszip = eszip::EszipV2::from_graph(eszip::FromGraphOptions {
-    graph,
-    parser,
-    transpile_options,
-    emit_options,
-    // make all the modules relative to the root folder
-    relative_file_base: Some(root_dir_url),
-    npm_packages: None,
-  })?;
-
   log::info!(
     "{} {} to {}",
     colors::green("Compile"),
@@ -133,15 +116,18 @@ pub async fn compile(
   let write_result = binary_writer
     .write_bin(
       file,
-      eszip,
-      root_dir_url,
+      &graph,
+      StandaloneRelativeFileBaseUrl::from(&root_dir_url),
       module_specifier,
       &compile_flags,
       cli_options,
     )
     .await
     .with_context(|| {
-      format!("Writing temporary file '{}'", temp_path.display())
+      format!(
+        "Writing deno compile executable to temporary file '{}'",
+        temp_path.display()
+      )
     });
 
   // set it as executable
diff --git a/cli/tools/coverage/mod.rs b/cli/tools/coverage/mod.rs
index 260c0c8424..f593332475 100644
--- a/cli/tools/coverage/mod.rs
+++ b/cli/tools/coverage/mod.rs
@@ -6,12 +6,12 @@ use crate::args::FileFlags;
 use crate::args::Flags;
 use crate::cdp;
 use crate::factory::CliFactory;
-use crate::npm::CliNpmResolver;
 use crate::tools::fmt::format_json;
 use crate::tools::test::is_supported_test_path;
 use crate::util::text_encoding::source_map_from_code;
 
 use deno_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_ast::ModuleSpecifier;
 use deno_config::glob::FileCollector;
 use deno_config::glob::FilePatterns;
@@ -25,6 +25,7 @@ use deno_core::serde_json;
 use deno_core::sourcemap::SourceMap;
 use deno_core::url::Url;
 use deno_core::LocalInspectorSession;
+use node_resolver::InNpmPackageChecker;
 use regex::Regex;
 use std::fs;
 use std::fs::File;
@@ -327,6 +328,7 @@ fn generate_coverage_report(
 
   coverage_report.found_lines =
     if let Some(source_map) = maybe_source_map.as_ref() {
+      let script_source_lines = script_source.lines().collect::<Vec<_>>();
       let mut found_lines = line_counts
         .iter()
         .enumerate()
@@ -334,7 +336,23 @@ fn generate_coverage_report(
           // get all the mappings from this destination line to a different src line
           let mut results = source_map
             .tokens()
-            .filter(move |token| token.get_dst_line() as usize == index)
+            .filter(|token| {
+              let dst_line = token.get_dst_line() as usize;
+              dst_line == index && {
+                let dst_col = token.get_dst_col() as usize;
+                let content = script_source_lines
+                  .get(dst_line)
+                  .and_then(|line| {
+                    line.get(dst_col..std::cmp::min(dst_col + 2, line.len()))
+                  })
+                  .unwrap_or("");
+
+                !content.is_empty()
+                  && content != "/*"
+                  && content != "*/"
+                  && content != "//"
+              }
+            })
             .map(move |token| (token.get_src_line() as usize, *count))
             .collect::<Vec<_>>();
           // only keep the results that point at different src lines
@@ -444,7 +462,7 @@ fn filter_coverages(
   coverages: Vec<cdp::ScriptCoverage>,
   include: Vec<String>,
   exclude: Vec<String>,
-  npm_resolver: &dyn CliNpmResolver,
+  in_npm_pkg_checker: &dyn InNpmPackageChecker,
 ) -> Vec<cdp::ScriptCoverage> {
   let include: Vec<Regex> =
     include.iter().map(|e| Regex::new(e).unwrap()).collect();
@@ -468,7 +486,7 @@ fn filter_coverages(
         || doc_test_re.is_match(e.url.as_str())
         || Url::parse(&e.url)
           .ok()
-          .map(|url| npm_resolver.in_npm_package(&url))
+          .map(|url| in_npm_pkg_checker.in_npm_package(&url))
           .unwrap_or(false);
 
       let is_included = include.iter().any(|p| p.is_match(&e.url));
@@ -479,7 +497,7 @@ fn filter_coverages(
     .collect::<Vec<cdp::ScriptCoverage>>()
 }
 
-pub async fn cover_files(
+pub fn cover_files(
   flags: Arc<Flags>,
   coverage_flags: CoverageFlags,
 ) -> Result<(), AnyError> {
@@ -489,9 +507,10 @@ pub async fn cover_files(
 
   let factory = CliFactory::from_flags(flags);
   let cli_options = factory.cli_options()?;
-  let npm_resolver = factory.npm_resolver().await?;
+  let in_npm_pkg_checker = factory.in_npm_pkg_checker()?;
   let file_fetcher = factory.file_fetcher()?;
   let emitter = factory.emitter()?;
+  let cjs_tracker = factory.cjs_tracker()?;
 
   assert!(!coverage_flags.files.include.is_empty());
 
@@ -511,7 +530,7 @@ pub async fn cover_files(
     script_coverages,
     coverage_flags.include,
     coverage_flags.exclude,
-    npm_resolver.as_ref(),
+    in_npm_pkg_checker.as_ref(),
   );
   if script_coverages.is_empty() {
     return Err(generic_error("No covered files included in the report"));
@@ -568,16 +587,21 @@ pub async fn cover_files(
     let transpiled_code = match file.media_type {
       MediaType::JavaScript
       | MediaType::Unknown
+      | MediaType::Css
+      | MediaType::Wasm
       | MediaType::Cjs
       | MediaType::Mjs
       | MediaType::Json => None,
-      MediaType::Dts | MediaType::Dmts | MediaType::Dcts => Some(Vec::new()),
+      MediaType::Dts | MediaType::Dmts | MediaType::Dcts => Some(String::new()),
       MediaType::TypeScript
       | MediaType::Jsx
       | MediaType::Mts
       | MediaType::Cts
       | MediaType::Tsx => {
-        Some(match emitter.maybe_cached_emit(&file.specifier, &file.source) {
+        let module_kind = ModuleKind::from_is_cjs(
+          cjs_tracker.is_maybe_cjs(&file.specifier, file.media_type)?,
+        );
+        Some(match emitter.maybe_cached_emit(&file.specifier, module_kind, &file.source) {
           Some(code) => code,
           None => {
             return Err(anyhow!(
@@ -588,13 +612,12 @@ pub async fn cover_files(
           }
         })
       }
-      MediaType::Wasm | MediaType::TsBuildInfo | MediaType::SourceMap => {
+      MediaType::SourceMap => {
         unreachable!()
       }
     };
     let runtime_code: String = match transpiled_code {
-      Some(code) => String::from_utf8(code)
-        .with_context(|| format!("Failed decoding {}", file.specifier))?,
+      Some(code) => code,
       None => original_source.to_string(),
     };
 
diff --git a/cli/tools/doc.rs b/cli/tools/doc.rs
index 5e18546a28..e33da4efb2 100644
--- a/cli/tools/doc.rs
+++ b/cli/tools/doc.rs
@@ -22,9 +22,9 @@ use deno_core::serde_json;
 use deno_doc as doc;
 use deno_doc::html::UrlResolveKind;
 use deno_graph::source::NullFileSystem;
+use deno_graph::EsParser;
 use deno_graph::GraphKind;
 use deno_graph::ModuleAnalyzer;
-use deno_graph::ModuleParser;
 use deno_graph::ModuleSpecifier;
 use doc::html::ShortPath;
 use doc::DocDiagnostic;
@@ -37,7 +37,7 @@ const JSON_SCHEMA_VERSION: u8 = 1;
 
 async fn generate_doc_nodes_for_builtin_types(
   doc_flags: DocFlags,
-  parser: &dyn ModuleParser,
+  parser: &dyn EsParser,
   analyzer: &dyn ModuleAnalyzer,
 ) -> Result<IndexMap<ModuleSpecifier, Vec<doc::DocNode>>, AnyError> {
   let source_file_specifier =
@@ -96,7 +96,7 @@ pub async fn doc(
   let module_info_cache = factory.module_info_cache()?;
   let parsed_source_cache = factory.parsed_source_cache();
   let capturing_parser = parsed_source_cache.as_capturing_parser();
-  let analyzer = module_info_cache.as_module_analyzer(parsed_source_cache);
+  let analyzer = module_info_cache.as_module_analyzer();
 
   let doc_nodes_by_url = match doc_flags.source_files {
     DocSourceFileFlag::Builtin => {
diff --git a/cli/tools/fmt.rs b/cli/tools/fmt.rs
index 8a4bc4e6c8..81af25c34b 100644
--- a/cli/tools/fmt.rs
+++ b/cli/tools/fmt.rs
@@ -978,6 +978,7 @@ fn get_resolved_malva_config(
     single_line_top_level_declarations: false,
     selector_override_comment_directive: "deno-fmt-selector-override".into(),
     ignore_comment_directive: "deno-fmt-ignore".into(),
+    ignore_file_comment_directive: "deno-fmt-ignore-file".into(),
   };
 
   FormatOptions {
@@ -1036,6 +1037,7 @@ fn get_resolved_markup_fmt_config(
     svelte_directive_shorthand: Some(true),
     astro_attr_shorthand: Some(true),
     ignore_comment_directive: "deno-fmt-ignore".into(),
+    ignore_file_comment_directive: "deno-fmt-ignore-file".into(),
   };
 
   FormatOptions {
diff --git a/cli/tools/info.rs b/cli/tools/info.rs
index 1c83abe3bb..b53485bd6b 100644
--- a/cli/tools/info.rs
+++ b/cli/tools/info.rs
@@ -11,12 +11,14 @@ use deno_core::anyhow::bail;
 use deno_core::error::AnyError;
 use deno_core::resolve_url_or_path;
 use deno_core::serde_json;
+use deno_core::url;
 use deno_graph::Dependency;
 use deno_graph::GraphKind;
 use deno_graph::Module;
 use deno_graph::ModuleError;
 use deno_graph::ModuleGraph;
 use deno_graph::Resolution;
+use deno_npm::npm_rc::ResolvedNpmRc;
 use deno_npm::resolution::NpmResolutionSnapshot;
 use deno_npm::NpmPackageId;
 use deno_npm::NpmResolutionPackage;
@@ -47,20 +49,23 @@ pub async fn info(
     let module_graph_creator = factory.module_graph_creator().await?;
     let npm_resolver = factory.npm_resolver().await?;
     let maybe_lockfile = cli_options.maybe_lockfile();
+    let npmrc = cli_options.npmrc();
     let resolver = factory.workspace_resolver().await?;
 
-    let maybe_import_specifier =
-      if let Some(import_map) = resolver.maybe_import_map() {
-        if let Ok(imports_specifier) =
-          import_map.resolve(&specifier, import_map.base_url())
-        {
-          Some(imports_specifier)
-        } else {
-          None
-        }
+    let cwd_url =
+      url::Url::from_directory_path(cli_options.initial_cwd()).unwrap();
+
+    let maybe_import_specifier = if let Some(import_map) =
+      resolver.maybe_import_map()
+    {
+      if let Ok(imports_specifier) = import_map.resolve(&specifier, &cwd_url) {
+        Some(imports_specifier)
       } else {
         None
-      };
+      }
+    } else {
+      None
+    };
 
     let specifier = match maybe_import_specifier {
       Some(specifier) => specifier,
@@ -88,7 +93,8 @@ pub async fn info(
           JSON_SCHEMA_VERSION.into(),
         );
       }
-      add_npm_packages_to_json(&mut json_graph, npm_resolver.as_ref());
+
+      add_npm_packages_to_json(&mut json_graph, npm_resolver.as_ref(), npmrc);
       display::write_json_to_stdout(&json_graph)?;
     } else {
       let mut output = String::new();
@@ -185,6 +191,7 @@ fn print_cache_info(
 fn add_npm_packages_to_json(
   json: &mut serde_json::Value,
   npm_resolver: &dyn CliNpmResolver,
+  npmrc: &ResolvedNpmRc,
 ) {
   let Some(npm_resolver) = npm_resolver.as_managed() else {
     return; // does not include byonm to deno info's output
@@ -195,45 +202,28 @@ fn add_npm_packages_to_json(
   let json = json.as_object_mut().unwrap();
   let modules = json.get_mut("modules").and_then(|m| m.as_array_mut());
   if let Some(modules) = modules {
-    if modules.len() == 1
-      && modules[0].get("kind").and_then(|k| k.as_str()) == Some("npm")
-    {
-      // If there is only one module and it's "external", then that means
-      // someone provided an npm specifier as a cli argument. In this case,
-      // we want to show which npm package the cli argument resolved to.
-      let module = &mut modules[0];
-      let maybe_package = module
-        .get("specifier")
-        .and_then(|k| k.as_str())
-        .and_then(|specifier| NpmPackageNvReference::from_str(specifier).ok())
-        .and_then(|package_ref| {
-          snapshot
-            .resolve_package_from_deno_module(package_ref.nv())
-            .ok()
-        });
-      if let Some(pkg) = maybe_package {
-        if let Some(module) = module.as_object_mut() {
-          module
-            .insert("npmPackage".to_string(), pkg.id.as_serialized().into());
-        }
-      }
-    } else {
-      // Filter out npm package references from the modules and instead
-      // have them only listed as dependencies. This is done because various
-      // npm specifiers modules in the graph are really just unresolved
-      // references. So there could be listed multiple npm specifiers
-      // that would resolve to a single npm package.
-      for i in (0..modules.len()).rev() {
-        if matches!(
-          modules[i].get("kind").and_then(|k| k.as_str()),
-          Some("npm") | Some("external")
-        ) {
-          modules.remove(i);
-        }
-      }
-    }
-
     for module in modules.iter_mut() {
+      if matches!(module.get("kind").and_then(|k| k.as_str()), Some("npm")) {
+        // If there is only one module and it's "external", then that means
+        // someone provided an npm specifier as a cli argument. In this case,
+        // we want to show which npm package the cli argument resolved to.
+        let maybe_package = module
+          .get("specifier")
+          .and_then(|k| k.as_str())
+          .and_then(|specifier| NpmPackageNvReference::from_str(specifier).ok())
+          .and_then(|package_ref| {
+            snapshot
+              .resolve_package_from_deno_module(package_ref.nv())
+              .ok()
+          });
+        if let Some(pkg) = maybe_package {
+          if let Some(module) = module.as_object_mut() {
+            module
+              .insert("npmPackage".to_string(), pkg.id.as_serialized().into());
+          }
+        }
+      }
+
       let dependencies = module
         .get_mut("dependencies")
         .and_then(|d| d.as_array_mut());
@@ -265,7 +255,7 @@ fn add_npm_packages_to_json(
   let mut json_packages = serde_json::Map::with_capacity(sorted_packages.len());
   for pkg in sorted_packages {
     let mut kv = serde_json::Map::new();
-    kv.insert("name".to_string(), pkg.id.nv.name.to_string().into());
+    kv.insert("name".to_string(), pkg.id.nv.name.clone().into());
     kv.insert("version".to_string(), pkg.id.nv.version.to_string().into());
     let mut deps = pkg.dependencies.values().collect::<Vec<_>>();
     deps.sort();
@@ -274,6 +264,8 @@ fn add_npm_packages_to_json(
       .map(|id| serde_json::Value::String(id.as_serialized()))
       .collect::<Vec<_>>();
     kv.insert("dependencies".to_string(), deps.into());
+    let registry_url = npmrc.get_registry_url(&pkg.id.nv.name);
+    kv.insert("registryUrl".to_string(), registry_url.to_string().into());
 
     json_packages.insert(pkg.id.as_serialized(), kv.into());
   }
@@ -538,7 +530,7 @@ impl<'a> GraphDisplayContext<'a> {
 
   fn build_module_info(&mut self, module: &Module, type_dep: bool) -> TreeNode {
     enum PackageOrSpecifier {
-      Package(NpmResolutionPackage),
+      Package(Box<NpmResolutionPackage>),
       Specifier(ModuleSpecifier),
     }
 
@@ -546,7 +538,7 @@ impl<'a> GraphDisplayContext<'a> {
 
     let package_or_specifier = match module.npm() {
       Some(npm) => match self.npm_info.resolve_package(npm.nv_reference.nv()) {
-        Some(package) => Package(package.clone()),
+        Some(package) => Package(Box::new(package.clone())),
         None => Specifier(module.specifier().clone()), // should never happen
       },
       None => Specifier(module.specifier().clone()),
diff --git a/cli/tools/init/mod.rs b/cli/tools/init/mod.rs
index 2d6a894e13..4e4a686c5f 100644
--- a/cli/tools/init/mod.rs
+++ b/cli/tools/init/mod.rs
@@ -24,32 +24,29 @@ pub fn init_project(init_flags: InitFlags) -> Result<(), AnyError> {
     create_file(
       &dir,
       "main.ts",
-      r#"import { type Route, route, serveDir } from "@std/http";
+      r#"import { serveDir } from "@std/http";
 
-const routes: Route[] = [
-  {
-    pattern: new URLPattern({ pathname: "/" }),
-    handler: () => new Response("Home page"),
-  },
-  {
-    pattern: new URLPattern({ pathname: "/users/:id" }),
-    handler: (_req, _info, params) => new Response(params?.pathname.groups.id),
-  },
-  {
-    pattern: new URLPattern({ pathname: "/static/*" }),
-    handler: (req) => serveDir(req),
-  },
-];
-
-function defaultHandler(_req: Request) {
-  return new Response("Not found", { status: 404 });
-}
-
-const handler = route(routes, defaultHandler);
+const userPagePattern = new URLPattern({ pathname: "/users/:id" });
+const staticPathPattern = new URLPattern({ pathname: "/static/*" });
 
 export default {
   fetch(req) {
-    return handler(req);
+    const url = new URL(req.url);
+
+    if (url.pathname === "/") {
+      return new Response("Home page");
+    }
+
+    const userPageMatch = userPagePattern.exec(url);
+    if (userPageMatch) {
+      return new Response(userPageMatch.pathname.groups.id);
+    }
+
+    if (staticPathPattern.test(url)) {
+      return serveDir(req);
+    }
+
+    return new Response("Not found", { status: 404 });
   },
 } satisfies Deno.ServeDefaultExport;
 "#,
diff --git a/cli/tools/jupyter/install.rs b/cli/tools/jupyter/install.rs
index b0ddc948d6..aeff89ccf4 100644
--- a/cli/tools/jupyter/install.rs
+++ b/cli/tools/jupyter/install.rs
@@ -58,9 +58,9 @@ pub fn install() -> Result<(), AnyError> {
 
   let f = std::fs::File::create(kernel_json_path)?;
   serde_json::to_writer_pretty(f, &json_data)?;
-  install_icon(&user_data_dir, "logo-32x32.png", DENO_ICON_32)?;
-  install_icon(&user_data_dir, "logo-64x64.png", DENO_ICON_64)?;
-  install_icon(&user_data_dir, "logo-svg.svg", DENO_ICON_SVG)?;
+  install_icon(&kernel_dir, "logo-32x32.png", DENO_ICON_32)?;
+  install_icon(&kernel_dir, "logo-64x64.png", DENO_ICON_64)?;
+  install_icon(&kernel_dir, "logo-svg.svg", DENO_ICON_SVG)?;
 
   log::info!("✅ Deno kernelspec installed successfully.");
   Ok(())
diff --git a/cli/tools/jupyter/resources/deno-logo-32x32.png b/cli/tools/jupyter/resources/deno-logo-32x32.png
index 97871a02ee..d59f251a24 100644
Binary files a/cli/tools/jupyter/resources/deno-logo-32x32.png and b/cli/tools/jupyter/resources/deno-logo-32x32.png differ
diff --git a/cli/tools/jupyter/resources/deno-logo-64x64.png b/cli/tools/jupyter/resources/deno-logo-64x64.png
index 1b9444ef63..37e98abafd 100644
Binary files a/cli/tools/jupyter/resources/deno-logo-64x64.png and b/cli/tools/jupyter/resources/deno-logo-64x64.png differ
diff --git a/cli/tools/jupyter/resources/deno-logo-svg.svg b/cli/tools/jupyter/resources/deno-logo-svg.svg
index d7bb9ef804..fbc22cd910 100644
--- a/cli/tools/jupyter/resources/deno-logo-svg.svg
+++ b/cli/tools/jupyter/resources/deno-logo-svg.svg
@@ -1 +1,17 @@
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+<svg width="100%" height="100%" viewBox="0 0 441 441" version="1.1" xmlns="http://www.w3.org/2000/svg"
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+  style="fill-rule:evenodd;clip-rule:evenodd;stroke-linejoin:round;stroke-miterlimit:2;">
+  <g transform="matrix(1.02631,-2.08167e-17,2.08167e-17,1.02631,-0.525826,-0.525138)">
+    <path
+      d="M37.965,296.635C26.441,271.766 20.009,244.065 20.009,214.873C20.009,207.318 20.439,199.863 21.278,192.531C22.129,185.123 23.39,177.852 25.036,170.742C34.286,130.852 55.801,95.64 85.384,69.301C110.233,47.207 140.674,31.444 174.043,24.299C187.212,21.486 200.872,20.006 214.875,20.006C219.783,20.011 224.727,20.2 229.701,20.579C253.285,22.38 275.571,28.317 295.904,37.625C312.305,45.143 327.486,54.87 341.064,66.426C375.17,95.48 398.957,135.953 406.867,181.369C408.757,192.255 409.742,203.45 409.742,214.873C409.738,219.789 409.548,224.74 409.168,229.721C407.731,248.545 403.659,266.542 397.34,283.379C388.521,306.83 375.308,328.136 358.706,346.294C337.113,368.342 309.673,378.152 286.755,377.744C270.09,377.447 253.784,370.816 242.516,361.114C226.42,347.253 219.918,331.409 217.69,313.729C217.136,309.334 217.461,297.358 219.748,289.066C221.453,282.885 225.777,270.948 232.1,265.727C224.703,262.541 215.183,255.604 212.182,252.274C211.445,251.455 211.54,250.174 212.2,249.292C212.861,248.41 214.02,248.062 215.057,248.435C221.416,250.618 229.161,252.771 237.327,254.137C248.067,255.932 261.424,258.194 274.955,258.859C307.946,260.479 342.407,245.67 353.103,216.207C363.798,186.744 359.649,157.602 321.279,140.121C282.909,122.64 265.185,101.856 234.183,89.32C213.934,81.131 191.396,85.992 168.257,98.78C105.931,133.223 50.092,242.048 75.833,342.873C76.201,344.252 75.58,345.705 74.328,346.392C73.156,347.036 71.713,346.852 70.741,345.962C63.25,337.731 56.454,328.857 50.445,319.433C45.796,312.139 41.623,304.524 37.965,296.635Z" />
+  </g>
+  <g transform="matrix(0.0920293,0.00428099,-0.00428099,0.0920293,-28.1272,-500.301)">
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+      style="fill:white;" />
+  </g>
+  <g transform="matrix(7.12289,0.543899,-0.543899,7.12289,-4867.49,-1040.55)">
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+</svg>
diff --git a/cli/tools/jupyter/server.rs b/cli/tools/jupyter/server.rs
index 0cd80f7ddd..5680ed4c13 100644
--- a/cli/tools/jupyter/server.rs
+++ b/cli/tools/jupyter/server.rs
@@ -329,7 +329,12 @@ impl JupyterServer {
             })
             .collect();
 
-            (candidates, cursor_pos - prop_name.len())
+            if prop_name.len() > cursor_pos {
+              // TODO(bartlomieju): most likely not correct, but better than panicking because of sub with overflow
+              (candidates, cursor_pos)
+            } else {
+              (candidates, cursor_pos - prop_name.len())
+            }
           } else {
             // combine results of declarations and globalThis properties
             let mut candidates = get_expression_property_names(
@@ -349,7 +354,12 @@ impl JupyterServer {
             candidates.sort();
             candidates.dedup(); // make sure to sort first
 
-            (candidates, cursor_pos - expr.len())
+            if expr.len() > cursor_pos {
+              // TODO(bartlomieju): most likely not correct, but better than panicking because of sub with overflow
+              (candidates, cursor_pos)
+            } else {
+              (candidates, cursor_pos - expr.len())
+            }
           };
 
           connection
diff --git a/cli/tools/registry/pm.rs b/cli/tools/registry/pm.rs
index f56774e8eb..4e03879983 100644
--- a/cli/tools/registry/pm.rs
+++ b/cli/tools/registry/pm.rs
@@ -1,32 +1,23 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-mod cache_deps;
-
-pub use cache_deps::cache_top_level_deps;
-use deno_semver::jsr::JsrPackageReqReference;
-use deno_semver::npm::NpmPackageReqReference;
-use deno_semver::VersionReq;
-
-use std::borrow::Cow;
+use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
 
-use deno_ast::TextChange;
-use deno_config::deno_json::FmtOptionsConfig;
-use deno_core::anyhow::anyhow;
 use deno_core::anyhow::bail;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_core::futures::FutureExt;
 use deno_core::futures::StreamExt;
-use deno_core::serde_json;
-use deno_core::ModuleSpecifier;
-use deno_runtime::deno_node;
+use deno_path_util::url_to_file_path;
+use deno_semver::jsr::JsrPackageReqReference;
+use deno_semver::npm::NpmPackageReqReference;
 use deno_semver::package::PackageReq;
-use indexmap::IndexMap;
-use jsonc_parser::ast::ObjectProp;
-use jsonc_parser::ast::Value;
-use yoke::Yoke;
+use deno_semver::VersionReq;
+use jsonc_parser::cst::CstObject;
+use jsonc_parser::cst::CstObjectProp;
+use jsonc_parser::cst::CstRootNode;
+use jsonc_parser::json;
 
 use crate::args::AddFlags;
 use crate::args::CacheSetting;
@@ -38,234 +29,181 @@ use crate::file_fetcher::FileFetcher;
 use crate::jsr::JsrFetchResolver;
 use crate::npm::NpmFetchResolver;
 
-enum DenoConfigFormat {
-  Json,
-  Jsonc,
+mod cache_deps;
+
+pub use cache_deps::cache_top_level_deps;
+
+#[derive(Debug, Copy, Clone)]
+enum ConfigKind {
+  DenoJson,
+  PackageJson,
 }
 
-impl DenoConfigFormat {
-  fn from_specifier(spec: &ModuleSpecifier) -> Result<Self, AnyError> {
-    let file_name = spec
-      .path_segments()
-      .ok_or_else(|| anyhow!("Empty path in deno config specifier: {spec}"))?
-      .last()
-      .unwrap();
-    match file_name {
-      "deno.json" => Ok(Self::Json),
-      "deno.jsonc" => Ok(Self::Jsonc),
-      _ => bail!("Unsupported deno config file: {file_name}"),
-    }
-  }
-}
-
-struct DenoConfig {
-  config: Arc<deno_config::deno_json::ConfigFile>,
-  format: DenoConfigFormat,
-  imports: IndexMap<String, String>,
-}
-
-fn deno_json_imports(
-  config: &deno_config::deno_json::ConfigFile,
-) -> Result<IndexMap<String, String>, AnyError> {
-  Ok(
-    config
-      .json
-      .imports
-      .clone()
-      .map(|imports| {
-        serde_json::from_value(imports)
-          .map_err(|err| anyhow!("Malformed \"imports\" configuration: {err}"))
-      })
-      .transpose()?
-      .unwrap_or_default(),
-  )
-}
-impl DenoConfig {
-  fn from_options(options: &CliOptions) -> Result<Option<Self>, AnyError> {
-    let start_dir = &options.start_dir;
-    if let Some(config) = start_dir.maybe_deno_json() {
-      Ok(Some(Self {
-        imports: deno_json_imports(config)?,
-        config: config.clone(),
-        format: DenoConfigFormat::from_specifier(&config.specifier)?,
-      }))
-    } else {
-      Ok(None)
-    }
-  }
-
-  fn add(&mut self, selected: SelectedPackage) {
-    self.imports.insert(
-      selected.import_name,
-      format!("{}@{}", selected.package_name, selected.version_req),
-    );
-  }
-
-  fn remove(&mut self, package: &str) -> bool {
-    self.imports.shift_remove(package).is_some()
-  }
-
-  fn take_import_fields(
-    &mut self,
-  ) -> Vec<(&'static str, IndexMap<String, String>)> {
-    vec![("imports", std::mem::take(&mut self.imports))]
-  }
-}
-
-impl NpmConfig {
-  fn from_options(options: &CliOptions) -> Result<Option<Self>, AnyError> {
-    let start_dir = &options.start_dir;
-    if let Some(pkg_json) = start_dir.maybe_pkg_json() {
-      Ok(Some(Self {
-        dependencies: pkg_json.dependencies.clone().unwrap_or_default(),
-        dev_dependencies: pkg_json.dev_dependencies.clone().unwrap_or_default(),
-        config: pkg_json.clone(),
-        fmt_options: None,
-      }))
-    } else {
-      Ok(None)
-    }
-  }
-
-  fn add(&mut self, selected: SelectedPackage, dev: bool) {
-    let (name, version) = package_json_dependency_entry(selected);
-    if dev {
-      self.dev_dependencies.insert(name, version);
-    } else {
-      self.dependencies.insert(name, version);
-    }
-  }
-
-  fn remove(&mut self, package: &str) -> bool {
-    let in_deps = self.dependencies.shift_remove(package).is_some();
-    let in_dev_deps = self.dev_dependencies.shift_remove(package).is_some();
-    in_deps || in_dev_deps
-  }
-
-  fn take_import_fields(
-    &mut self,
-  ) -> Vec<(&'static str, IndexMap<String, String>)> {
-    vec![
-      ("dependencies", std::mem::take(&mut self.dependencies)),
-      (
-        "devDependencies",
-        std::mem::take(&mut self.dev_dependencies),
-      ),
-    ]
-  }
-}
-
-struct NpmConfig {
-  config: Arc<deno_node::PackageJson>,
-  fmt_options: Option<FmtOptionsConfig>,
-  dependencies: IndexMap<String, String>,
-  dev_dependencies: IndexMap<String, String>,
-}
-
-enum DenoOrPackageJson {
-  Deno(DenoConfig),
-  Npm(NpmConfig),
-}
-
-impl From<DenoConfig> for DenoOrPackageJson {
-  fn from(config: DenoConfig) -> Self {
-    Self::Deno(config)
-  }
-}
-
-impl From<NpmConfig> for DenoOrPackageJson {
-  fn from(config: NpmConfig) -> Self {
-    Self::Npm(config)
-  }
-}
-
-/// Wrapper around `jsonc_parser::ast::Object` that can be stored in a `Yoke`
-#[derive(yoke::Yokeable)]
-struct JsoncObjectView<'a>(jsonc_parser::ast::Object<'a>);
-
 struct ConfigUpdater {
-  config: DenoOrPackageJson,
-  // the `Yoke` is so we can carry the parsed object (which borrows from
-  // the source) along with the source itself
-  ast: Yoke<JsoncObjectView<'static>, String>,
+  kind: ConfigKind,
+  cst: CstRootNode,
+  root_object: CstObject,
   path: PathBuf,
   modified: bool,
 }
 
 impl ConfigUpdater {
-  fn obj(&self) -> &jsonc_parser::ast::Object<'_> {
-    &self.ast.get().0
-  }
-  fn contents(&self) -> &str {
-    self.ast.backing_cart()
-  }
-  async fn maybe_new(
-    config: Option<impl Into<DenoOrPackageJson>>,
-  ) -> Result<Option<Self>, AnyError> {
-    if let Some(config) = config {
-      Ok(Some(Self::new(config.into()).await?))
-    } else {
-      Ok(None)
-    }
-  }
-  async fn new(config: DenoOrPackageJson) -> Result<Self, AnyError> {
-    let specifier = config.specifier();
-    if specifier.scheme() != "file" {
-      bail!("Can't update a remote configuration file");
-    }
-    let config_file_path = specifier.to_file_path().map_err(|_| {
-      anyhow!("Specifier {specifier:?} is an invalid file path")
-    })?;
-    let config_file_contents = {
-      let contents = tokio::fs::read_to_string(&config_file_path)
-        .await
-        .with_context(|| {
-          format!("Reading config file at: {}", config_file_path.display())
-        })?;
-      if contents.trim().is_empty() {
-        "{}\n".into()
-      } else {
-        contents
-      }
-    };
-    let ast = Yoke::try_attach_to_cart(config_file_contents, |contents| {
-      let ast = jsonc_parser::parse_to_ast(
-        contents,
-        &Default::default(),
-        &Default::default(),
-      )
+  fn new(
+    kind: ConfigKind,
+    config_file_path: PathBuf,
+  ) -> Result<Self, AnyError> {
+    let config_file_contents = std::fs::read_to_string(&config_file_path)
       .with_context(|| {
-        format!("Failed to parse config file at {}", specifier)
+        format!("Reading config file '{}'", config_file_path.display())
       })?;
-      let obj = match ast.value {
-        Some(Value::Object(obj)) => obj,
-        _ => bail!(
-          "Failed to update config file at {}, expected an object",
-          specifier
-        ),
-      };
-      Ok(JsoncObjectView(obj))
-    })?;
+    let cst = CstRootNode::parse(&config_file_contents, &Default::default())
+      .with_context(|| {
+        format!("Parsing config file '{}'", config_file_path.display())
+      })?;
+    let root_object = cst.object_value_or_set();
     Ok(Self {
-      config,
-      ast,
+      kind,
+      cst,
+      root_object,
       path: config_file_path,
       modified: false,
     })
   }
 
+  fn display_path(&self) -> String {
+    deno_path_util::url_from_file_path(&self.path)
+      .map(|u| u.to_string())
+      .unwrap_or_else(|_| self.path.display().to_string())
+  }
+
+  fn obj(&self) -> &CstObject {
+    &self.root_object
+  }
+
+  fn contents(&self) -> String {
+    self.cst.to_string()
+  }
+
   fn add(&mut self, selected: SelectedPackage, dev: bool) {
-    match &mut self.config {
-      DenoOrPackageJson::Deno(deno) => deno.add(selected),
-      DenoOrPackageJson::Npm(npm) => npm.add(selected, dev),
+    fn insert_index(object: &CstObject, searching_name: &str) -> usize {
+      object
+        .properties()
+        .into_iter()
+        .take_while(|prop| {
+          let prop_name =
+            prop.name().and_then(|name| name.decoded_value().ok());
+          match prop_name {
+            Some(current_name) => {
+              searching_name.cmp(&current_name) == std::cmp::Ordering::Greater
+            }
+            None => true,
+          }
+        })
+        .count()
     }
+
+    match self.kind {
+      ConfigKind::DenoJson => {
+        let imports = self.root_object.object_value_or_set("imports");
+        let value =
+          format!("{}@{}", selected.package_name, selected.version_req);
+        if let Some(prop) = imports.get(&selected.import_name) {
+          prop.set_value(json!(value));
+        } else {
+          let index = insert_index(&imports, &selected.import_name);
+          imports.insert(index, &selected.import_name, json!(value));
+        }
+      }
+      ConfigKind::PackageJson => {
+        let deps_prop = self.root_object.get("dependencies");
+        let dev_deps_prop = self.root_object.get("devDependencies");
+
+        let dependencies = if dev {
+          self
+            .root_object
+            .object_value("devDependencies")
+            .unwrap_or_else(|| {
+              let index = deps_prop
+                .as_ref()
+                .map(|p| p.property_index() + 1)
+                .unwrap_or_else(|| self.root_object.properties().len());
+              self
+                .root_object
+                .insert(index, "devDependencies", json!({}))
+                .object_value_or_set()
+            })
+        } else {
+          self
+            .root_object
+            .object_value("dependencies")
+            .unwrap_or_else(|| {
+              let index = dev_deps_prop
+                .as_ref()
+                .map(|p| p.property_index())
+                .unwrap_or_else(|| self.root_object.properties().len());
+              self
+                .root_object
+                .insert(index, "dependencies", json!({}))
+                .object_value_or_set()
+            })
+        };
+        let other_dependencies = if dev {
+          deps_prop.and_then(|p| p.value().and_then(|v| v.as_object()))
+        } else {
+          dev_deps_prop.and_then(|p| p.value().and_then(|v| v.as_object()))
+        };
+
+        let (alias, value) = package_json_dependency_entry(selected);
+
+        if let Some(other) = other_dependencies {
+          if let Some(prop) = other.get(&alias) {
+            remove_prop_and_maybe_parent_prop(prop);
+          }
+        }
+
+        if let Some(prop) = dependencies.get(&alias) {
+          prop.set_value(json!(value));
+        } else {
+          let index = insert_index(&dependencies, &alias);
+          dependencies.insert(index, &alias, json!(value));
+        }
+      }
+    }
+
     self.modified = true;
   }
 
   fn remove(&mut self, package: &str) -> bool {
-    let removed = match &mut self.config {
-      DenoOrPackageJson::Deno(deno) => deno.remove(package),
-      DenoOrPackageJson::Npm(npm) => npm.remove(package),
+    let removed = match self.kind {
+      ConfigKind::DenoJson => {
+        if let Some(prop) = self
+          .root_object
+          .object_value("imports")
+          .and_then(|i| i.get(package))
+        {
+          remove_prop_and_maybe_parent_prop(prop);
+          true
+        } else {
+          false
+        }
+      }
+      ConfigKind::PackageJson => {
+        let deps = [
+          self
+            .root_object
+            .object_value("dependencies")
+            .and_then(|deps| deps.get(package)),
+          self
+            .root_object
+            .object_value("devDependencies")
+            .and_then(|deps| deps.get(package)),
+        ];
+        let removed = deps.iter().any(|d| d.is_some());
+        for dep in deps.into_iter().flatten() {
+          remove_prop_and_maybe_parent_prop(dep);
+        }
+        removed
+      }
     };
     if removed {
       self.modified = true;
@@ -273,76 +211,28 @@ impl ConfigUpdater {
     removed
   }
 
-  async fn commit(mut self) -> Result<(), AnyError> {
+  fn commit(&self) -> Result<(), AnyError> {
     if !self.modified {
       return Ok(());
     }
 
-    let import_fields = self.config.take_import_fields();
-
-    let fmt_config_options = self.config.fmt_options();
-
-    let new_text = update_config_file_content(
-      self.obj(),
-      self.contents(),
-      fmt_config_options,
-      import_fields.into_iter().map(|(k, v)| {
-        (
-          k,
-          if v.is_empty() {
-            None
-          } else {
-            Some(generate_imports(v.into_iter().collect()))
-          },
-        )
-      }),
-      self.config.file_name(),
-    );
-
-    tokio::fs::write(&self.path, new_text).await?;
+    let new_text = self.contents();
+    std::fs::write(&self.path, new_text).with_context(|| {
+      format!("failed writing to '{}'", self.path.display())
+    })?;
     Ok(())
   }
 }
 
-impl DenoOrPackageJson {
-  fn specifier(&self) -> Cow<ModuleSpecifier> {
-    match self {
-      Self::Deno(d, ..) => Cow::Borrowed(&d.config.specifier),
-      Self::Npm(n, ..) => Cow::Owned(n.config.specifier()),
-    }
-  }
-
-  fn fmt_options(&self) -> FmtOptionsConfig {
-    match self {
-      DenoOrPackageJson::Deno(deno, ..) => deno
-        .config
-        .to_fmt_config()
-        .ok()
-        .map(|f| f.options)
-        .unwrap_or_default(),
-      DenoOrPackageJson::Npm(config) => {
-        config.fmt_options.clone().unwrap_or_default()
-      }
-    }
-  }
-
-  fn take_import_fields(
-    &mut self,
-  ) -> Vec<(&'static str, IndexMap<String, String>)> {
-    match self {
-      Self::Deno(d) => d.take_import_fields(),
-      Self::Npm(n) => n.take_import_fields(),
-    }
-  }
-
-  fn file_name(&self) -> &'static str {
-    match self {
-      DenoOrPackageJson::Deno(config) => match config.format {
-        DenoConfigFormat::Json => "deno.json",
-        DenoConfigFormat::Jsonc => "deno.jsonc",
-      },
-      DenoOrPackageJson::Npm(..) => "package.json",
-    }
+fn remove_prop_and_maybe_parent_prop(prop: CstObjectProp) {
+  let parent = prop.parent().unwrap().as_object().unwrap();
+  prop.remove();
+  if parent.properties().is_empty() {
+    let parent_property = parent.parent().unwrap();
+    let root_object = parent_property.parent().unwrap().as_object().unwrap();
+    // remove the property
+    parent_property.remove();
+    root_object.ensure_multiline();
   }
 }
 
@@ -361,7 +251,14 @@ fn package_json_dependency_entry(
   selected: SelectedPackage,
 ) -> (String, String) {
   if let Some(npm_package) = selected.package_name.strip_prefix("npm:") {
-    (npm_package.into(), selected.version_req)
+    if selected.import_name == npm_package {
+      (npm_package.into(), selected.version_req)
+    } else {
+      (
+        selected.import_name,
+        format!("npm:{}@{}", npm_package, selected.version_req),
+      )
+    }
   } else if let Some(jsr_package) = selected.package_name.strip_prefix("jsr:") {
     let jsr_package = jsr_package.strip_prefix('@').unwrap_or(jsr_package);
     let scope_replaced = jsr_package.replace('/', "__");
@@ -391,21 +288,45 @@ impl std::fmt::Display for AddCommandName {
 
 fn load_configs(
   flags: &Arc<Flags>,
-) -> Result<(CliFactory, Option<NpmConfig>, Option<DenoConfig>), AnyError> {
+  has_jsr_specifiers: impl FnOnce() -> bool,
+) -> Result<(CliFactory, Option<ConfigUpdater>, Option<ConfigUpdater>), AnyError>
+{
   let cli_factory = CliFactory::from_flags(flags.clone());
   let options = cli_factory.cli_options()?;
-  let npm_config = NpmConfig::from_options(options)?;
-  let (cli_factory, deno_config) = match DenoConfig::from_options(options)? {
+  let start_dir = &options.start_dir;
+  let npm_config = match start_dir.maybe_pkg_json() {
+    Some(pkg_json) => Some(ConfigUpdater::new(
+      ConfigKind::PackageJson,
+      pkg_json.path.clone(),
+    )?),
+    None => None,
+  };
+  let deno_config = match start_dir.maybe_deno_json() {
+    Some(deno_json) => Some(ConfigUpdater::new(
+      ConfigKind::DenoJson,
+      url_to_file_path(&deno_json.specifier)?,
+    )?),
+    None => None,
+  };
+
+  let (cli_factory, deno_config) = match deno_config {
     Some(config) => (cli_factory, Some(config)),
-    None if npm_config.is_some() => (cli_factory, None),
-    None => {
+    None if npm_config.is_some() && !has_jsr_specifiers() => {
+      (cli_factory, None)
+    }
+    _ => {
       let factory = create_deno_json(flags, options)?;
       let options = factory.cli_options()?.clone();
+      let deno_json = options
+        .start_dir
+        .maybe_deno_json()
+        .expect("Just created deno.json");
       (
         factory,
-        Some(
-          DenoConfig::from_options(&options)?.expect("Just created deno.json"),
-        ),
+        Some(ConfigUpdater::new(
+          ConfigKind::DenoJson,
+          url_to_file_path(&deno_json.specifier)?,
+        )?),
       )
     }
   };
@@ -413,18 +334,26 @@ fn load_configs(
   Ok((cli_factory, npm_config, deno_config))
 }
 
+fn path_distance(a: &Path, b: &Path) -> usize {
+  let diff = pathdiff::diff_paths(a, b);
+  let Some(diff) = diff else {
+    return usize::MAX;
+  };
+  diff.components().count()
+}
+
 pub async fn add(
   flags: Arc<Flags>,
   add_flags: AddFlags,
   cmd_name: AddCommandName,
 ) -> Result<(), AnyError> {
-  let (cli_factory, npm_config, deno_config) = load_configs(&flags)?;
-  let mut npm_config = ConfigUpdater::maybe_new(npm_config).await?;
-  let mut deno_config = ConfigUpdater::maybe_new(deno_config).await?;
+  let (cli_factory, mut npm_config, mut deno_config) =
+    load_configs(&flags, || {
+      add_flags.packages.iter().any(|s| s.starts_with("jsr:"))
+    })?;
 
   if let Some(deno) = &deno_config {
-    let specifier = deno.config.specifier();
-    if deno.obj().get_string("importMap").is_some() {
+    if deno.obj().get("importMap").is_some() {
       bail!(
         concat!(
           "`deno {}` is not supported when configuration file contains an \"importMap\" field. ",
@@ -432,11 +361,26 @@ pub async fn add(
           "    at {}",
         ),
         cmd_name,
-        specifier
+        deno.display_path(),
       );
     }
   }
 
+  let start_dir = cli_factory.cli_options()?.start_dir.dir_path();
+
+  // only prefer to add npm deps to `package.json` if there isn't a closer deno.json.
+  // example: if deno.json is in the CWD and package.json is in the parent, we should add
+  // npm deps to deno.json, since it's closer
+  let prefer_npm_config = match (npm_config.as_ref(), deno_config.as_ref()) {
+    (Some(npm), Some(deno)) => {
+      let npm_distance = path_distance(&npm.path, &start_dir);
+      let deno_distance = path_distance(&deno.path, &start_dir);
+      npm_distance <= deno_distance
+    }
+    (Some(_), None) => true,
+    (None, _) => false,
+  };
+
   let http_client = cli_factory.http_client_provider();
   let deps_http_cache = cli_factory.global_http_cache()?;
   let mut deps_file_fetcher = FileFetcher::new(
@@ -447,16 +391,20 @@ pub async fn add(
     Default::default(),
     None,
   );
+
+  let npmrc = cli_factory.cli_options().unwrap().npmrc();
+
   deps_file_fetcher.set_download_log_level(log::Level::Trace);
   let deps_file_fetcher = Arc::new(deps_file_fetcher);
   let jsr_resolver = Arc::new(JsrFetchResolver::new(deps_file_fetcher.clone()));
-  let npm_resolver = Arc::new(NpmFetchResolver::new(deps_file_fetcher));
+  let npm_resolver =
+    Arc::new(NpmFetchResolver::new(deps_file_fetcher, npmrc.clone()));
 
   let mut selected_packages = Vec::with_capacity(add_flags.packages.len());
   let mut package_reqs = Vec::with_capacity(add_flags.packages.len());
 
   for entry_text in add_flags.packages.iter() {
-    let req = AddPackageReq::parse(entry_text).with_context(|| {
+    let req = AddRmPackageReq::parse(entry_text).with_context(|| {
       format!("Failed to parse package required: {}", entry_text)
     })?;
 
@@ -531,7 +479,7 @@ pub async fn add(
       selected_package.selected_version
     );
 
-    if selected_package.package_name.starts_with("npm:") {
+    if selected_package.package_name.starts_with("npm:") && prefer_npm_config {
       if let Some(npm) = &mut npm_config {
         npm.add(selected_package, dev);
       } else {
@@ -544,18 +492,11 @@ pub async fn add(
     }
   }
 
-  let mut commit_futures = vec![];
   if let Some(npm) = npm_config {
-    commit_futures.push(npm.commit());
+    npm.commit()?;
   }
   if let Some(deno) = deno_config {
-    commit_futures.push(deno.commit());
-  }
-  let commit_futures =
-    deno_core::futures::future::join_all(commit_futures).await;
-
-  for result in commit_futures {
-    result.context("Failed to update configuration file")?;
+    deno.commit()?;
   }
 
   npm_install_after_modification(flags, Some(jsr_resolver)).await?;
@@ -582,10 +523,10 @@ enum PackageAndVersion {
 async fn find_package_and_select_version_for_req(
   jsr_resolver: Arc<JsrFetchResolver>,
   npm_resolver: Arc<NpmFetchResolver>,
-  add_package_req: AddPackageReq,
+  add_package_req: AddRmPackageReq,
 ) -> Result<PackageAndVersion, AnyError> {
   match add_package_req.value {
-    AddPackageReqValue::Jsr(req) => {
+    AddRmPackageReqValue::Jsr(req) => {
       let jsr_prefixed_name = format!("jsr:{}", &req.name);
       let Some(nv) = jsr_resolver.req_to_nv(&req).await else {
         if npm_resolver.req_to_nv(&req).await.is_some() {
@@ -603,9 +544,11 @@ async fn find_package_and_select_version_for_req(
         });
       };
       let range_symbol = if req.version_req.version_text().starts_with('~') {
-        '~'
+        "~"
+      } else if req.version_req.version_text() == nv.version.to_string() {
+        ""
       } else {
-        '^'
+        "^"
       };
       Ok(PackageAndVersion::Selected(SelectedPackage {
         import_name: add_package_req.alias,
@@ -614,7 +557,7 @@ async fn find_package_and_select_version_for_req(
         selected_version: nv.version.to_string(),
       }))
     }
-    AddPackageReqValue::Npm(req) => {
+    AddRmPackageReqValue::Npm(req) => {
       let npm_prefixed_name = format!("npm:{}", &req.name);
       let Some(nv) = npm_resolver.req_to_nv(&req).await else {
         return Ok(PackageAndVersion::NotFound {
@@ -623,11 +566,15 @@ async fn find_package_and_select_version_for_req(
           package_req: req,
         });
       };
+
       let range_symbol = if req.version_req.version_text().starts_with('~') {
-        '~'
+        "~"
+      } else if req.version_req.version_text() == nv.version.to_string() {
+        ""
       } else {
-        '^'
+        "^"
       };
+
       Ok(PackageAndVersion::Selected(SelectedPackage {
         import_name: add_package_req.alias,
         package_name: npm_prefixed_name,
@@ -639,18 +586,18 @@ async fn find_package_and_select_version_for_req(
 }
 
 #[derive(Debug, PartialEq, Eq)]
-enum AddPackageReqValue {
+enum AddRmPackageReqValue {
   Jsr(PackageReq),
   Npm(PackageReq),
 }
 
 #[derive(Debug, PartialEq, Eq)]
-struct AddPackageReq {
+struct AddRmPackageReq {
   alias: String,
-  value: AddPackageReqValue,
+  value: AddRmPackageReqValue,
 }
 
-impl AddPackageReq {
+impl AddRmPackageReq {
   pub fn parse(entry_text: &str) -> Result<Result<Self, PackageReq>, AnyError> {
     enum Prefix {
       Jsr,
@@ -705,9 +652,9 @@ impl AddPackageReq {
         let req_ref =
           JsrPackageReqReference::from_str(&format!("jsr:{}", entry_text))?;
         let package_req = req_ref.into_inner().req;
-        Ok(Ok(AddPackageReq {
+        Ok(Ok(AddRmPackageReq {
           alias: maybe_alias.unwrap_or_else(|| package_req.name.to_string()),
-          value: AddPackageReqValue::Jsr(package_req),
+          value: AddRmPackageReqValue::Jsr(package_req),
         }))
       }
       Prefix::Npm => {
@@ -725,49 +672,48 @@ impl AddPackageReq {
             deno_semver::RangeSetOrTag::Tag("latest".into()),
           );
         }
-        Ok(Ok(AddPackageReq {
+        Ok(Ok(AddRmPackageReq {
           alias: maybe_alias.unwrap_or_else(|| package_req.name.to_string()),
-          value: AddPackageReqValue::Npm(package_req),
+          value: AddRmPackageReqValue::Npm(package_req),
         }))
       }
     }
   }
 }
 
-fn generate_imports(mut packages_to_version: Vec<(String, String)>) -> String {
-  packages_to_version.sort_by(|(k1, _), (k2, _)| k1.cmp(k2));
-  let mut contents = vec![];
-  let len = packages_to_version.len();
-  for (index, (package, version)) in packages_to_version.iter().enumerate() {
-    // TODO(bartlomieju): fix it, once we start support specifying version on the cli
-    contents.push(format!("\"{}\": \"{}\"", package, version));
-    if index != len - 1 {
-      contents.push(",".to_string());
-    }
-  }
-  contents.join("\n")
-}
-
 pub async fn remove(
   flags: Arc<Flags>,
   remove_flags: RemoveFlags,
 ) -> Result<(), AnyError> {
-  let (_, npm_config, deno_config) = load_configs(&flags)?;
+  let (_, npm_config, deno_config) = load_configs(&flags, || false)?;
 
-  let mut configs = [
-    ConfigUpdater::maybe_new(npm_config).await?,
-    ConfigUpdater::maybe_new(deno_config).await?,
-  ];
+  let mut configs = [npm_config, deno_config];
 
   let mut removed_packages = vec![];
 
   for package in &remove_flags.packages {
-    let mut removed = false;
+    let req = AddRmPackageReq::parse(package).with_context(|| {
+      format!("Failed to parse package required: {}", package)
+    })?;
+    let mut parsed_pkg_name = None;
     for config in configs.iter_mut().flatten() {
-      removed |= config.remove(package);
+      match &req {
+        Ok(rm_pkg) => {
+          if config.remove(&rm_pkg.alias) && parsed_pkg_name.is_none() {
+            parsed_pkg_name = Some(rm_pkg.alias.clone());
+          }
+        }
+        Err(pkg) => {
+          // An alias or a package name without registry/version
+          // constraints. Try to remove the package anyway.
+          if config.remove(&pkg.name) && parsed_pkg_name.is_none() {
+            parsed_pkg_name = Some(pkg.name.clone());
+          }
+        }
+      }
     }
-    if removed {
-      removed_packages.push(package.clone());
+    if let Some(pkg) = parsed_pkg_name {
+      removed_packages.push(pkg);
     }
   }
 
@@ -778,7 +724,7 @@ pub async fn remove(
       log::info!("Removed {}", crate::colors::green(package));
     }
     for config in configs.into_iter().flatten() {
-      config.commit().await?;
+      config.commit()?;
     }
 
     npm_install_after_modification(flags, None).await?;
@@ -805,88 +751,11 @@ async fn npm_install_after_modification(
   // npm install
   cache_deps::cache_top_level_deps(&cli_factory, jsr_resolver).await?;
 
-  Ok(())
-}
-
-fn update_config_file_content<
-  I: IntoIterator<Item = (&'static str, Option<String>)>,
->(
-  obj: &jsonc_parser::ast::Object,
-  config_file_contents: &str,
-  fmt_options: FmtOptionsConfig,
-  entries: I,
-  file_name: &str,
-) -> String {
-  let mut text_changes = vec![];
-  for (key, value) in entries {
-    match obj.properties.iter().enumerate().find_map(|(idx, k)| {
-      if k.name.as_str() == key {
-        Some((idx, k))
-      } else {
-        None
-      }
-    }) {
-      Some((
-        idx,
-        ObjectProp {
-          value: Value::Object(lit),
-          range,
-          ..
-        },
-      )) => {
-        if let Some(value) = value {
-          text_changes.push(TextChange {
-            range: (lit.range.start + 1)..(lit.range.end - 1),
-            new_text: value,
-          })
-        } else {
-          text_changes.push(TextChange {
-            // remove field entirely, making sure to
-            // remove the comma if it's not the last field
-            range: range.start..(if idx == obj.properties.len() - 1 {
-              range.end
-            } else {
-              obj.properties[idx + 1].range.start
-            }),
-            new_text: "".to_string(),
-          })
-        }
-      }
-
-      // need to add field
-      None => {
-        if let Some(value) = value {
-          let insert_position = obj.range.end - 1;
-          text_changes.push(TextChange {
-            range: insert_position..insert_position,
-            // NOTE(bartlomieju): adding `\n` here to force the formatter to always
-            // produce a config file that is multiline, like so:
-            // ```
-            // {
-            //   "imports": {
-            //     "<package_name>": "<registry>:<package_name>@<semver>"
-            //   }
-            // }
-            new_text: format!("\"{key}\": {{\n {value} }}"),
-          })
-        }
-      }
-      // we verified the shape of `imports`/`dependencies` above
-      Some(_) => unreachable!(),
-    }
+  if let Some(lockfile) = cli_factory.cli_options()?.maybe_lockfile() {
+    lockfile.write_if_changed()?;
   }
 
-  let new_text =
-    deno_ast::apply_text_changes(config_file_contents, text_changes);
-
-  crate::tools::fmt::format_json(
-    &PathBuf::from(file_name),
-    &new_text,
-    &fmt_options,
-  )
-  .ok()
-  .map(|formatted_text| formatted_text.unwrap_or_else(|| new_text.clone()))
-  .unwrap_or(new_text)
+  Ok(())
 }
 
 #[cfg(test)]
@@ -896,48 +765,52 @@ mod test {
   #[test]
   fn test_parse_add_package_req() {
     assert_eq!(
-      AddPackageReq::parse("jsr:foo").unwrap().unwrap(),
-      AddPackageReq {
+      AddRmPackageReq::parse("jsr:foo").unwrap().unwrap(),
+      AddRmPackageReq {
         alias: "foo".to_string(),
-        value: AddPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
+        value: AddRmPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
       }
     );
     assert_eq!(
-      AddPackageReq::parse("alias@jsr:foo").unwrap().unwrap(),
-      AddPackageReq {
+      AddRmPackageReq::parse("alias@jsr:foo").unwrap().unwrap(),
+      AddRmPackageReq {
         alias: "alias".to_string(),
-        value: AddPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
+        value: AddRmPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
       }
     );
     assert_eq!(
-      AddPackageReq::parse("@alias/pkg@npm:foo").unwrap().unwrap(),
-      AddPackageReq {
+      AddRmPackageReq::parse("@alias/pkg@npm:foo")
+        .unwrap()
+        .unwrap(),
+      AddRmPackageReq {
         alias: "@alias/pkg".to_string(),
-        value: AddPackageReqValue::Npm(
+        value: AddRmPackageReqValue::Npm(
           PackageReq::from_str("foo@latest").unwrap()
         )
       }
     );
     assert_eq!(
-      AddPackageReq::parse("@alias/pkg@jsr:foo").unwrap().unwrap(),
-      AddPackageReq {
+      AddRmPackageReq::parse("@alias/pkg@jsr:foo")
+        .unwrap()
+        .unwrap(),
+      AddRmPackageReq {
         alias: "@alias/pkg".to_string(),
-        value: AddPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
+        value: AddRmPackageReqValue::Jsr(PackageReq::from_str("foo").unwrap())
       }
     );
     assert_eq!(
-      AddPackageReq::parse("alias@jsr:foo@^1.5.0")
+      AddRmPackageReq::parse("alias@jsr:foo@^1.5.0")
         .unwrap()
         .unwrap(),
-      AddPackageReq {
+      AddRmPackageReq {
         alias: "alias".to_string(),
-        value: AddPackageReqValue::Jsr(
+        value: AddRmPackageReqValue::Jsr(
           PackageReq::from_str("foo@^1.5.0").unwrap()
         )
       }
     );
     assert_eq!(
-      AddPackageReq::parse("@scope/pkg@tag")
+      AddRmPackageReq::parse("@scope/pkg@tag")
         .unwrap()
         .unwrap_err()
         .to_string(),
diff --git a/cli/tools/registry/pm/cache_deps.rs b/cli/tools/registry/pm/cache_deps.rs
index c8258e6009..365622d11f 100644
--- a/cli/tools/registry/pm/cache_deps.rs
+++ b/cli/tools/registry/pm/cache_deps.rs
@@ -75,6 +75,13 @@ pub async fn cache_top_level_deps(
           if entry.key.ends_with('/') && specifier.as_str().ends_with('/') {
             continue;
           }
+          if specifier.scheme() == "file" {
+            if let Ok(path) = specifier.to_file_path() {
+              if !path.is_file() {
+                continue;
+              }
+            }
+          }
           roots.push(specifier.clone());
         }
       }
@@ -82,10 +89,6 @@ pub async fn cache_top_level_deps(
 
     while let Some(info_future) = info_futures.next().await {
       if let Some((specifier, info)) = info_future {
-        if info.export(".").is_some() {
-          roots.push(specifier.clone());
-          continue;
-        }
         let exports = info.exports();
         for (k, _) in exports {
           if let Ok(spec) = specifier.join(k) {
diff --git a/cli/tools/registry/tar.rs b/cli/tools/registry/tar.rs
index aca125e00b..6d1801ce69 100644
--- a/cli/tools/registry/tar.rs
+++ b/cli/tools/registry/tar.rs
@@ -120,7 +120,7 @@ fn resolve_content_maybe_unfurling(
         | MediaType::Unknown
         | MediaType::Json
         | MediaType::Wasm
-        | MediaType::TsBuildInfo => {
+        | MediaType::Css => {
           // not unfurlable data
           return Ok(data);
         }
diff --git a/cli/tools/repl/session.rs b/cli/tools/repl/session.rs
index 484664dae4..23b0f11ac5 100644
--- a/cli/tools/repl/session.rs
+++ b/cli/tools/repl/session.rs
@@ -25,6 +25,7 @@ use deno_ast::swc::visit::noop_visit_type;
 use deno_ast::swc::visit::Visit;
 use deno_ast::swc::visit::VisitWith;
 use deno_ast::ImportsNotUsedAsValues;
+use deno_ast::ModuleKind;
 use deno_ast::ModuleSpecifier;
 use deno_ast::ParseDiagnosticsError;
 use deno_ast::ParsedSource;
@@ -641,6 +642,10 @@ impl ReplSession {
           jsx_fragment_factory: self.jsx.frag_factory.clone(),
           jsx_import_source: self.jsx.import_source.clone(),
           var_decl_imports: true,
+          verbatim_module_syntax: false,
+        },
+        &deno_ast::TranspileModuleOptions {
+          module_kind: Some(ModuleKind::Esm),
         },
         &deno_ast::EmitOptions {
           source_map: deno_ast::SourceMapOption::None,
@@ -651,7 +656,6 @@ impl ReplSession {
         },
       )?
       .into_source()
-      .into_string()?
       .text;
 
     let value = self
diff --git a/cli/tools/run/hmr.rs b/cli/tools/run/hmr.rs
index 6ccf8e344b..6cebedd012 100644
--- a/cli/tools/run/hmr.rs
+++ b/cli/tools/run/hmr.rs
@@ -1,9 +1,11 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use crate::cdp;
-use crate::emit::Emitter;
-use crate::util::file_watcher::WatcherCommunicator;
-use crate::util::file_watcher::WatcherRestartMode;
+use std::collections::HashMap;
+use std::path::PathBuf;
+use std::sync::Arc;
+
+use deno_ast::MediaType;
+use deno_ast::ModuleKind;
 use deno_core::error::generic_error;
 use deno_core::error::AnyError;
 use deno_core::futures::StreamExt;
@@ -12,11 +14,14 @@ use deno_core::serde_json::{self};
 use deno_core::url::Url;
 use deno_core::LocalInspectorSession;
 use deno_terminal::colors;
-use std::collections::HashMap;
-use std::path::PathBuf;
-use std::sync::Arc;
 use tokio::select;
 
+use crate::cdp;
+use crate::emit::Emitter;
+use crate::resolver::CjsTracker;
+use crate::util::file_watcher::WatcherCommunicator;
+use crate::util::file_watcher::WatcherRestartMode;
+
 fn explain(status: &cdp::Status) -> &'static str {
   match status {
     cdp::Status::Ok => "OK",
@@ -58,6 +63,7 @@ pub struct HmrRunner {
   session: LocalInspectorSession,
   watcher_communicator: Arc<WatcherCommunicator>,
   script_ids: HashMap<String, String>,
+  cjs_tracker: Arc<CjsTracker>,
   emitter: Arc<Emitter>,
 }
 
@@ -139,7 +145,8 @@ impl crate::worker::HmrRunner for HmrRunner {
             };
 
             let source_code = self.emitter.load_and_emit_for_hmr(
-              &module_url
+              &module_url,
+              ModuleKind::from_is_cjs(self.cjs_tracker.is_maybe_cjs(&module_url, MediaType::from_specifier(&module_url))?),
             ).await?;
 
             let mut tries = 1;
@@ -172,12 +179,14 @@ impl crate::worker::HmrRunner for HmrRunner {
 
 impl HmrRunner {
   pub fn new(
+    cjs_tracker: Arc<CjsTracker>,
     emitter: Arc<Emitter>,
     session: LocalInspectorSession,
     watcher_communicator: Arc<WatcherCommunicator>,
   ) -> Self {
     Self {
       session,
+      cjs_tracker,
       emitter,
       watcher_communicator,
       script_ids: HashMap::new(),
diff --git a/cli/tools/run/mod.rs b/cli/tools/run/mod.rs
index 152e2650bd..bebb3f5881 100644
--- a/cli/tools/run/mod.rs
+++ b/cli/tools/run/mod.rs
@@ -30,6 +30,16 @@ To grant permissions, set them before the script argument. For example:
   }
 }
 
+fn set_npm_user_agent() {
+  static ONCE: std::sync::Once = std::sync::Once::new();
+  ONCE.call_once(|| {
+    std::env::set_var(
+      crate::npm::NPM_CONFIG_USER_AGENT_ENV_VAR,
+      crate::npm::get_npm_config_user_agent(),
+    );
+  });
+}
+
 pub async fn run_script(
   mode: WorkerExecutionMode,
   flags: Arc<Flags>,
@@ -58,6 +68,10 @@ pub async fn run_script(
 
   let main_module = cli_options.resolve_main_module()?;
 
+  if main_module.scheme() == "npm" {
+    set_npm_user_agent();
+  }
+
   maybe_npm_install(&factory).await?;
 
   let worker_factory = factory.create_cli_main_worker_factory().await?;
@@ -119,6 +133,10 @@ async fn run_with_watch(
         let cli_options = factory.cli_options()?;
         let main_module = cli_options.resolve_main_module()?;
 
+        if main_module.scheme() == "npm" {
+          set_npm_user_agent();
+        }
+
         maybe_npm_install(&factory).await?;
 
         let _ = watcher_communicator.watch_paths(cli_options.watch_paths());
diff --git a/cli/tools/serve.rs b/cli/tools/serve.rs
index 4ce1cad6f2..e3f9e94f8e 100644
--- a/cli/tools/serve.rs
+++ b/cli/tools/serve.rs
@@ -44,12 +44,15 @@ pub async fn serve(
   maybe_npm_install(&factory).await?;
 
   let worker_factory = factory.create_cli_main_worker_factory().await?;
-
+  let hmr = serve_flags
+    .watch
+    .map(|watch_flags| watch_flags.hmr)
+    .unwrap_or(false);
   do_serve(
     worker_factory,
     main_module.clone(),
     serve_flags.worker_count,
-    false,
+    hmr,
   )
   .await
 }
@@ -109,8 +112,6 @@ async fn do_serve(
     }
   }
   Ok(exit_code)
-
-  // main.await?
 }
 
 async fn run_worker(
@@ -119,7 +120,7 @@ async fn run_worker(
   main_module: ModuleSpecifier,
   hmr: bool,
 ) -> Result<i32, AnyError> {
-  let mut worker = worker_factory
+  let mut worker: crate::worker::CliMainWorker = worker_factory
     .create_main_worker(
       deno_runtime::WorkerExecutionMode::Serve {
         is_main: false,
diff --git a/cli/tools/task.rs b/cli/tools/task.rs
index 464b65d984..502b09d2c2 100644
--- a/cli/tools/task.rs
+++ b/cli/tools/task.rs
@@ -182,17 +182,21 @@ async fn run_task(opts: RunTaskOptions<'_>) -> Result<i32, AnyError> {
     &task_runner::get_script_with_args(script, cli_options.argv()),
   );
 
-  task_runner::run_task(task_runner::RunTaskOptions {
-    task_name,
-    script,
-    cwd,
-    env_vars,
-    custom_commands,
-    init_cwd: opts.cli_options.initial_cwd(),
-    argv: cli_options.argv(),
-    root_node_modules_dir: npm_resolver.root_node_modules_path(),
-  })
-  .await
+  Ok(
+    task_runner::run_task(task_runner::RunTaskOptions {
+      task_name,
+      script,
+      cwd,
+      env_vars,
+      custom_commands,
+      init_cwd: opts.cli_options.initial_cwd(),
+      argv: cli_options.argv(),
+      root_node_modules_dir: npm_resolver.root_node_modules_path(),
+      stdio: None,
+    })
+    .await?
+    .exit_code,
+  )
 }
 
 fn output_task(task_name: &str, script: &str) {
diff --git a/cli/tools/test/mod.rs b/cli/tools/test/mod.rs
index e81abad0b2..fa849614fa 100644
--- a/cli/tools/test/mod.rs
+++ b/cli/tools/test/mod.rs
@@ -631,7 +631,7 @@ async fn configure_main_worker(
       "Deno[Deno.internal].core.setLeakTracingEnabled(true);",
     )?;
   }
-  let res = worker.execute_side_module_possibly_with_npm().await;
+  let res = worker.execute_side_module().await;
   let mut worker = worker.into_main_worker();
   match res {
     Ok(()) => Ok(()),
diff --git a/cli/tools/upgrade.rs b/cli/tools/upgrade.rs
index 7f21e6649c..77a9f72b80 100644
--- a/cli/tools/upgrade.rs
+++ b/cli/tools/upgrade.rs
@@ -579,6 +579,10 @@ pub async fn upgrade(
 
   let output_exe_path =
     full_path_output_flag.as_ref().unwrap_or(&current_exe_path);
+
+  #[cfg(windows)]
+  kill_running_deno_lsp_processes();
+
   let output_result = if *output_exe_path == current_exe_path {
     replace_exe(&new_exe_path, output_exe_path)
   } else {
@@ -913,7 +917,7 @@ async fn download_package(
   // text above which will stay alive after the progress bars are complete
   let progress = progress_bar.update("");
   let maybe_bytes = client
-    .download_with_progress(download_url.clone(), None, &progress)
+    .download_with_progress_and_retries(download_url.clone(), None, &progress)
     .await
     .with_context(|| format!("Failed downloading {download_url}. The version you requested may not have been built for the current architecture."))?;
   Ok(maybe_bytes)
@@ -966,6 +970,34 @@ fn check_windows_access_denied_error(
   })
 }
 
+#[cfg(windows)]
+fn kill_running_deno_lsp_processes() {
+  // limit this to `deno lsp` invocations to avoid killing important programs someone might be running
+  let is_debug = log::log_enabled!(log::Level::Debug);
+  let get_pipe = || {
+    if is_debug {
+      std::process::Stdio::inherit()
+    } else {
+      std::process::Stdio::null()
+    }
+  };
+  let _ = Command::new("powershell.exe")
+    .args([
+      "-Command",
+      r#"Get-WmiObject Win32_Process | Where-Object {
+    $_.Name -eq 'deno.exe' -and
+    $_.CommandLine -match '^(?:\"[^\"]+\"|\S+)\s+lsp\b'
+} | ForEach-Object {
+  if ($_.Terminate()) {
+    Write-Host 'Terminated:' $_.ProcessId
+  }
+}"#,
+    ])
+    .stdout(get_pipe())
+    .stderr(get_pipe())
+    .output();
+}
+
 fn set_exe_permissions(
   current_exe_path: &Path,
   output_exe_path: &Path,
diff --git a/cli/tsc/99_main_compiler.js b/cli/tsc/99_main_compiler.js
index 719f2b9824..bdc4340e33 100644
--- a/cli/tsc/99_main_compiler.js
+++ b/cli/tsc/99_main_compiler.js
@@ -516,7 +516,6 @@ delete Object.prototype.__proto__;
   /** @typedef {{
    *    ls: ts.LanguageService & { [k:string]: any },
    *    compilerOptions: ts.CompilerOptions,
-   *    forceEnabledVerbatimModuleSyntax: boolean,
    *  }} LanguageServiceEntry */
   /** @type {{ unscoped: LanguageServiceEntry, byScope: Map<string, LanguageServiceEntry> }} */
   const languageServiceEntries = {
@@ -846,6 +845,8 @@ delete Object.prototype.__proto__;
         jqueryMessage,
       "Cannot_find_name_0_Do_you_need_to_install_type_definitions_for_jQuery_Try_npm_i_save_dev_types_Slash_2592":
         jqueryMessage,
+      "Module_0_was_resolved_to_1_but_allowArbitraryExtensions_is_not_set_6263":
+        "Module '{0}' was resolved to '{1}', but importing these modules is not supported.",
     };
   })());
 
@@ -1026,7 +1027,7 @@ delete Object.prototype.__proto__;
         : ts.sortAndDeduplicateDiagnostics(
           checkFiles.map((s) => program.getSemanticDiagnostics(s)).flat(),
         )),
-    ].filter(filterMapDiagnostic.bind(null, false));
+    ].filter(filterMapDiagnostic);
 
     // emit the tsbuildinfo file
     // @ts-ignore: emitBuildInfo is not exposed (https://github.com/microsoft/TypeScript/issues/49871)
@@ -1041,28 +1042,11 @@ delete Object.prototype.__proto__;
     debug("<<< exec stop");
   }
 
-  /**
-   * @param {boolean} isLsp
-   * @param {ts.Diagnostic} diagnostic
-   */
-  function filterMapDiagnostic(isLsp, diagnostic) {
+  /** @param {ts.Diagnostic} diagnostic */
+  function filterMapDiagnostic(diagnostic) {
     if (IGNORED_DIAGNOSTICS.includes(diagnostic.code)) {
       return false;
     }
-    if (isLsp) {
-      // TS1484: `...` is a type and must be imported using a type-only import when 'verbatimModuleSyntax' is enabled.
-      // We force-enable `verbatimModuleSyntax` in the LSP so the `type`
-      // modifier is used when auto-importing types. But we don't want this
-      // diagnostic unless it was explicitly enabled by the user.
-      if (diagnostic.code == 1484) {
-        const entry = (lastRequestScope
-          ? languageServiceEntries.byScope.get(lastRequestScope)
-          : null) ?? languageServiceEntries.unscoped;
-        if (entry.forceEnabledVerbatimModuleSyntax) {
-          return false;
-        }
-      }
-    }
     // make the diagnostic for using an `export =` in an es module a warning
     if (diagnostic.code === 1203) {
       diagnostic.category = ts.DiagnosticCategory.Warning;
@@ -1159,12 +1143,10 @@ delete Object.prototype.__proto__;
         "strict": true,
         "target": "esnext",
         "useDefineForClassFields": true,
-        "verbatimModuleSyntax": true,
         "jsx": "react",
         "jsxFactory": "React.createElement",
         "jsxFragmentFactory": "React.Fragment",
       }),
-      forceEnabledVerbatimModuleSyntax: true,
     };
     setLogDebug(enableDebugLogging, "TSLS");
     debug("serverInit()");
@@ -1230,17 +1212,8 @@ delete Object.prototype.__proto__;
           const ls = oldEntry
             ? oldEntry.ls
             : ts.createLanguageService(host, documentRegistry);
-          let forceEnabledVerbatimModuleSyntax = false;
-          if (!config["verbatimModuleSyntax"]) {
-            config["verbatimModuleSyntax"] = true;
-            forceEnabledVerbatimModuleSyntax = true;
-          }
           const compilerOptions = lspTsConfigToCompilerOptions(config);
-          newByScope.set(scope, {
-            ls,
-            compilerOptions,
-            forceEnabledVerbatimModuleSyntax,
-          });
+          newByScope.set(scope, { ls, compilerOptions });
           languageServiceEntries.byScope.delete(scope);
         }
         for (const oldEntry of languageServiceEntries.byScope.values()) {
@@ -1305,7 +1278,7 @@ delete Object.prototype.__proto__;
               ...ls.getSemanticDiagnostics(specifier),
               ...ls.getSuggestionDiagnostics(specifier),
               ...ls.getSyntacticDiagnostics(specifier),
-            ].filter(filterMapDiagnostic.bind(null, true)));
+            ].filter(filterMapDiagnostic));
           }
           return respond(id, diagnosticMap);
         } catch (e) {
@@ -1366,18 +1339,12 @@ delete Object.prototype.__proto__;
     "console",
     "Console",
     "ErrorConstructor",
-    "exports",
     "gc",
     "Global",
     "ImportMeta",
     "localStorage",
-    "module",
-    "NodeModule",
-    "NodeRequire",
-    "process",
     "queueMicrotask",
     "RequestInit",
-    "require",
     "ResponseInit",
     "sessionStorage",
     "setImmediate",
diff --git a/cli/tsc/diagnostics.rs b/cli/tsc/diagnostics.rs
index b0394ec177..d3795706eb 100644
--- a/cli/tsc/diagnostics.rs
+++ b/cli/tsc/diagnostics.rs
@@ -323,7 +323,7 @@ impl Diagnostics {
             // todo(dsherret): use a short lived cache to prevent parsing
             // source maps so often
             if let Ok(source_map) =
-              SourceMap::from_slice(&fast_check_module.source_map)
+              SourceMap::from_slice(fast_check_module.source_map.as_bytes())
             {
               if let Some(start) = d.start.as_mut() {
                 let maybe_token = source_map
diff --git a/cli/tsc/mod.rs b/cli/tsc/mod.rs
index 0e3387494a..dc7fc38f7a 100644
--- a/cli/tsc/mod.rs
+++ b/cli/tsc/mod.rs
@@ -3,8 +3,11 @@
 use crate::args::TsConfig;
 use crate::args::TypeCheckMode;
 use crate::cache::FastInsecureHasher;
+use crate::cache::ModuleInfoCache;
 use crate::node;
 use crate::npm::CliNpmResolver;
+use crate::npm::ResolvePkgFolderFromDenoReqError;
+use crate::resolver::CjsTracker;
 use crate::util::checksum;
 use crate::util::path::mapped_specifier_for_tsc;
 
@@ -31,12 +34,13 @@ use deno_graph::GraphKind;
 use deno_graph::Module;
 use deno_graph::ModuleGraph;
 use deno_graph::ResolutionResolved;
+use deno_runtime::deno_fs;
 use deno_runtime::deno_node::NodeResolver;
 use deno_semver::npm::NpmPackageReqReference;
 use node_resolver::errors::NodeJsErrorCode;
 use node_resolver::errors::NodeJsErrorCoded;
+use node_resolver::errors::PackageSubpathResolveError;
 use node_resolver::NodeModuleKind;
-use node_resolver::NodeResolution;
 use node_resolver::NodeResolutionMode;
 use once_cell::sync::Lazy;
 use std::borrow::Cow;
@@ -45,6 +49,7 @@ use std::fmt;
 use std::path::Path;
 use std::path::PathBuf;
 use std::sync::Arc;
+use thiserror::Error;
 
 mod diagnostics;
 
@@ -299,8 +304,76 @@ pub struct EmittedFile {
   pub media_type: MediaType,
 }
 
+pub fn into_specifier_and_media_type(
+  specifier: Option<ModuleSpecifier>,
+) -> (ModuleSpecifier, MediaType) {
+  match specifier {
+    Some(specifier) => {
+      let media_type = MediaType::from_specifier(&specifier);
+
+      (specifier, media_type)
+    }
+    None => (
+      Url::parse("internal:///missing_dependency.d.ts").unwrap(),
+      MediaType::Dts,
+    ),
+  }
+}
+
+#[derive(Debug)]
+pub struct TypeCheckingCjsTracker {
+  cjs_tracker: Arc<CjsTracker>,
+  module_info_cache: Arc<ModuleInfoCache>,
+}
+
+impl TypeCheckingCjsTracker {
+  pub fn new(
+    cjs_tracker: Arc<CjsTracker>,
+    module_info_cache: Arc<ModuleInfoCache>,
+  ) -> Self {
+    Self {
+      cjs_tracker,
+      module_info_cache,
+    }
+  }
+
+  pub fn is_cjs(
+    &self,
+    specifier: &ModuleSpecifier,
+    media_type: MediaType,
+    code: &Arc<str>,
+  ) -> bool {
+    if let Some(module_kind) =
+      self.cjs_tracker.get_known_kind(specifier, media_type)
+    {
+      module_kind.is_cjs()
+    } else {
+      let maybe_is_script = self
+        .module_info_cache
+        .as_module_analyzer()
+        .analyze_sync(specifier, media_type, code)
+        .ok()
+        .map(|info| info.is_script);
+      maybe_is_script
+        .and_then(|is_script| {
+          self
+            .cjs_tracker
+            .is_cjs_with_known_is_script(specifier, media_type, is_script)
+            .ok()
+        })
+        .unwrap_or_else(|| {
+          self
+            .cjs_tracker
+            .is_maybe_cjs(specifier, media_type)
+            .unwrap_or(false)
+        })
+    }
+  }
+}
+
 #[derive(Debug)]
 pub struct RequestNpmState {
+  pub cjs_tracker: Arc<TypeCheckingCjsTracker>,
   pub node_resolver: Arc<NodeResolver>,
   pub npm_resolver: Arc<dyn CliNpmResolver>,
 }
@@ -453,7 +526,7 @@ pub fn as_ts_script_kind(media_type: MediaType) -> i32 {
     MediaType::Tsx => 4,
     MediaType::Json => 6,
     MediaType::SourceMap
-    | MediaType::TsBuildInfo
+    | MediaType::Css
     | MediaType::Wasm
     | MediaType::Unknown => 0,
   }
@@ -486,25 +559,22 @@ fn op_load_inner(
 ) -> Result<Option<LoadResponse>, AnyError> {
   fn load_from_node_modules(
     specifier: &ModuleSpecifier,
-    node_resolver: Option<&NodeResolver>,
+    npm_state: Option<&RequestNpmState>,
     media_type: &mut MediaType,
     is_cjs: &mut bool,
   ) -> Result<String, AnyError> {
     *media_type = MediaType::from_specifier(specifier);
-    *is_cjs = node_resolver
-      .map(|node_resolver| {
-        match node_resolver.url_to_node_resolution(specifier.clone()) {
-          Ok(NodeResolution::CommonJs(_)) => true,
-          Ok(NodeResolution::Esm(_))
-          | Ok(NodeResolution::BuiltIn(_))
-          | Err(_) => false,
-        }
-      })
-      .unwrap_or(false);
     let file_path = specifier.to_file_path().unwrap();
     let code = std::fs::read_to_string(&file_path)
       .with_context(|| format!("Unable to load {}", file_path.display()))?;
-    Ok(code)
+    let code: Arc<str> = code.into();
+    *is_cjs = npm_state
+      .map(|npm_state| {
+        npm_state.cjs_tracker.is_cjs(specifier, *media_type, &code)
+      })
+      .unwrap_or(false);
+    // todo(dsherret): how to avoid cloning here?
+    Ok(code.to_string())
   }
 
   let state = state.borrow_mut::<State>();
@@ -557,6 +627,9 @@ fn op_load_inner(
       match module {
         Module::Js(module) => {
           media_type = module.media_type;
+          if matches!(media_type, MediaType::Cjs | MediaType::Cts) {
+            is_cjs = true;
+          }
           let source = module
             .fast_check_module()
             .map(|m| &*m.source)
@@ -570,11 +643,13 @@ fn op_load_inner(
         Module::Npm(_) | Module::Node(_) => None,
         Module::External(module) => {
           // means it's Deno code importing an npm module
-          let specifier =
-            node::resolve_specifier_into_node_modules(&module.specifier);
+          let specifier = node::resolve_specifier_into_node_modules(
+            &module.specifier,
+            &deno_fs::RealFs,
+          );
           Some(Cow::Owned(load_from_node_modules(
             &specifier,
-            state.maybe_npm.as_ref().map(|n| n.node_resolver.as_ref()),
+            state.maybe_npm.as_ref(),
             &mut media_type,
             &mut is_cjs,
           )?))
@@ -587,7 +662,7 @@ fn op_load_inner(
     {
       Some(Cow::Owned(load_from_node_modules(
         specifier,
-        Some(npm.node_resolver.as_ref()),
+        Some(npm),
         &mut media_type,
         &mut is_cjs,
       )?))
@@ -688,12 +763,30 @@ fn op_resolve_inner(
       Some(ResolutionResolved { specifier, .. }) => {
         resolve_graph_specifier_types(specifier, &referrer, state)?
       }
-      _ => resolve_non_graph_specifier_types(
-        &specifier,
-        &referrer,
-        referrer_kind,
-        state,
-      )?,
+      _ => {
+        match resolve_non_graph_specifier_types(
+          &specifier,
+          &referrer,
+          referrer_kind,
+          state,
+        ) {
+          Ok(maybe_result) => maybe_result,
+          Err(
+            err @ ResolveNonGraphSpecifierTypesError::ResolvePkgFolderFromDenoReq(
+              ResolvePkgFolderFromDenoReqError::Managed(_),
+            ),
+          ) => {
+            // it's most likely requesting the jsxImportSource, which isn't loaded
+            // into the graph when not using jsx, so just ignore this error
+            if specifier.ends_with("/jsx-runtime") {
+              None
+            } else {
+              return Err(err.into());
+            }
+          }
+          Err(err) => return Err(err.into()),
+        }
+      }
     };
     let result = match maybe_result {
       Some((specifier, media_type)) => {
@@ -718,7 +811,13 @@ fn op_resolve_inner(
             }
           }
         };
-        (specifier_str, media_type.as_ts_extension())
+        (
+          specifier_str,
+          match media_type {
+            MediaType::Css => ".js", // surface these as .js for typescript
+            media_type => media_type.as_ts_extension(),
+          },
+        )
       }
       None => (
         MISSING_DEPENDENCY_SPECIFIER.to_string(),
@@ -789,41 +888,50 @@ fn resolve_graph_specifier_types(
             Some(referrer),
             NodeResolutionMode::Types,
           );
-        let maybe_resolution = match res_result {
-          Ok(res) => Some(res),
+        let maybe_url = match res_result {
+          Ok(url) => Some(url),
           Err(err) => match err.code() {
             NodeJsErrorCode::ERR_TYPES_NOT_FOUND
             | NodeJsErrorCode::ERR_MODULE_NOT_FOUND => None,
             _ => return Err(err.into()),
           },
         };
-        Ok(Some(NodeResolution::into_specifier_and_media_type(
-          maybe_resolution,
-        )))
+        Ok(Some(into_specifier_and_media_type(maybe_url)))
       } else {
         Ok(None)
       }
     }
     Some(Module::External(module)) => {
       // we currently only use "External" for when the module is in an npm package
-      Ok(state.maybe_npm.as_ref().map(|npm| {
-        let specifier =
-          node::resolve_specifier_into_node_modules(&module.specifier);
-        NodeResolution::into_specifier_and_media_type(
-          npm.node_resolver.url_to_node_resolution(specifier).ok(),
-        )
+      Ok(state.maybe_npm.as_ref().map(|_| {
+        let specifier = node::resolve_specifier_into_node_modules(
+          &module.specifier,
+          &deno_fs::RealFs,
+        );
+        into_specifier_and_media_type(Some(specifier))
       }))
     }
     Some(Module::Node(_)) | None => Ok(None),
   }
 }
 
+#[derive(Debug, Error)]
+enum ResolveNonGraphSpecifierTypesError {
+  #[error(transparent)]
+  ResolvePkgFolderFromDenoReq(#[from] ResolvePkgFolderFromDenoReqError),
+  #[error(transparent)]
+  PackageSubpathResolve(#[from] PackageSubpathResolveError),
+}
+
 fn resolve_non_graph_specifier_types(
   raw_specifier: &str,
   referrer: &ModuleSpecifier,
   referrer_kind: NodeModuleKind,
   state: &State,
-) -> Result<Option<(ModuleSpecifier, MediaType)>, AnyError> {
+) -> Result<
+  Option<(ModuleSpecifier, MediaType)>,
+  ResolveNonGraphSpecifierTypesError,
+> {
   let npm = match state.maybe_npm.as_ref() {
     Some(npm) => npm,
     None => return Ok(None), // we only support non-graph types for npm packages
@@ -831,7 +939,7 @@ fn resolve_non_graph_specifier_types(
   let node_resolver = &npm.node_resolver;
   if node_resolver.in_npm_package(referrer) {
     // we're in an npm package, so use node resolution
-    Ok(Some(NodeResolution::into_specifier_and_media_type(
+    Ok(Some(into_specifier_and_media_type(
       node_resolver
         .resolve(
           raw_specifier,
@@ -839,7 +947,8 @@ fn resolve_non_graph_specifier_types(
           referrer_kind,
           NodeResolutionMode::Types,
         )
-        .ok(),
+        .ok()
+        .map(|res| res.into_url()),
     )))
   } else if let Ok(npm_req_ref) =
     NpmPackageReqReference::from_str(raw_specifier)
@@ -858,17 +967,15 @@ fn resolve_non_graph_specifier_types(
       Some(referrer),
       NodeResolutionMode::Types,
     );
-    let maybe_resolution = match res_result {
-      Ok(res) => Some(res),
+    let maybe_url = match res_result {
+      Ok(url) => Some(url),
       Err(err) => match err.code() {
         NodeJsErrorCode::ERR_TYPES_NOT_FOUND
         | NodeJsErrorCode::ERR_MODULE_NOT_FOUND => None,
         _ => return Err(err.into()),
       },
     };
-    Ok(Some(NodeResolution::into_specifier_and_media_type(
-      maybe_resolution,
-    )))
+    Ok(Some(into_specifier_and_media_type(maybe_url)))
   } else {
     Ok(None)
   }
diff --git a/cli/util/extract.rs b/cli/util/extract.rs
index 841cf6eb0f..f577cbefec 100644
--- a/cli/util/extract.rs
+++ b/cli/util/extract.rs
@@ -64,7 +64,7 @@ fn extract_inner(
   }) {
     Ok(parsed) => {
       let mut c = ExportCollector::default();
-      c.visit_program(parsed.program_ref());
+      c.visit_program(parsed.program().as_ref());
       c
     }
     Err(_) => ExportCollector::default(),
@@ -254,7 +254,11 @@ impl ExportCollector {
     let mut import_specifiers = vec![];
 
     if let Some(default_export) = &self.default_export {
-      if !symbols_to_exclude.contains(default_export) {
+      // If the default export conflicts with a named export, a named one
+      // takes precedence.
+      if !symbols_to_exclude.contains(default_export)
+        && !self.named_exports.contains(default_export)
+      {
         import_specifiers.push(ast::ImportSpecifier::Default(
           ast::ImportDefaultSpecifier {
             span: DUMMY_SP,
@@ -566,14 +570,14 @@ fn generate_pseudo_file(
   })?;
 
   let top_level_atoms = swc_utils::collect_decls_with_ctxt::<Atom, _>(
-    parsed.program_ref(),
+    &parsed.program_ref(),
     parsed.top_level_context(),
   );
 
   let transformed =
     parsed
       .program_ref()
-      .clone()
+      .to_owned()
       .fold_with(&mut as_folder(Transform {
         specifier: &file.specifier,
         base_file_specifier,
@@ -1137,6 +1141,30 @@ Deno.test("file:///README.md$6-12.js", async ()=>{
           media_type: MediaType::JavaScript,
         }],
       },
+      // https://github.com/denoland/deno/issues/26009
+      Test {
+        input: Input {
+          source: r#"
+/**
+ * ```ts
+ * console.log(Foo)
+ * ```
+ */
+export class Foo {}
+export default Foo
+"#,
+          specifier: "file:///main.ts",
+        },
+        expected: vec![Expected {
+          source: r#"import { Foo } from "file:///main.ts";
+Deno.test("file:///main.ts$3-6.ts", async ()=>{
+    console.log(Foo);
+});
+"#,
+          specifier: "file:///main.ts$3-6.ts",
+          media_type: MediaType::TypeScript,
+        }],
+      },
     ];
 
     for test in tests {
@@ -1326,6 +1354,28 @@ assertEquals(add(1, 2), 3);
           media_type: MediaType::JavaScript,
         }],
       },
+      // https://github.com/denoland/deno/issues/26009
+      Test {
+        input: Input {
+          source: r#"
+/**
+ * ```ts
+ * console.log(Foo)
+ * ```
+ */
+export class Foo {}
+export default Foo
+"#,
+          specifier: "file:///main.ts",
+        },
+        expected: vec![Expected {
+          source: r#"import { Foo } from "file:///main.ts";
+console.log(Foo);
+"#,
+          specifier: "file:///main.ts$3-6.ts",
+          media_type: MediaType::TypeScript,
+        }],
+      },
     ];
 
     for test in tests {
@@ -1366,7 +1416,7 @@ assertEquals(add(1, 2), 3);
       })
       .unwrap();
 
-      collector.visit_program(parsed.program_ref());
+      parsed.program_ref().visit_with(&mut collector);
       collector
     }
 
@@ -1581,6 +1631,16 @@ declare global {
         named_expected: atom_set!(),
         default_expected: None,
       },
+      // The identifier `Foo` conflicts, but `ExportCollector` doesn't do
+      // anything about it. It is handled by `to_import_specifiers` method.
+      Test {
+        input: r#"
+export class Foo {}
+export default Foo
+"#,
+        named_expected: atom_set!("Foo"),
+        default_expected: Some("Foo".into()),
+      },
     ];
 
     for test in tests {
diff --git a/cli/util/file_watcher.rs b/cli/util/file_watcher.rs
index d92d880bc1..8d734af88e 100644
--- a/cli/util/file_watcher.rs
+++ b/cli/util/file_watcher.rs
@@ -30,7 +30,7 @@ use tokio::sync::mpsc;
 use tokio::sync::mpsc::UnboundedReceiver;
 use tokio::time::sleep;
 
-const CLEAR_SCREEN: &str = "\x1B[2J\x1B[1;1H";
+const CLEAR_SCREEN: &str = "\x1B[H\x1B[2J\x1B[3J";
 const DEBOUNCE_INTERVAL: Duration = Duration::from_millis(200);
 
 struct DebouncedReceiver {
diff --git a/cli/util/fs.rs b/cli/util/fs.rs
index a021ec19c0..2c34f486ad 100644
--- a/cli/util/fs.rs
+++ b/cli/util/fs.rs
@@ -160,11 +160,11 @@ fn atomic_write_file(
     data: &[u8],
   ) -> std::io::Result<()> {
     fs.write_file(temp_file_path, data)?;
-    fs.rename_file(temp_file_path, file_path).map_err(|err| {
-      // clean up the created temp file on error
-      let _ = fs.remove_file(temp_file_path);
-      err
-    })
+    fs.rename_file(temp_file_path, file_path)
+      .inspect_err(|_err| {
+        // clean up the created temp file on error
+        let _ = fs.remove_file(temp_file_path);
+      })
   }
 
   let temp_file_path = get_atomic_file_path(file_path);
@@ -277,7 +277,7 @@ pub fn write_file_2<T: AsRef<[u8]>>(
 
 /// Similar to `std::fs::canonicalize()` but strips UNC prefixes on Windows.
 pub fn canonicalize_path(path: &Path) -> Result<PathBuf, Error> {
-  Ok(deno_core::strip_unc_prefix(path.canonicalize()?))
+  Ok(deno_path_util::strip_unc_prefix(path.canonicalize()?))
 }
 
 /// Canonicalizes a path which might be non-existent by going up the
diff --git a/cli/util/logger.rs b/cli/util/logger.rs
index cdc89411fe..d93753dfd3 100644
--- a/cli/util/logger.rs
+++ b/cli/util/logger.rs
@@ -65,6 +65,8 @@ pub fn init(maybe_level: Option<log::Level>) {
   .filter_module("swc_ecma_parser", log::LevelFilter::Error)
   // Suppress span lifecycle logs since they are too verbose
   .filter_module("tracing::span", log::LevelFilter::Off)
+  // for deno_compile, this is too verbose
+  .filter_module("editpe", log::LevelFilter::Error)
   .format(|buf, record| {
     let mut target = record.target().to_string();
     if let Some(line_no) = record.line() {
diff --git a/cli/util/mod.rs b/cli/util/mod.rs
index e59b09d2c7..f81a74c449 100644
--- a/cli/util/mod.rs
+++ b/cli/util/mod.rs
@@ -14,6 +14,7 @@ pub mod logger;
 pub mod path;
 pub mod progress_bar;
 pub mod result;
+pub mod retry;
 pub mod sync;
 pub mod text_encoding;
 pub mod unix;
diff --git a/cli/util/path.rs b/cli/util/path.rs
index e4ae6e7cb1..58bed664f9 100644
--- a/cli/util/path.rs
+++ b/cli/util/path.rs
@@ -42,21 +42,6 @@ pub fn get_extension(file_path: &Path) -> Option<String> {
     .map(|e| e.to_lowercase());
 }
 
-pub fn specifier_has_extension(
-  specifier: &ModuleSpecifier,
-  searching_ext: &str,
-) -> bool {
-  let Some((_, ext)) = specifier.path().rsplit_once('.') else {
-    return false;
-  };
-  let searching_ext = searching_ext.strip_prefix('.').unwrap_or(searching_ext);
-  debug_assert!(!searching_ext.contains('.')); // exts like .d.ts are not implemented here
-  if ext.len() != searching_ext.len() {
-    return false;
-  }
-  ext.eq_ignore_ascii_case(searching_ext)
-}
-
 pub fn get_atomic_dir_path(file_path: &Path) -> PathBuf {
   let rand = gen_rand_path_component();
   let new_file_name = format!(
@@ -350,18 +335,6 @@ mod test {
     }
   }
 
-  #[test]
-  fn test_specifier_has_extension() {
-    fn get(specifier: &str, ext: &str) -> bool {
-      specifier_has_extension(&ModuleSpecifier::parse(specifier).unwrap(), ext)
-    }
-
-    assert!(get("file:///a/b/c.ts", "ts"));
-    assert!(get("file:///a/b/c.ts", ".ts"));
-    assert!(!get("file:///a/b/c.ts", ".cts"));
-    assert!(get("file:///a/b/c.CtS", ".cts"));
-  }
-
   #[test]
   fn test_to_percent_decoded_str() {
     let str = to_percent_decoded_str("%F0%9F%A6%95");
diff --git a/cli/util/progress_bar/renderer.rs b/cli/util/progress_bar/renderer.rs
index a83ceb3334..6b08dada12 100644
--- a/cli/util/progress_bar/renderer.rs
+++ b/cli/util/progress_bar/renderer.rs
@@ -193,10 +193,16 @@ impl ProgressBarRenderer for TextOnlyProgressBarRenderer {
         }
       };
 
+      // TODO(@marvinhagemeister): We're trying to reconstruct the original
+      // specifier from the resolved one, but we lack the information about
+      // private registries URLs and other things here.
       let message = display_entry
         .message
         .replace("https://registry.npmjs.org/", "npm:")
-        .replace("https://jsr.io/", "jsr:");
+        .replace("https://jsr.io/", "jsr:")
+        .replace("%2f", "/")
+        .replace("%2F", "/");
+
       display_str.push_str(
         &colors::gray(format!(" - {}{}\n", message, bytes_text)).to_string(),
       );
diff --git a/cli/util/retry.rs b/cli/util/retry.rs
new file mode 100644
index 0000000000..a8febe60de
--- /dev/null
+++ b/cli/util/retry.rs
@@ -0,0 +1,41 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+use std::future::Future;
+use std::time::Duration;
+
+pub fn retry<
+  F: FnMut() -> Fut,
+  T,
+  E,
+  Fut: Future<Output = Result<T, E>>,
+  ShouldRetry: FnMut(&E) -> bool,
+>(
+  mut f: F,
+  mut should_retry: ShouldRetry,
+) -> impl Future<Output = Result<T, E>> {
+  const WAITS: [Duration; 3] = [
+    Duration::from_millis(100),
+    Duration::from_millis(250),
+    Duration::from_millis(500),
+  ];
+
+  let mut waits = WAITS.into_iter();
+  async move {
+    let mut first_result = None;
+    loop {
+      let result = f().await;
+      match result {
+        Ok(r) => return Ok(r),
+        Err(e) if !should_retry(&e) => return Err(e),
+        _ => {}
+      }
+      if first_result.is_none() {
+        first_result = Some(result);
+      }
+      let Some(wait) = waits.next() else {
+        return first_result.unwrap();
+      };
+      tokio::time::sleep(wait).await;
+    }
+  }
+}
diff --git a/cli/util/text_encoding.rs b/cli/util/text_encoding.rs
index d2e0832c95..8524e63ebb 100644
--- a/cli/util/text_encoding.rs
+++ b/cli/util/text_encoding.rs
@@ -1,6 +1,8 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use std::borrow::Cow;
 use std::ops::Range;
+use std::sync::Arc;
 
 use base64::prelude::BASE64_STANDARD;
 use base64::Engine;
@@ -9,6 +11,15 @@ use deno_core::ModuleSourceCode;
 static SOURCE_MAP_PREFIX: &[u8] =
   b"//# sourceMappingURL=data:application/json;base64,";
 
+pub fn from_utf8_lossy_owned(bytes: Vec<u8>) -> String {
+  match String::from_utf8_lossy(&bytes) {
+    Cow::Owned(code) => code,
+    // SAFETY: `String::from_utf8_lossy` guarantees that the result is valid
+    // UTF-8 if `Cow::Borrowed` is returned.
+    Cow::Borrowed(_) => unsafe { String::from_utf8_unchecked(bytes) },
+  }
+}
+
 pub fn source_map_from_code(code: &[u8]) -> Option<Vec<u8>> {
   let range = find_source_map_range(code)?;
   let source_map_range = &code[range];
@@ -85,6 +96,29 @@ fn find_source_map_range(code: &[u8]) -> Option<Range<usize>> {
   }
 }
 
+/// Converts an `Arc<str>` to an `Arc<[u8]>`.
+#[allow(dead_code)]
+pub fn arc_str_to_bytes(arc_str: Arc<str>) -> Arc<[u8]> {
+  let raw = Arc::into_raw(arc_str);
+  // SAFETY: This is safe because they have the same memory layout.
+  unsafe { Arc::from_raw(raw as *const [u8]) }
+}
+
+/// Converts an `Arc<u8>` to an `Arc<str>` if able.
+#[allow(dead_code)]
+pub fn arc_u8_to_arc_str(
+  arc_u8: Arc<[u8]>,
+) -> Result<Arc<str>, std::str::Utf8Error> {
+  // Check that the string is valid UTF-8.
+  std::str::from_utf8(&arc_u8)?;
+  // SAFETY: the string is valid UTF-8, and the layout Arc<[u8]> is the same as
+  // Arc<str>. This is proven by the From<Arc<str>> impl for Arc<[u8]> from the
+  // standard library.
+  Ok(unsafe {
+    std::mem::transmute::<std::sync::Arc<[u8]>, std::sync::Arc<str>>(arc_u8)
+  })
+}
+
 #[cfg(test)]
 mod tests {
   use std::sync::Arc;
diff --git a/cli/worker.rs b/cli/worker.rs
index cc18c0d154..baacd681a1 100644
--- a/cli/worker.rs
+++ b/cli/worker.rs
@@ -14,16 +14,17 @@ use deno_core::v8;
 use deno_core::CompiledWasmModuleStore;
 use deno_core::Extension;
 use deno_core::FeatureChecker;
-use deno_core::ModuleId;
 use deno_core::ModuleLoader;
 use deno_core::PollEventLoopOptions;
 use deno_core::SharedArrayBufferStore;
 use deno_runtime::code_cache;
 use deno_runtime::deno_broadcast_channel::InMemoryBroadcastChannel;
 use deno_runtime::deno_fs;
-use deno_runtime::deno_node;
 use deno_runtime::deno_node::NodeExtInitServices;
+use deno_runtime::deno_node::NodeRequireLoader;
+use deno_runtime::deno_node::NodeRequireLoaderRc;
 use deno_runtime::deno_node::NodeResolver;
+use deno_runtime::deno_node::PackageJsonResolver;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::deno_tls::RootCertStoreProvider;
 use deno_runtime::deno_web::BlobStore;
@@ -42,7 +43,6 @@ use deno_runtime::WorkerExecutionMode;
 use deno_runtime::WorkerLogLevel;
 use deno_semver::npm::NpmPackageReqReference;
 use deno_terminal::colors;
-use node_resolver::NodeResolution;
 use node_resolver::NodeResolutionMode;
 use tokio::select;
 
@@ -56,21 +56,22 @@ use crate::util::file_watcher::WatcherCommunicator;
 use crate::util::file_watcher::WatcherRestartMode;
 use crate::version;
 
-pub struct ModuleLoaderAndSourceMapGetter {
+pub struct CreateModuleLoaderResult {
   pub module_loader: Rc<dyn ModuleLoader>,
+  pub node_require_loader: Rc<dyn NodeRequireLoader>,
 }
 
 pub trait ModuleLoaderFactory: Send + Sync {
   fn create_for_main(
     &self,
     root_permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter;
+  ) -> CreateModuleLoaderResult;
 
   fn create_for_worker(
     &self,
     parent_permissions: PermissionsContainer,
     permissions: PermissionsContainer,
-  ) -> ModuleLoaderAndSourceMapGetter;
+  ) -> CreateModuleLoaderResult;
 }
 
 #[async_trait::async_trait(?Send)]
@@ -107,7 +108,6 @@ pub struct CliMainWorkerOptions {
   pub inspect_wait: bool,
   pub strace_ops: Option<Vec<String>>,
   pub is_inspecting: bool,
-  pub is_npm_main: bool,
   pub location: Option<Url>,
   pub argv0: Option<String>,
   pub node_debug: Option<String>,
@@ -135,6 +135,7 @@ struct SharedWorkerState {
   module_loader_factory: Box<dyn ModuleLoaderFactory>,
   node_resolver: Arc<NodeResolver>,
   npm_resolver: Arc<dyn CliNpmResolver>,
+  pkg_json_resolver: Arc<PackageJsonResolver>,
   root_cert_store_provider: Arc<dyn RootCertStoreProvider>,
   root_permissions: PermissionsContainer,
   shared_array_buffer_store: SharedArrayBufferStore,
@@ -144,11 +145,15 @@ struct SharedWorkerState {
 }
 
 impl SharedWorkerState {
-  pub fn create_node_init_services(&self) -> NodeExtInitServices {
+  pub fn create_node_init_services(
+    &self,
+    node_require_loader: NodeRequireLoaderRc,
+  ) -> NodeExtInitServices {
     NodeExtInitServices {
-      node_require_resolver: self.npm_resolver.clone().into_require_resolver(),
+      node_require_loader,
       node_resolver: self.node_resolver.clone(),
       npm_resolver: self.npm_resolver.clone().into_npm_resolver(),
+      pkg_json_resolver: self.pkg_json_resolver.clone(),
     }
   }
 
@@ -159,7 +164,6 @@ impl SharedWorkerState {
 
 pub struct CliMainWorker {
   main_module: ModuleSpecifier,
-  is_main_cjs: bool,
   worker: MainWorker,
   shared: Arc<SharedWorkerState>,
 }
@@ -181,17 +185,7 @@ impl CliMainWorker {
 
     log::debug!("main_module {}", self.main_module);
 
-    if self.is_main_cjs {
-      deno_node::load_cjs_module(
-        &mut self.worker.js_runtime,
-        &self.main_module.to_file_path().unwrap().to_string_lossy(),
-        true,
-        self.shared.options.inspect_brk,
-      )?;
-    } else {
-      self.execute_main_module_possibly_with_npm().await?;
-    }
-
+    self.execute_main_module().await?;
     self.worker.dispatch_load_event()?;
 
     loop {
@@ -279,22 +273,7 @@ impl CliMainWorker {
       /// Execute the given main module emitting load and unload events before and after execution
       /// respectively.
       pub async fn execute(&mut self) -> Result<(), AnyError> {
-        if self.inner.is_main_cjs {
-          deno_node::load_cjs_module(
-            &mut self.inner.worker.js_runtime,
-            &self
-              .inner
-              .main_module
-              .to_file_path()
-              .unwrap()
-              .to_string_lossy(),
-            true,
-            self.inner.shared.options.inspect_brk,
-          )?;
-        } else {
-          self.inner.execute_main_module_possibly_with_npm().await?;
-        }
-
+        self.inner.execute_main_module().await?;
         self.inner.worker.dispatch_load_event()?;
         self.pending_unload = true;
 
@@ -335,24 +314,13 @@ impl CliMainWorker {
     executor.execute().await
   }
 
-  pub async fn execute_main_module_possibly_with_npm(
-    &mut self,
-  ) -> Result<(), AnyError> {
+  pub async fn execute_main_module(&mut self) -> Result<(), AnyError> {
     let id = self.worker.preload_main_module(&self.main_module).await?;
-    self.evaluate_module_possibly_with_npm(id).await
+    self.worker.evaluate_module(id).await
   }
 
-  pub async fn execute_side_module_possibly_with_npm(
-    &mut self,
-  ) -> Result<(), AnyError> {
+  pub async fn execute_side_module(&mut self) -> Result<(), AnyError> {
     let id = self.worker.preload_side_module(&self.main_module).await?;
-    self.evaluate_module_possibly_with_npm(id).await
-  }
-
-  async fn evaluate_module_possibly_with_npm(
-    &mut self,
-    id: ModuleId,
-  ) -> Result<(), AnyError> {
     self.worker.evaluate_module(id).await
   }
 
@@ -431,6 +399,7 @@ impl CliMainWorkerFactory {
     module_loader_factory: Box<dyn ModuleLoaderFactory>,
     node_resolver: Arc<NodeResolver>,
     npm_resolver: Arc<dyn CliNpmResolver>,
+    pkg_json_resolver: Arc<PackageJsonResolver>,
     root_cert_store_provider: Arc<dyn RootCertStoreProvider>,
     root_permissions: PermissionsContainer,
     storage_key_resolver: StorageKeyResolver,
@@ -451,6 +420,7 @@ impl CliMainWorkerFactory {
         module_loader_factory,
         node_resolver,
         npm_resolver,
+        pkg_json_resolver,
         root_cert_store_provider,
         root_permissions,
         shared_array_buffer_store: Default::default(),
@@ -486,7 +456,13 @@ impl CliMainWorkerFactory {
     stdio: deno_runtime::deno_io::Stdio,
   ) -> Result<CliMainWorker, AnyError> {
     let shared = &self.shared;
-    let (main_module, is_main_cjs) = if let Ok(package_ref) =
+    let CreateModuleLoaderResult {
+      module_loader,
+      node_require_loader,
+    } = shared
+      .module_loader_factory
+      .create_for_main(permissions.clone());
+    let main_module = if let Ok(package_ref) =
       NpmPackageReqReference::from_specifier(&main_module)
     {
       if let Some(npm_resolver) = shared.npm_resolver.as_managed() {
@@ -506,9 +482,8 @@ impl CliMainWorkerFactory {
           package_ref.req(),
           &referrer,
         )?;
-      let node_resolution = self
+      let main_module = self
         .resolve_binary_entrypoint(&package_folder, package_ref.sub_path())?;
-      let is_main_cjs = matches!(node_resolution, NodeResolution::CommonJs(_));
 
       if let Some(lockfile) = &shared.maybe_lockfile {
         // For npm binary commands, ensure that the lockfile gets updated
@@ -517,22 +492,11 @@ impl CliMainWorkerFactory {
         lockfile.write_if_changed()?;
       }
 
-      (node_resolution.into_url(), is_main_cjs)
-    } else if shared.options.is_npm_main
-      || shared.node_resolver.in_npm_package(&main_module)
-    {
-      let node_resolution =
-        shared.node_resolver.url_to_node_resolution(main_module)?;
-      let is_main_cjs = matches!(node_resolution, NodeResolution::CommonJs(_));
-      (node_resolution.into_url(), is_main_cjs)
+      main_module
     } else {
-      let is_cjs = main_module.path().ends_with(".cjs");
-      (main_module, is_cjs)
+      main_module
     };
 
-    let ModuleLoaderAndSourceMapGetter { module_loader } = shared
-      .module_loader_factory
-      .create_for_main(permissions.clone());
     let maybe_inspector_server = shared.maybe_inspector_server.clone();
 
     let create_web_worker_cb =
@@ -572,7 +536,9 @@ impl CliMainWorkerFactory {
       root_cert_store_provider: Some(shared.root_cert_store_provider.clone()),
       module_loader,
       fs: shared.fs.clone(),
-      node_services: Some(shared.create_node_init_services()),
+      node_services: Some(
+        shared.create_node_init_services(node_require_loader),
+      ),
       npm_process_state_provider: Some(shared.npm_process_state_provider()),
       blob_store: shared.blob_store.clone(),
       broadcast_channel: shared.broadcast_channel.clone(),
@@ -657,7 +623,6 @@ impl CliMainWorkerFactory {
 
     Ok(CliMainWorker {
       main_module,
-      is_main_cjs,
       worker,
       shared: shared.clone(),
     })
@@ -667,19 +632,19 @@ impl CliMainWorkerFactory {
     &self,
     package_folder: &Path,
     sub_path: Option<&str>,
-  ) -> Result<NodeResolution, AnyError> {
+  ) -> Result<ModuleSpecifier, AnyError> {
     match self
       .shared
       .node_resolver
       .resolve_binary_export(package_folder, sub_path)
     {
-      Ok(node_resolution) => Ok(node_resolution),
+      Ok(specifier) => Ok(specifier),
       Err(original_err) => {
         // if the binary entrypoint was not found, fallback to regular node resolution
         let result =
           self.resolve_binary_entrypoint_fallback(package_folder, sub_path);
         match result {
-          Ok(Some(resolution)) => Ok(resolution),
+          Ok(Some(specifier)) => Ok(specifier),
           Ok(None) => Err(original_err.into()),
           Err(fallback_err) => {
             bail!("{:#}\n\nFallback failed: {:#}", original_err, fallback_err)
@@ -694,7 +659,7 @@ impl CliMainWorkerFactory {
     &self,
     package_folder: &Path,
     sub_path: Option<&str>,
-  ) -> Result<Option<NodeResolution>, AnyError> {
+  ) -> Result<Option<ModuleSpecifier>, AnyError> {
     // only fallback if the user specified a sub path
     if sub_path.is_none() {
       // it's confusing to users if the package doesn't have any binary
@@ -703,7 +668,7 @@ impl CliMainWorkerFactory {
       return Ok(None);
     }
 
-    let resolution = self
+    let specifier = self
       .shared
       .node_resolver
       .resolve_package_subpath_from_deno_module(
@@ -712,19 +677,14 @@ impl CliMainWorkerFactory {
         /* referrer */ None,
         NodeResolutionMode::Execution,
       )?;
-    match &resolution {
-      NodeResolution::BuiltIn(_) => Ok(None),
-      NodeResolution::CommonJs(specifier) | NodeResolution::Esm(specifier) => {
-        if specifier
-          .to_file_path()
-          .map(|p| p.exists())
-          .unwrap_or(false)
-        {
-          Ok(Some(resolution))
-        } else {
-          bail!("Cannot find module '{}'", specifier)
-        }
-      }
+    if specifier
+      .to_file_path()
+      .map(|p| p.exists())
+      .unwrap_or(false)
+    {
+      Ok(Some(specifier))
+    } else {
+      bail!("Cannot find module '{}'", specifier)
     }
   }
 }
@@ -736,11 +696,13 @@ fn create_web_worker_callback(
   Arc::new(move |args| {
     let maybe_inspector_server = shared.maybe_inspector_server.clone();
 
-    let ModuleLoaderAndSourceMapGetter { module_loader } =
-      shared.module_loader_factory.create_for_worker(
-        args.parent_permissions.clone(),
-        args.permissions.clone(),
-      );
+    let CreateModuleLoaderResult {
+      module_loader,
+      node_require_loader,
+    } = shared.module_loader_factory.create_for_worker(
+      args.parent_permissions.clone(),
+      args.permissions.clone(),
+    );
     let create_web_worker_cb =
       create_web_worker_callback(shared.clone(), stdio.clone());
 
@@ -770,7 +732,9 @@ fn create_web_worker_callback(
       root_cert_store_provider: Some(shared.root_cert_store_provider.clone()),
       module_loader,
       fs: shared.fs.clone(),
-      node_services: Some(shared.create_node_init_services()),
+      node_services: Some(
+        shared.create_node_init_services(node_require_loader),
+      ),
       blob_store: shared.blob_store.clone(),
       broadcast_channel: shared.broadcast_channel.clone(),
       shared_array_buffer_store: Some(shared.shared_array_buffer_store.clone()),
diff --git a/ext/broadcast_channel/Cargo.toml b/ext/broadcast_channel/Cargo.toml
index 3caf7b9efd..e6eeeed5ec 100644
--- a/ext/broadcast_channel/Cargo.toml
+++ b/ext/broadcast_channel/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_broadcast_channel"
-version = "0.165.0"
+version = "0.169.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -16,5 +16,6 @@ path = "lib.rs"
 [dependencies]
 async-trait.workspace = true
 deno_core.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
 uuid.workspace = true
diff --git a/ext/broadcast_channel/in_memory_broadcast_channel.rs b/ext/broadcast_channel/in_memory_broadcast_channel.rs
index 00b52a9d60..61dc68e17d 100644
--- a/ext/broadcast_channel/in_memory_broadcast_channel.rs
+++ b/ext/broadcast_channel/in_memory_broadcast_channel.rs
@@ -3,13 +3,13 @@
 use std::sync::Arc;
 
 use async_trait::async_trait;
-use deno_core::error::AnyError;
 use deno_core::parking_lot::Mutex;
 use tokio::sync::broadcast;
 use tokio::sync::mpsc;
 use uuid::Uuid;
 
 use crate::BroadcastChannel;
+use crate::BroadcastChannelError;
 
 #[derive(Clone)]
 pub struct InMemoryBroadcastChannel(Arc<Mutex<broadcast::Sender<Message>>>);
@@ -41,7 +41,7 @@ impl Default for InMemoryBroadcastChannel {
 impl BroadcastChannel for InMemoryBroadcastChannel {
   type Resource = InMemoryBroadcastChannelResource;
 
-  fn subscribe(&self) -> Result<Self::Resource, AnyError> {
+  fn subscribe(&self) -> Result<Self::Resource, BroadcastChannelError> {
     let (cancel_tx, cancel_rx) = mpsc::unbounded_channel();
     let broadcast_rx = self.0.lock().subscribe();
     let rx = tokio::sync::Mutex::new((broadcast_rx, cancel_rx));
@@ -53,7 +53,10 @@ impl BroadcastChannel for InMemoryBroadcastChannel {
     })
   }
 
-  fn unsubscribe(&self, resource: &Self::Resource) -> Result<(), AnyError> {
+  fn unsubscribe(
+    &self,
+    resource: &Self::Resource,
+  ) -> Result<(), BroadcastChannelError> {
     Ok(resource.cancel_tx.send(())?)
   }
 
@@ -62,7 +65,7 @@ impl BroadcastChannel for InMemoryBroadcastChannel {
     resource: &Self::Resource,
     name: String,
     data: Vec<u8>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), BroadcastChannelError> {
     let name = Arc::new(name);
     let data = Arc::new(data);
     let uuid = resource.uuid;
@@ -73,7 +76,7 @@ impl BroadcastChannel for InMemoryBroadcastChannel {
   async fn recv(
     &self,
     resource: &Self::Resource,
-  ) -> Result<Option<crate::Message>, AnyError> {
+  ) -> Result<Option<crate::Message>, BroadcastChannelError> {
     let mut g = resource.rx.lock().await;
     let (broadcast_rx, cancel_rx) = &mut *g;
     loop {
diff --git a/ext/broadcast_channel/lib.rs b/ext/broadcast_channel/lib.rs
index 47c48656d8..c1de118a36 100644
--- a/ext/broadcast_channel/lib.rs
+++ b/ext/broadcast_channel/lib.rs
@@ -10,34 +10,69 @@ use std::path::PathBuf;
 use std::rc::Rc;
 
 use async_trait::async_trait;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::JsBuffer;
 use deno_core::OpState;
 use deno_core::Resource;
 use deno_core::ResourceId;
+use tokio::sync::broadcast::error::SendError as BroadcastSendError;
+use tokio::sync::mpsc::error::SendError as MpscSendError;
 
 pub const UNSTABLE_FEATURE_NAME: &str = "broadcast-channel";
 
+#[derive(Debug, thiserror::Error)]
+pub enum BroadcastChannelError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  MPSCSendError(MpscSendError<Box<dyn std::fmt::Debug + Send + Sync>>),
+  #[error(transparent)]
+  BroadcastSendError(
+    BroadcastSendError<Box<dyn std::fmt::Debug + Send + Sync>>,
+  ),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
+impl<T: std::fmt::Debug + Send + Sync + 'static> From<MpscSendError<T>>
+  for BroadcastChannelError
+{
+  fn from(value: MpscSendError<T>) -> Self {
+    BroadcastChannelError::MPSCSendError(MpscSendError(Box::new(value.0)))
+  }
+}
+impl<T: std::fmt::Debug + Send + Sync + 'static> From<BroadcastSendError<T>>
+  for BroadcastChannelError
+{
+  fn from(value: BroadcastSendError<T>) -> Self {
+    BroadcastChannelError::BroadcastSendError(BroadcastSendError(Box::new(
+      value.0,
+    )))
+  }
+}
+
 #[async_trait]
 pub trait BroadcastChannel: Clone {
   type Resource: Resource;
 
-  fn subscribe(&self) -> Result<Self::Resource, AnyError>;
+  fn subscribe(&self) -> Result<Self::Resource, BroadcastChannelError>;
 
-  fn unsubscribe(&self, resource: &Self::Resource) -> Result<(), AnyError>;
+  fn unsubscribe(
+    &self,
+    resource: &Self::Resource,
+  ) -> Result<(), BroadcastChannelError>;
 
   async fn send(
     &self,
     resource: &Self::Resource,
     name: String,
     data: Vec<u8>,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), BroadcastChannelError>;
 
   async fn recv(
     &self,
     resource: &Self::Resource,
-  ) -> Result<Option<Message>, AnyError>;
+  ) -> Result<Option<Message>, BroadcastChannelError>;
 }
 
 pub type Message = (String, Vec<u8>);
@@ -46,7 +81,7 @@ pub type Message = (String, Vec<u8>);
 #[smi]
 pub fn op_broadcast_subscribe<BC>(
   state: &mut OpState,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, BroadcastChannelError>
 where
   BC: BroadcastChannel + 'static,
 {
@@ -62,11 +97,14 @@ where
 pub fn op_broadcast_unsubscribe<BC>(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError>
+) -> Result<(), BroadcastChannelError>
 where
   BC: BroadcastChannel + 'static,
 {
-  let resource = state.resource_table.get::<BC::Resource>(rid)?;
+  let resource = state
+    .resource_table
+    .get::<BC::Resource>(rid)
+    .map_err(BroadcastChannelError::Resource)?;
   let bc = state.borrow::<BC>();
   bc.unsubscribe(&resource)
 }
@@ -77,11 +115,15 @@ pub async fn op_broadcast_send<BC>(
   #[smi] rid: ResourceId,
   #[string] name: String,
   #[buffer] buf: JsBuffer,
-) -> Result<(), AnyError>
+) -> Result<(), BroadcastChannelError>
 where
   BC: BroadcastChannel + 'static,
 {
-  let resource = state.borrow().resource_table.get::<BC::Resource>(rid)?;
+  let resource = state
+    .borrow()
+    .resource_table
+    .get::<BC::Resource>(rid)
+    .map_err(BroadcastChannelError::Resource)?;
   let bc = state.borrow().borrow::<BC>().clone();
   bc.send(&resource, name, buf.to_vec()).await
 }
@@ -91,11 +133,15 @@ where
 pub async fn op_broadcast_recv<BC>(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<Message>, AnyError>
+) -> Result<Option<Message>, BroadcastChannelError>
 where
   BC: BroadcastChannel + 'static,
 {
-  let resource = state.borrow().resource_table.get::<BC::Resource>(rid)?;
+  let resource = state
+    .borrow()
+    .resource_table
+    .get::<BC::Resource>(rid)
+    .map_err(BroadcastChannelError::Resource)?;
   let bc = state.borrow().borrow::<BC>().clone();
   bc.recv(&resource).await
 }
diff --git a/ext/cache/Cargo.toml b/ext/cache/Cargo.toml
index 71ca34380c..7cae8d88a2 100644
--- a/ext/cache/Cargo.toml
+++ b/ext/cache/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_cache"
-version = "0.103.0"
+version = "0.107.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -19,4 +19,5 @@ deno_core.workspace = true
 rusqlite.workspace = true
 serde.workspace = true
 sha2.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
diff --git a/ext/cache/lib.rs b/ext/cache/lib.rs
index f6d758b95c..b9cc5427c2 100644
--- a/ext/cache/lib.rs
+++ b/ext/cache/lib.rs
@@ -7,7 +7,6 @@ use std::sync::Arc;
 
 use async_trait::async_trait;
 use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde::Deserialize;
 use deno_core::serde::Serialize;
@@ -19,6 +18,20 @@ use deno_core::ResourceId;
 mod sqlite;
 pub use sqlite::SqliteBackedCache;
 
+#[derive(Debug, thiserror::Error)]
+pub enum CacheError {
+  #[error(transparent)]
+  Sqlite(#[from] rusqlite::Error),
+  #[error(transparent)]
+  JoinError(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+}
+
 #[derive(Clone)]
 pub struct CreateCache<C: Cache + 'static>(pub Arc<dyn Fn() -> C>);
 
@@ -92,26 +105,31 @@ pub struct CacheDeleteRequest {
 pub trait Cache: Clone + 'static {
   type CacheMatchResourceType: Resource;
 
-  async fn storage_open(&self, cache_name: String) -> Result<i64, AnyError>;
-  async fn storage_has(&self, cache_name: String) -> Result<bool, AnyError>;
-  async fn storage_delete(&self, cache_name: String) -> Result<bool, AnyError>;
+  async fn storage_open(&self, cache_name: String) -> Result<i64, CacheError>;
+  async fn storage_has(&self, cache_name: String) -> Result<bool, CacheError>;
+  async fn storage_delete(
+    &self,
+    cache_name: String,
+  ) -> Result<bool, CacheError>;
 
   /// Put a resource into the cache.
   async fn put(
     &self,
     request_response: CachePutRequest,
     resource: Option<Rc<dyn Resource>>,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), CacheError>;
 
   async fn r#match(
     &self,
     request: CacheMatchRequest,
   ) -> Result<
     Option<(CacheMatchResponseMeta, Option<Self::CacheMatchResourceType>)>,
-    AnyError,
+    CacheError,
   >;
-  async fn delete(&self, request: CacheDeleteRequest)
-    -> Result<bool, AnyError>;
+  async fn delete(
+    &self,
+    request: CacheDeleteRequest,
+  ) -> Result<bool, CacheError>;
 }
 
 #[op2(async)]
@@ -119,7 +137,7 @@ pub trait Cache: Clone + 'static {
 pub async fn op_cache_storage_open<CA>(
   state: Rc<RefCell<OpState>>,
   #[string] cache_name: String,
-) -> Result<i64, AnyError>
+) -> Result<i64, CacheError>
 where
   CA: Cache,
 {
@@ -131,7 +149,7 @@ where
 pub async fn op_cache_storage_has<CA>(
   state: Rc<RefCell<OpState>>,
   #[string] cache_name: String,
-) -> Result<bool, AnyError>
+) -> Result<bool, CacheError>
 where
   CA: Cache,
 {
@@ -143,7 +161,7 @@ where
 pub async fn op_cache_storage_delete<CA>(
   state: Rc<RefCell<OpState>>,
   #[string] cache_name: String,
-) -> Result<bool, AnyError>
+) -> Result<bool, CacheError>
 where
   CA: Cache,
 {
@@ -155,13 +173,19 @@ where
 pub async fn op_cache_put<CA>(
   state: Rc<RefCell<OpState>>,
   #[serde] request_response: CachePutRequest,
-) -> Result<(), AnyError>
+) -> Result<(), CacheError>
 where
   CA: Cache,
 {
   let cache = get_cache::<CA>(&state)?;
   let resource = match request_response.response_rid {
-    Some(rid) => Some(state.borrow_mut().resource_table.take_any(rid)?),
+    Some(rid) => Some(
+      state
+        .borrow_mut()
+        .resource_table
+        .take_any(rid)
+        .map_err(CacheError::Resource)?,
+    ),
     None => None,
   };
   cache.put(request_response, resource).await
@@ -172,7 +196,7 @@ where
 pub async fn op_cache_match<CA>(
   state: Rc<RefCell<OpState>>,
   #[serde] request: CacheMatchRequest,
-) -> Result<Option<CacheMatchResponse>, AnyError>
+) -> Result<Option<CacheMatchResponse>, CacheError>
 where
   CA: Cache,
 {
@@ -191,7 +215,7 @@ where
 pub async fn op_cache_delete<CA>(
   state: Rc<RefCell<OpState>>,
   #[serde] request: CacheDeleteRequest,
-) -> Result<bool, AnyError>
+) -> Result<bool, CacheError>
 where
   CA: Cache,
 {
@@ -199,7 +223,7 @@ where
   cache.delete(request).await
 }
 
-pub fn get_cache<CA>(state: &Rc<RefCell<OpState>>) -> Result<CA, AnyError>
+pub fn get_cache<CA>(state: &Rc<RefCell<OpState>>) -> Result<CA, CacheError>
 where
   CA: Cache,
 {
@@ -211,7 +235,9 @@ where
     state.put(cache);
     Ok(state.borrow::<CA>().clone())
   } else {
-    Err(type_error("CacheStorage is not available in this context"))
+    Err(CacheError::Other(type_error(
+      "CacheStorage is not available in this context",
+    )))
   }
 }
 
diff --git a/ext/cache/sqlite.rs b/ext/cache/sqlite.rs
index c3c55dd5e9..e4991c32f1 100644
--- a/ext/cache/sqlite.rs
+++ b/ext/cache/sqlite.rs
@@ -30,6 +30,7 @@ use crate::serialize_headers;
 use crate::vary_header_matches;
 use crate::Cache;
 use crate::CacheDeleteRequest;
+use crate::CacheError;
 use crate::CacheMatchRequest;
 use crate::CacheMatchResponseMeta;
 use crate::CachePutRequest;
@@ -102,7 +103,7 @@ impl Cache for SqliteBackedCache {
   /// Open a cache storage. Internally, this creates a row in the
   /// sqlite db if the cache doesn't exist and returns the internal id
   /// of the cache.
-  async fn storage_open(&self, cache_name: String) -> Result<i64, AnyError> {
+  async fn storage_open(&self, cache_name: String) -> Result<i64, CacheError> {
     let db = self.connection.clone();
     let cache_storage_dir = self.cache_storage_dir.clone();
     spawn_blocking(move || {
@@ -121,14 +122,14 @@ impl Cache for SqliteBackedCache {
       )?;
       let responses_dir = get_responses_dir(cache_storage_dir, cache_id);
       std::fs::create_dir_all(responses_dir)?;
-      Ok::<i64, AnyError>(cache_id)
+      Ok::<i64, CacheError>(cache_id)
     })
     .await?
   }
 
   /// Check if a cache with the provided name exists.
   /// Note: this doesn't check the disk, it only checks the sqlite db.
-  async fn storage_has(&self, cache_name: String) -> Result<bool, AnyError> {
+  async fn storage_has(&self, cache_name: String) -> Result<bool, CacheError> {
     let db = self.connection.clone();
     spawn_blocking(move || {
       let db = db.lock();
@@ -140,13 +141,16 @@ impl Cache for SqliteBackedCache {
           Ok(count > 0)
         },
       )?;
-      Ok::<bool, AnyError>(cache_exists)
+      Ok::<bool, CacheError>(cache_exists)
     })
     .await?
   }
 
   /// Delete a cache storage. Internally, this deletes the row in the sqlite db.
-  async fn storage_delete(&self, cache_name: String) -> Result<bool, AnyError> {
+  async fn storage_delete(
+    &self,
+    cache_name: String,
+  ) -> Result<bool, CacheError> {
     let db = self.connection.clone();
     let cache_storage_dir = self.cache_storage_dir.clone();
     spawn_blocking(move || {
@@ -167,7 +171,7 @@ impl Cache for SqliteBackedCache {
           std::fs::remove_dir_all(cache_dir)?;
         }
       }
-      Ok::<bool, AnyError>(maybe_cache_id.is_some())
+      Ok::<bool, CacheError>(maybe_cache_id.is_some())
     })
     .await?
   }
@@ -176,10 +180,12 @@ impl Cache for SqliteBackedCache {
     &self,
     request_response: CachePutRequest,
     resource: Option<Rc<dyn Resource>>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), CacheError> {
     let db = self.connection.clone();
     let cache_storage_dir = self.cache_storage_dir.clone();
-    let now = SystemTime::now().duration_since(UNIX_EPOCH)?;
+    let now = SystemTime::now()
+      .duration_since(UNIX_EPOCH)
+      .expect("SystemTime is before unix epoch");
 
     if let Some(resource) = resource {
       let body_key = hash(&format!(
@@ -193,7 +199,11 @@ impl Cache for SqliteBackedCache {
       let mut file = tokio::fs::File::create(response_path).await?;
       let mut buf = BufMutView::new(64 * 1024);
       loop {
-        let (size, buf2) = resource.clone().read_byob(buf).await?;
+        let (size, buf2) = resource
+          .clone()
+          .read_byob(buf)
+          .await
+          .map_err(CacheError::Other)?;
         if size == 0 {
           break;
         }
@@ -224,7 +234,7 @@ impl Cache for SqliteBackedCache {
     request: CacheMatchRequest,
   ) -> Result<
     Option<(CacheMatchResponseMeta, Option<CacheResponseResource>)>,
-    AnyError,
+    CacheError,
   > {
     let db = self.connection.clone();
     let cache_storage_dir = self.cache_storage_dir.clone();
@@ -290,19 +300,17 @@ impl Cache for SqliteBackedCache {
           }
           Err(err) => return Err(err.into()),
         };
-        return Ok(Some((cache_meta, Some(CacheResponseResource::new(file)))));
+        Ok(Some((cache_meta, Some(CacheResponseResource::new(file)))))
       }
-      Some((cache_meta, None)) => {
-        return Ok(Some((cache_meta, None)));
-      }
-      None => return Ok(None),
+      Some((cache_meta, None)) => Ok(Some((cache_meta, None))),
+      None => Ok(None),
     }
   }
 
   async fn delete(
     &self,
     request: CacheDeleteRequest,
-  ) -> Result<bool, AnyError> {
+  ) -> Result<bool, CacheError> {
     let db = self.connection.clone();
     spawn_blocking(move || {
       // TODO(@satyarohith): remove the response body from disk if one exists
@@ -311,17 +319,17 @@ impl Cache for SqliteBackedCache {
         "DELETE FROM request_response_list WHERE cache_id = ?1 AND request_url = ?2",
         (request.cache_id, &request.request_url),
       )?;
-      Ok::<bool, AnyError>(rows_effected > 0)
+      Ok::<bool, CacheError>(rows_effected > 0)
     })
     .await?
   }
 }
 
 async fn insert_cache_asset(
-  db: Arc<Mutex<rusqlite::Connection>>,
+  db: Arc<Mutex<Connection>>,
   put: CachePutRequest,
   response_body_key: Option<String>,
-) -> Result<Option<String>, deno_core::anyhow::Error> {
+) -> Result<Option<String>, CacheError> {
   spawn_blocking(move || {
     let maybe_response_body = {
       let db = db.lock();
@@ -339,7 +347,7 @@ async fn insert_cache_asset(
           response_body_key,
           put.response_status,
           put.response_status_text,
-          SystemTime::now().duration_since(UNIX_EPOCH)?.as_secs(),
+          SystemTime::now().duration_since(UNIX_EPOCH).expect("SystemTime is before unix epoch").as_secs(),
         ),
         |row| {
           let response_body_key: Option<String> = row.get(0)?;
@@ -347,7 +355,7 @@ async fn insert_cache_asset(
         },
       )?
     };
-      Ok::<Option<String>, AnyError>(maybe_response_body)
+    Ok::<Option<String>, CacheError>(maybe_response_body)
   }).await?
 }
 
diff --git a/ext/canvas/Cargo.toml b/ext/canvas/Cargo.toml
index 47c37560ec..5d2c371999 100644
--- a/ext/canvas/Cargo.toml
+++ b/ext/canvas/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_canvas"
-version = "0.40.0"
+version = "0.44.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -18,3 +18,4 @@ deno_core.workspace = true
 deno_webgpu.workspace = true
 image = { version = "0.24.7", default-features = false, features = ["png"] }
 serde = { workspace = true, features = ["derive"] }
+thiserror.workspace = true
diff --git a/ext/canvas/lib.rs b/ext/canvas/lib.rs
index 72173f1331..defb288ac9 100644
--- a/ext/canvas/lib.rs
+++ b/ext/canvas/lib.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 use image::imageops::FilterType;
@@ -13,6 +11,14 @@ use serde::Deserialize;
 use serde::Serialize;
 use std::path::PathBuf;
 
+#[derive(Debug, thiserror::Error)]
+pub enum CanvasError {
+  #[error("Color type '{0:?}' not supported")]
+  UnsupportedColorType(ColorType),
+  #[error(transparent)]
+  Image(#[from] image::ImageError),
+}
+
 #[derive(Debug, Deserialize)]
 #[serde(rename_all = "snake_case")]
 enum ImageResizeQuality {
@@ -43,7 +49,7 @@ struct ImageProcessArgs {
 fn op_image_process(
   #[buffer] buf: &[u8],
   #[serde] args: ImageProcessArgs,
-) -> Result<ToJsBuffer, AnyError> {
+) -> ToJsBuffer {
   let view =
     RgbaImage::from_vec(args.width, args.height, buf.to_vec()).unwrap();
 
@@ -105,7 +111,7 @@ fn op_image_process(
     }
   }
 
-  Ok(image_out.to_vec().into())
+  image_out.to_vec().into()
 }
 
 #[derive(Debug, Serialize)]
@@ -117,17 +123,16 @@ struct DecodedPng {
 
 #[op2]
 #[serde]
-fn op_image_decode_png(#[buffer] buf: &[u8]) -> Result<DecodedPng, AnyError> {
+fn op_image_decode_png(
+  #[buffer] buf: &[u8],
+) -> Result<DecodedPng, CanvasError> {
   let png = image::codecs::png::PngDecoder::new(buf)?;
 
   let (width, height) = png.dimensions();
 
   // TODO(@crowlKats): maybe use DynamicImage https://docs.rs/image/0.24.7/image/enum.DynamicImage.html ?
   if png.color_type() != ColorType::Rgba8 {
-    return Err(type_error(format!(
-      "Color type '{:?}' not supported",
-      png.color_type()
-    )));
+    return Err(CanvasError::UnsupportedColorType(png.color_type()));
   }
 
   // read_image will assert that the buffer is the correct size, so we need to fill it with zeros
diff --git a/ext/console/01_console.js b/ext/console/01_console.js
index d9acc958a0..3803492b90 100644
--- a/ext/console/01_console.js
+++ b/ext/console/01_console.js
@@ -84,6 +84,7 @@ const {
   NumberIsInteger,
   NumberIsNaN,
   NumberParseInt,
+  NumberParseFloat,
   NumberPrototypeToFixed,
   NumberPrototypeToString,
   NumberPrototypeValueOf,
@@ -2652,6 +2653,7 @@ const HSL_PATTERN = new SafeRegExp(
 );
 
 function parseCssColor(colorString) {
+  colorString = StringPrototypeToLowerCase(colorString);
   if (colorKeywords.has(colorString)) {
     colorString = colorKeywords.get(colorString);
   }
@@ -3010,20 +3012,18 @@ function inspectArgs(args, inspectOptions = { __proto__: null }) {
           } else if (ArrayPrototypeIncludes(["d", "i"], char)) {
             // Format as an integer.
             const value = args[a++];
-            if (typeof value == "bigint") {
-              formattedArg = `${value}n`;
-            } else if (typeof value == "number") {
-              formattedArg = `${NumberParseInt(String(value))}`;
-            } else {
+            if (typeof value === "symbol") {
               formattedArg = "NaN";
+            } else {
+              formattedArg = `${NumberParseInt(value)}`;
             }
           } else if (char == "f") {
             // Format as a floating point value.
             const value = args[a++];
-            if (typeof value == "number") {
-              formattedArg = `${value}`;
-            } else {
+            if (typeof value === "symbol") {
               formattedArg = "NaN";
+            } else {
+              formattedArg = `${NumberParseFloat(value)}`;
             }
           } else if (ArrayPrototypeIncludes(["O", "o"], char)) {
             // Format as an object.
@@ -3257,7 +3257,7 @@ class Console {
 
     const stringifyValue = (value) =>
       inspectValueWithQuotes(value, {
-        ...getDefaultInspectOptions(),
+        ...getConsoleInspectOptions(noColorStdout()),
         depth: 1,
         compact: true,
       });
diff --git a/ext/console/Cargo.toml b/ext/console/Cargo.toml
index 5c143ca18c..b3543ed85f 100644
--- a/ext/console/Cargo.toml
+++ b/ext/console/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_console"
-version = "0.171.0"
+version = "0.175.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/cron/Cargo.toml b/ext/cron/Cargo.toml
index a773521f5b..0d52cb6a97 100644
--- a/ext/cron/Cargo.toml
+++ b/ext/cron/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_cron"
-version = "0.51.0"
+version = "0.55.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -19,4 +19,5 @@ async-trait.workspace = true
 chrono = { workspace = true, features = ["now"] }
 deno_core.workspace = true
 saffron.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
diff --git a/ext/cron/interface.rs b/ext/cron/interface.rs
index 01b1d17895..a19525cc4e 100644
--- a/ext/cron/interface.rs
+++ b/ext/cron/interface.rs
@@ -1,17 +1,17 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use crate::CronError;
 use async_trait::async_trait;
-use deno_core::error::AnyError;
 
 pub trait CronHandler {
   type EH: CronHandle + 'static;
 
-  fn create(&self, spec: CronSpec) -> Result<Self::EH, AnyError>;
+  fn create(&self, spec: CronSpec) -> Result<Self::EH, CronError>;
 }
 
 #[async_trait(?Send)]
 pub trait CronHandle {
-  async fn next(&self, prev_success: bool) -> Result<bool, AnyError>;
+  async fn next(&self, prev_success: bool) -> Result<bool, CronError>;
   fn close(&self);
 }
 
diff --git a/ext/cron/lib.rs b/ext/cron/lib.rs
index e350e4d698..feffb5e511 100644
--- a/ext/cron/lib.rs
+++ b/ext/cron/lib.rs
@@ -7,16 +7,13 @@ use std::borrow::Cow;
 use std::cell::RefCell;
 use std::rc::Rc;
 
+pub use crate::interface::*;
 use deno_core::error::get_custom_error_class;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
 use deno_core::ResourceId;
 
-pub use crate::interface::*;
-
 pub const UNSTABLE_FEATURE_NAME: &str = "cron";
 
 deno_core::extension!(deno_cron,
@@ -49,6 +46,28 @@ impl<EH: CronHandle + 'static> Resource for CronResource<EH> {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum CronError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("Cron name cannot exceed 64 characters: current length {0}")]
+  NameExceeded(usize),
+  #[error("Invalid cron name: only alphanumeric characters, whitespace, hyphens, and underscores are allowed")]
+  NameInvalid,
+  #[error("Cron with this name already exists")]
+  AlreadyExists,
+  #[error("Too many crons")]
+  TooManyCrons,
+  #[error("Invalid cron schedule")]
+  InvalidCron,
+  #[error("Invalid backoff schedule")]
+  InvalidBackoff,
+  #[error(transparent)]
+  AcquireError(#[from] tokio::sync::AcquireError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[op2]
 #[smi]
 fn op_cron_create<C>(
@@ -56,7 +75,7 @@ fn op_cron_create<C>(
   #[string] name: String,
   #[string] cron_schedule: String,
   #[serde] backoff_schedule: Option<Vec<u32>>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, CronError>
 where
   C: CronHandler + 'static,
 {
@@ -90,7 +109,7 @@ async fn op_cron_next<C>(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   prev_success: bool,
-) -> Result<bool, AnyError>
+) -> Result<bool, CronError>
 where
   C: CronHandler + 'static,
 {
@@ -102,7 +121,7 @@ where
         if get_custom_error_class(&err) == Some("BadResource") {
           return Ok(false);
         } else {
-          return Err(err);
+          return Err(CronError::Resource(err));
         }
       }
     };
@@ -112,17 +131,14 @@ where
   cron_handler.next(prev_success).await
 }
 
-fn validate_cron_name(name: &str) -> Result<(), AnyError> {
+fn validate_cron_name(name: &str) -> Result<(), CronError> {
   if name.len() > 64 {
-    return Err(type_error(format!(
-      "Cron name cannot exceed 64 characters: current length {}",
-      name.len()
-    )));
+    return Err(CronError::NameExceeded(name.len()));
   }
   if !name.chars().all(|c| {
     c.is_ascii_whitespace() || c.is_ascii_alphanumeric() || c == '_' || c == '-'
   }) {
-    return Err(type_error("Invalid cron name: only alphanumeric characters, whitespace, hyphens, and underscores are allowed"));
+    return Err(CronError::NameInvalid);
   }
   Ok(())
 }
diff --git a/ext/cron/local.rs b/ext/cron/local.rs
index dd60e750a0..1110baadb8 100644
--- a/ext/cron/local.rs
+++ b/ext/cron/local.rs
@@ -10,8 +10,6 @@ use std::rc::Weak;
 use std::sync::Arc;
 
 use async_trait::async_trait;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures;
 use deno_core::futures::FutureExt;
 use deno_core::unsync::spawn;
@@ -21,6 +19,7 @@ use tokio::sync::mpsc::WeakSender;
 use tokio::sync::OwnedSemaphorePermit;
 use tokio::sync::Semaphore;
 
+use crate::CronError;
 use crate::CronHandle;
 use crate::CronHandler;
 use crate::CronSpec;
@@ -81,7 +80,7 @@ impl LocalCronHandler {
   async fn cron_loop(
     runtime_state: Rc<RefCell<RuntimeState>>,
     mut cron_schedule_rx: mpsc::Receiver<(String, bool)>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), CronError> {
     loop {
       let earliest_deadline = runtime_state
         .borrow()
@@ -154,7 +153,7 @@ impl LocalCronHandler {
 impl RuntimeState {
   fn get_ready_crons(
     &mut self,
-  ) -> Result<Vec<(String, WeakSender<()>)>, AnyError> {
+  ) -> Result<Vec<(String, WeakSender<()>)>, CronError> {
     let now = chrono::Utc::now().timestamp_millis() as u64;
 
     let ready = {
@@ -191,7 +190,7 @@ impl RuntimeState {
 impl CronHandler for LocalCronHandler {
   type EH = CronExecutionHandle;
 
-  fn create(&self, spec: CronSpec) -> Result<Self::EH, AnyError> {
+  fn create(&self, spec: CronSpec) -> Result<Self::EH, CronError> {
     // Ensure that the cron loop is started.
     self.cron_loop_join_handle.get_or_init(|| {
       let (cron_schedule_tx, cron_schedule_rx) =
@@ -208,17 +207,17 @@ impl CronHandler for LocalCronHandler {
     let mut runtime_state = self.runtime_state.borrow_mut();
 
     if runtime_state.crons.len() > MAX_CRONS {
-      return Err(type_error("Too many crons"));
+      return Err(CronError::TooManyCrons);
     }
     if runtime_state.crons.contains_key(&spec.name) {
-      return Err(type_error("Cron with this name already exists"));
+      return Err(CronError::AlreadyExists);
     }
 
     // Validate schedule expression.
     spec
       .cron_schedule
       .parse::<saffron::Cron>()
-      .map_err(|_| type_error("Invalid cron schedule"))?;
+      .map_err(|_| CronError::InvalidCron)?;
 
     // Validate backoff_schedule.
     if let Some(backoff_schedule) = &spec.backoff_schedule {
@@ -263,7 +262,7 @@ struct Inner {
 
 #[async_trait(?Send)]
 impl CronHandle for CronExecutionHandle {
-  async fn next(&self, prev_success: bool) -> Result<bool, AnyError> {
+  async fn next(&self, prev_success: bool) -> Result<bool, CronError> {
     self.inner.borrow_mut().permit.take();
 
     if self
@@ -300,7 +299,7 @@ impl CronHandle for CronExecutionHandle {
   }
 }
 
-fn compute_next_deadline(cron_expression: &str) -> Result<u64, AnyError> {
+fn compute_next_deadline(cron_expression: &str) -> Result<u64, CronError> {
   let now = chrono::Utc::now();
 
   if let Ok(test_schedule) = env::var("DENO_CRON_TEST_SCHEDULE_OFFSET") {
@@ -311,19 +310,21 @@ fn compute_next_deadline(cron_expression: &str) -> Result<u64, AnyError> {
 
   let cron = cron_expression
     .parse::<saffron::Cron>()
-    .map_err(|_| anyhow::anyhow!("invalid cron expression"))?;
+    .map_err(|_| CronError::InvalidCron)?;
   let Some(next_deadline) = cron.next_after(now) else {
-    return Err(anyhow::anyhow!("invalid cron expression"));
+    return Err(CronError::InvalidCron);
   };
   Ok(next_deadline.timestamp_millis() as u64)
 }
 
-fn validate_backoff_schedule(backoff_schedule: &[u32]) -> Result<(), AnyError> {
+fn validate_backoff_schedule(
+  backoff_schedule: &[u32],
+) -> Result<(), CronError> {
   if backoff_schedule.len() > MAX_BACKOFF_COUNT {
-    return Err(type_error("Invalid backoff schedule"));
+    return Err(CronError::InvalidBackoff);
   }
   if backoff_schedule.iter().any(|s| *s > MAX_BACKOFF_MS) {
-    return Err(type_error("Invalid backoff schedule"));
+    return Err(CronError::InvalidBackoff);
   }
   Ok(())
 }
diff --git a/ext/crypto/Cargo.toml b/ext/crypto/Cargo.toml
index c81c8f6a70..95981bba3b 100644
--- a/ext/crypto/Cargo.toml
+++ b/ext/crypto/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_crypto"
-version = "0.185.0"
+version = "0.189.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -41,5 +41,7 @@ sha1.workspace = true
 sha2.workspace = true
 signature.workspace = true
 spki.workspace = true
+thiserror.workspace = true
+tokio.workspace = true
 uuid.workspace = true
 x25519-dalek = "2.0.0"
diff --git a/ext/crypto/decrypt.rs b/ext/crypto/decrypt.rs
index 9b104e1784..1140475183 100644
--- a/ext/crypto/decrypt.rs
+++ b/ext/crypto/decrypt.rs
@@ -16,9 +16,6 @@ use ctr::cipher::StreamCipher;
 use ctr::Ctr128BE;
 use ctr::Ctr32BE;
 use ctr::Ctr64BE;
-use deno_core::error::custom_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::unsync::spawn_blocking;
 use deno_core::JsBuffer;
@@ -73,12 +70,36 @@ pub enum DecryptAlgorithm {
   },
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum DecryptError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error(transparent)]
+  Pkcs1(#[from] rsa::pkcs1::Error),
+  #[error("Decryption failed")]
+  Failed,
+  #[error("invalid length")]
+  InvalidLength,
+  #[error("invalid counter length. Currently supported 32/64/128 bits")]
+  InvalidCounterLength,
+  #[error("tag length not equal to 128")]
+  InvalidTagLength,
+  #[error("invalid key or iv")]
+  InvalidKeyOrIv,
+  #[error("tried to decrypt too much data")]
+  TooMuchData,
+  #[error("iv length not equal to 12 or 16")]
+  InvalidIvLength,
+  #[error("{0}")]
+  Rsa(rsa::Error),
+}
+
 #[op2(async)]
 #[serde]
 pub async fn op_crypto_decrypt(
   #[serde] opts: DecryptOptions,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, DecryptError> {
   let key = opts.key;
   let fun = move || match opts.algorithm {
     DecryptAlgorithm::RsaOaep { hash, label } => {
@@ -108,7 +129,7 @@ fn decrypt_rsa_oaep(
   hash: ShaHash,
   label: Vec<u8>,
   data: &[u8],
-) -> Result<Vec<u8>, deno_core::anyhow::Error> {
+) -> Result<Vec<u8>, DecryptError> {
   let key = key.as_rsa_private_key()?;
 
   let private_key = rsa::RsaPrivateKey::from_pkcs1_der(key)?;
@@ -139,7 +160,7 @@ fn decrypt_rsa_oaep(
 
   private_key
     .decrypt(padding, data)
-    .map_err(|e| custom_error("DOMExceptionOperationError", e.to_string()))
+    .map_err(DecryptError::Rsa)
 }
 
 fn decrypt_aes_cbc(
@@ -147,7 +168,7 @@ fn decrypt_aes_cbc(
   length: usize,
   iv: Vec<u8>,
   data: &[u8],
-) -> Result<Vec<u8>, deno_core::anyhow::Error> {
+) -> Result<Vec<u8>, DecryptError> {
   let key = key.as_secret_key()?;
 
   // 2.
@@ -155,53 +176,32 @@ fn decrypt_aes_cbc(
     128 => {
       // Section 10.3 Step 2 of RFC 2315 https://www.rfc-editor.org/rfc/rfc2315
       type Aes128CbcDec = cbc::Decryptor<aes::Aes128>;
-      let cipher = Aes128CbcDec::new_from_slices(key, &iv).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Invalid key or iv".to_string(),
-        )
-      })?;
+      let cipher = Aes128CbcDec::new_from_slices(key, &iv)
+        .map_err(|_| DecryptError::InvalidKeyOrIv)?;
 
-      cipher.decrypt_padded_vec_mut::<Pkcs7>(data).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Decryption failed".to_string(),
-        )
-      })?
+      cipher
+        .decrypt_padded_vec_mut::<Pkcs7>(data)
+        .map_err(|_| DecryptError::Failed)?
     }
     192 => {
       // Section 10.3 Step 2 of RFC 2315 https://www.rfc-editor.org/rfc/rfc2315
       type Aes192CbcDec = cbc::Decryptor<aes::Aes192>;
-      let cipher = Aes192CbcDec::new_from_slices(key, &iv).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Invalid key or iv".to_string(),
-        )
-      })?;
+      let cipher = Aes192CbcDec::new_from_slices(key, &iv)
+        .map_err(|_| DecryptError::InvalidKeyOrIv)?;
 
-      cipher.decrypt_padded_vec_mut::<Pkcs7>(data).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Decryption failed".to_string(),
-        )
-      })?
+      cipher
+        .decrypt_padded_vec_mut::<Pkcs7>(data)
+        .map_err(|_| DecryptError::Failed)?
     }
     256 => {
       // Section 10.3 Step 2 of RFC 2315 https://www.rfc-editor.org/rfc/rfc2315
       type Aes256CbcDec = cbc::Decryptor<aes::Aes256>;
-      let cipher = Aes256CbcDec::new_from_slices(key, &iv).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Invalid key or iv".to_string(),
-        )
-      })?;
+      let cipher = Aes256CbcDec::new_from_slices(key, &iv)
+        .map_err(|_| DecryptError::InvalidKeyOrIv)?;
 
-      cipher.decrypt_padded_vec_mut::<Pkcs7>(data).map_err(|_| {
-        custom_error(
-          "DOMExceptionOperationError",
-          "Decryption failed".to_string(),
-        )
-      })?
+      cipher
+        .decrypt_padded_vec_mut::<Pkcs7>(data)
+        .map_err(|_| DecryptError::Failed)?
     }
     _ => unreachable!(),
   };
@@ -214,7 +214,7 @@ fn decrypt_aes_ctr_gen<B>(
   key: &[u8],
   counter: &[u8],
   data: &[u8],
-) -> Result<Vec<u8>, AnyError>
+) -> Result<Vec<u8>, DecryptError>
 where
   B: KeyIvInit + StreamCipher,
 {
@@ -223,7 +223,7 @@ where
   let mut plaintext = data.to_vec();
   cipher
     .try_apply_keystream(&mut plaintext)
-    .map_err(|_| operation_error("tried to decrypt too much data"))?;
+    .map_err(|_| DecryptError::TooMuchData)?;
 
   Ok(plaintext)
 }
@@ -235,12 +235,12 @@ fn decrypt_aes_gcm_gen<N: ArrayLength<u8>>(
   length: usize,
   additional_data: Vec<u8>,
   plaintext: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), DecryptError> {
   let nonce = Nonce::from_slice(nonce);
   match length {
     128 => {
       let cipher = aes_gcm::AesGcm::<Aes128, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Decryption failed"))?;
+        .map_err(|_| DecryptError::Failed)?;
       cipher
         .decrypt_in_place_detached(
           nonce,
@@ -248,11 +248,11 @@ fn decrypt_aes_gcm_gen<N: ArrayLength<u8>>(
           plaintext,
           tag,
         )
-        .map_err(|_| operation_error("Decryption failed"))?
+        .map_err(|_| DecryptError::Failed)?
     }
     192 => {
       let cipher = aes_gcm::AesGcm::<Aes192, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Decryption failed"))?;
+        .map_err(|_| DecryptError::Failed)?;
       cipher
         .decrypt_in_place_detached(
           nonce,
@@ -260,11 +260,11 @@ fn decrypt_aes_gcm_gen<N: ArrayLength<u8>>(
           plaintext,
           tag,
         )
-        .map_err(|_| operation_error("Decryption failed"))?
+        .map_err(|_| DecryptError::Failed)?
     }
     256 => {
       let cipher = aes_gcm::AesGcm::<Aes256, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Decryption failed"))?;
+        .map_err(|_| DecryptError::Failed)?;
       cipher
         .decrypt_in_place_detached(
           nonce,
@@ -272,9 +272,9 @@ fn decrypt_aes_gcm_gen<N: ArrayLength<u8>>(
           plaintext,
           tag,
         )
-        .map_err(|_| operation_error("Decryption failed"))?
+        .map_err(|_| DecryptError::Failed)?
     }
-    _ => return Err(type_error("invalid length")),
+    _ => return Err(DecryptError::InvalidLength),
   };
 
   Ok(())
@@ -286,7 +286,7 @@ fn decrypt_aes_ctr(
   counter: &[u8],
   ctr_length: usize,
   data: &[u8],
-) -> Result<Vec<u8>, deno_core::anyhow::Error> {
+) -> Result<Vec<u8>, DecryptError> {
   let key = key.as_secret_key()?;
 
   match ctr_length {
@@ -294,23 +294,21 @@ fn decrypt_aes_ctr(
       128 => decrypt_aes_ctr_gen::<Ctr32BE<aes::Aes128>>(key, counter, data),
       192 => decrypt_aes_ctr_gen::<Ctr32BE<aes::Aes192>>(key, counter, data),
       256 => decrypt_aes_ctr_gen::<Ctr32BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(DecryptError::InvalidLength),
     },
     64 => match key_length {
       128 => decrypt_aes_ctr_gen::<Ctr64BE<aes::Aes128>>(key, counter, data),
       192 => decrypt_aes_ctr_gen::<Ctr64BE<aes::Aes192>>(key, counter, data),
       256 => decrypt_aes_ctr_gen::<Ctr64BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(DecryptError::InvalidLength),
     },
     128 => match key_length {
       128 => decrypt_aes_ctr_gen::<Ctr128BE<aes::Aes128>>(key, counter, data),
       192 => decrypt_aes_ctr_gen::<Ctr128BE<aes::Aes192>>(key, counter, data),
       256 => decrypt_aes_ctr_gen::<Ctr128BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(DecryptError::InvalidLength),
     },
-    _ => Err(type_error(
-      "invalid counter length. Currently supported 32/64/128 bits",
-    )),
+    _ => Err(DecryptError::InvalidCounterLength),
   }
 }
 
@@ -321,7 +319,7 @@ fn decrypt_aes_gcm(
   iv: Vec<u8>,
   additional_data: Option<Vec<u8>>,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, DecryptError> {
   let key = key.as_secret_key()?;
   let additional_data = additional_data.unwrap_or_default();
 
@@ -330,7 +328,7 @@ fn decrypt_aes_gcm(
   // Note that encryption won't fail, it instead truncates the tag
   // to the specified tag length as specified in the spec.
   if tag_length != 128 {
-    return Err(type_error("tag length not equal to 128"));
+    return Err(DecryptError::InvalidTagLength);
   }
 
   let sep = data.len() - (tag_length / 8);
@@ -357,7 +355,7 @@ fn decrypt_aes_gcm(
       additional_data,
       &mut plaintext,
     )?,
-    _ => return Err(type_error("iv length not equal to 12 or 16")),
+    _ => return Err(DecryptError::InvalidIvLength),
   }
 
   Ok(plaintext)
diff --git a/ext/crypto/ed25519.rs b/ext/crypto/ed25519.rs
index 4f604fe513..da34b7d25d 100644
--- a/ext/crypto/ed25519.rs
+++ b/ext/crypto/ed25519.rs
@@ -2,8 +2,6 @@
 
 use base64::prelude::BASE64_URL_SAFE_NO_PAD;
 use base64::Engine;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 use elliptic_curve::pkcs8::PrivateKeyInfo;
@@ -15,6 +13,16 @@ use spki::der::asn1::BitString;
 use spki::der::Decode;
 use spki::der::Encode;
 
+#[derive(Debug, thiserror::Error)]
+pub enum Ed25519Error {
+  #[error("Failed to export key")]
+  FailedExport,
+  #[error(transparent)]
+  Der(#[from] rsa::pkcs1::der::Error),
+  #[error(transparent)]
+  KeyRejected(#[from] ring::error::KeyRejected),
+}
+
 #[op2(fast)]
 pub fn op_crypto_generate_ed25519_keypair(
   #[buffer] pkey: &mut [u8],
@@ -116,7 +124,7 @@ pub fn op_crypto_import_pkcs8_ed25519(
 #[serde]
 pub fn op_crypto_export_spki_ed25519(
   #[buffer] pubkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Ed25519Error> {
   let key_info = spki::SubjectPublicKeyInfo {
     algorithm: spki::AlgorithmIdentifierOwned {
       // id-Ed25519
@@ -128,9 +136,7 @@ pub fn op_crypto_export_spki_ed25519(
   Ok(
     key_info
       .to_der()
-      .map_err(|_| {
-        custom_error("DOMExceptionOperationError", "Failed to export key")
-      })?
+      .map_err(|_| Ed25519Error::FailedExport)?
       .into(),
   )
 }
@@ -139,7 +145,7 @@ pub fn op_crypto_export_spki_ed25519(
 #[serde]
 pub fn op_crypto_export_pkcs8_ed25519(
   #[buffer] pkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Ed25519Error> {
   use rsa::pkcs1::der::Encode;
 
   // This should probably use OneAsymmetricKey instead
@@ -164,7 +170,7 @@ pub fn op_crypto_export_pkcs8_ed25519(
 #[string]
 pub fn op_crypto_jwk_x_ed25519(
   #[buffer] pkey: &[u8],
-) -> Result<String, AnyError> {
+) -> Result<String, Ed25519Error> {
   let pair = Ed25519KeyPair::from_seed_unchecked(pkey)?;
   Ok(BASE64_URL_SAFE_NO_PAD.encode(pair.public_key().as_ref()))
 }
diff --git a/ext/crypto/encrypt.rs b/ext/crypto/encrypt.rs
index 204648e892..66b27657f8 100644
--- a/ext/crypto/encrypt.rs
+++ b/ext/crypto/encrypt.rs
@@ -16,8 +16,6 @@ use aes_gcm::Nonce;
 use ctr::Ctr128BE;
 use ctr::Ctr32BE;
 use ctr::Ctr64BE;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::unsync::spawn_blocking;
 use deno_core::JsBuffer;
@@ -73,12 +71,30 @@ pub enum EncryptAlgorithm {
   },
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum EncryptError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error("invalid length")]
+  InvalidLength,
+  #[error("invalid key or iv")]
+  InvalidKeyOrIv,
+  #[error("iv length not equal to 12 or 16")]
+  InvalidIvLength,
+  #[error("invalid counter length. Currently supported 32/64/128 bits")]
+  InvalidCounterLength,
+  #[error("tried to encrypt too much data")]
+  TooMuchData,
+  #[error("Encryption failed")]
+  Failed,
+}
+
 #[op2(async)]
 #[serde]
 pub async fn op_crypto_encrypt(
   #[serde] opts: EncryptOptions,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, EncryptError> {
   let key = opts.key;
   let fun = move || match opts.algorithm {
     EncryptAlgorithm::RsaOaep { hash, label } => {
@@ -108,12 +124,12 @@ fn encrypt_rsa_oaep(
   hash: ShaHash,
   label: Vec<u8>,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, EncryptError> {
   let label = String::from_utf8_lossy(&label).to_string();
 
   let public_key = key.as_rsa_public_key()?;
   let public_key = rsa::RsaPublicKey::from_pkcs1_der(&public_key)
-    .map_err(|_| operation_error("failed to decode public key"))?;
+    .map_err(|_| SharedError::FailedDecodePublicKey)?;
   let mut rng = OsRng;
   let padding = match hash {
     ShaHash::Sha1 => rsa::Oaep {
@@ -139,7 +155,7 @@ fn encrypt_rsa_oaep(
   };
   let encrypted = public_key
     .encrypt(&mut rng, padding, data)
-    .map_err(|_| operation_error("Encryption failed"))?;
+    .map_err(|_| EncryptError::Failed)?;
   Ok(encrypted)
 }
 
@@ -148,7 +164,7 @@ fn encrypt_aes_cbc(
   length: usize,
   iv: Vec<u8>,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, EncryptError> {
   let key = key.as_secret_key()?;
   let ciphertext = match length {
     128 => {
@@ -156,7 +172,7 @@ fn encrypt_aes_cbc(
       type Aes128CbcEnc = cbc::Encryptor<aes::Aes128>;
 
       let cipher = Aes128CbcEnc::new_from_slices(key, &iv)
-        .map_err(|_| operation_error("invalid key or iv".to_string()))?;
+        .map_err(|_| EncryptError::InvalidKeyOrIv)?;
       cipher.encrypt_padded_vec_mut::<Pkcs7>(data)
     }
     192 => {
@@ -164,7 +180,7 @@ fn encrypt_aes_cbc(
       type Aes192CbcEnc = cbc::Encryptor<aes::Aes192>;
 
       let cipher = Aes192CbcEnc::new_from_slices(key, &iv)
-        .map_err(|_| operation_error("invalid key or iv".to_string()))?;
+        .map_err(|_| EncryptError::InvalidKeyOrIv)?;
       cipher.encrypt_padded_vec_mut::<Pkcs7>(data)
     }
     256 => {
@@ -172,10 +188,10 @@ fn encrypt_aes_cbc(
       type Aes256CbcEnc = cbc::Encryptor<aes::Aes256>;
 
       let cipher = Aes256CbcEnc::new_from_slices(key, &iv)
-        .map_err(|_| operation_error("invalid key or iv".to_string()))?;
+        .map_err(|_| EncryptError::InvalidKeyOrIv)?;
       cipher.encrypt_padded_vec_mut::<Pkcs7>(data)
     }
-    _ => return Err(type_error("invalid length")),
+    _ => return Err(EncryptError::InvalidLength),
   };
   Ok(ciphertext)
 }
@@ -186,31 +202,31 @@ fn encrypt_aes_gcm_general<N: ArrayLength<u8>>(
   length: usize,
   ciphertext: &mut [u8],
   additional_data: Vec<u8>,
-) -> Result<aes_gcm::Tag, AnyError> {
+) -> Result<aes_gcm::Tag, EncryptError> {
   let nonce = Nonce::<N>::from_slice(&iv);
   let tag = match length {
     128 => {
       let cipher = aes_gcm::AesGcm::<Aes128, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Encryption failed"))?;
+        .map_err(|_| EncryptError::Failed)?;
       cipher
         .encrypt_in_place_detached(nonce, &additional_data, ciphertext)
-        .map_err(|_| operation_error("Encryption failed"))?
+        .map_err(|_| EncryptError::Failed)?
     }
     192 => {
       let cipher = aes_gcm::AesGcm::<Aes192, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Encryption failed"))?;
+        .map_err(|_| EncryptError::Failed)?;
       cipher
         .encrypt_in_place_detached(nonce, &additional_data, ciphertext)
-        .map_err(|_| operation_error("Encryption failed"))?
+        .map_err(|_| EncryptError::Failed)?
     }
     256 => {
       let cipher = aes_gcm::AesGcm::<Aes256, N>::new_from_slice(key)
-        .map_err(|_| operation_error("Encryption failed"))?;
+        .map_err(|_| EncryptError::Failed)?;
       cipher
         .encrypt_in_place_detached(nonce, &additional_data, ciphertext)
-        .map_err(|_| operation_error("Encryption failed"))?
+        .map_err(|_| EncryptError::Failed)?
     }
-    _ => return Err(type_error("invalid length")),
+    _ => return Err(EncryptError::InvalidLength),
   };
 
   Ok(tag)
@@ -223,7 +239,7 @@ fn encrypt_aes_gcm(
   iv: Vec<u8>,
   additional_data: Option<Vec<u8>>,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, EncryptError> {
   let key = key.as_secret_key()?;
   let additional_data = additional_data.unwrap_or_default();
 
@@ -244,7 +260,7 @@ fn encrypt_aes_gcm(
       &mut ciphertext,
       additional_data,
     )?,
-    _ => return Err(type_error("iv length not equal to 12 or 16")),
+    _ => return Err(EncryptError::InvalidIvLength),
   };
 
   // Truncated tag to the specified tag length.
@@ -261,7 +277,7 @@ fn encrypt_aes_ctr_gen<B>(
   key: &[u8],
   counter: &[u8],
   data: &[u8],
-) -> Result<Vec<u8>, AnyError>
+) -> Result<Vec<u8>, EncryptError>
 where
   B: KeyIvInit + StreamCipher,
 {
@@ -270,7 +286,7 @@ where
   let mut ciphertext = data.to_vec();
   cipher
     .try_apply_keystream(&mut ciphertext)
-    .map_err(|_| operation_error("tried to encrypt too much data"))?;
+    .map_err(|_| EncryptError::TooMuchData)?;
 
   Ok(ciphertext)
 }
@@ -281,7 +297,7 @@ fn encrypt_aes_ctr(
   counter: &[u8],
   ctr_length: usize,
   data: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, EncryptError> {
   let key = key.as_secret_key()?;
 
   match ctr_length {
@@ -289,22 +305,20 @@ fn encrypt_aes_ctr(
       128 => encrypt_aes_ctr_gen::<Ctr32BE<aes::Aes128>>(key, counter, data),
       192 => encrypt_aes_ctr_gen::<Ctr32BE<aes::Aes192>>(key, counter, data),
       256 => encrypt_aes_ctr_gen::<Ctr32BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(EncryptError::InvalidLength),
     },
     64 => match key_length {
       128 => encrypt_aes_ctr_gen::<Ctr64BE<aes::Aes128>>(key, counter, data),
       192 => encrypt_aes_ctr_gen::<Ctr64BE<aes::Aes192>>(key, counter, data),
       256 => encrypt_aes_ctr_gen::<Ctr64BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(EncryptError::InvalidLength),
     },
     128 => match key_length {
       128 => encrypt_aes_ctr_gen::<Ctr128BE<aes::Aes128>>(key, counter, data),
       192 => encrypt_aes_ctr_gen::<Ctr128BE<aes::Aes192>>(key, counter, data),
       256 => encrypt_aes_ctr_gen::<Ctr128BE<aes::Aes256>>(key, counter, data),
-      _ => Err(type_error("invalid length")),
+      _ => Err(EncryptError::InvalidLength),
     },
-    _ => Err(type_error(
-      "invalid counter length. Currently supported 32/64/128 bits",
-    )),
+    _ => Err(EncryptError::InvalidCounterLength),
   }
 }
diff --git a/ext/crypto/export_key.rs b/ext/crypto/export_key.rs
index 00ce7e11c6..edf0d7239c 100644
--- a/ext/crypto/export_key.rs
+++ b/ext/crypto/export_key.rs
@@ -4,8 +4,6 @@ use base64::prelude::BASE64_URL_SAFE_NO_PAD;
 use base64::Engine;
 use const_oid::AssociatedOid;
 use const_oid::ObjectIdentifier;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 use elliptic_curve::sec1::ToEncodedPoint;
@@ -22,6 +20,16 @@ use spki::AlgorithmIdentifierOwned;
 
 use crate::shared::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum ExportKeyError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error(transparent)]
+  Der(#[from] spki::der::Error),
+  #[error("Unsupported named curve")]
+  UnsupportedNamedCurve,
+}
+
 #[derive(Deserialize)]
 #[serde(rename_all = "camelCase")]
 pub struct ExportKeyOptions {
@@ -99,7 +107,7 @@ pub enum ExportKeyResult {
 pub fn op_crypto_export_key(
   #[serde] opts: ExportKeyOptions,
   #[serde] key_data: V8RawKeyData,
-) -> Result<ExportKeyResult, AnyError> {
+) -> Result<ExportKeyResult, ExportKeyError> {
   match opts.algorithm {
     ExportKeyAlgorithm::RsassaPkcs1v15 {}
     | ExportKeyAlgorithm::RsaPss {}
@@ -125,7 +133,7 @@ fn bytes_to_b64(bytes: &[u8]) -> String {
 fn export_key_rsa(
   format: ExportKeyFormat,
   key_data: V8RawKeyData,
-) -> Result<ExportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ExportKeyResult, ExportKeyError> {
   match format {
     ExportKeyFormat::Spki => {
       let subject_public_key = &key_data.as_rsa_public_key()?;
@@ -181,12 +189,7 @@ fn export_key_rsa(
     ExportKeyFormat::JwkPublic => {
       let public_key = key_data.as_rsa_public_key()?;
       let public_key = rsa::pkcs1::RsaPublicKey::from_der(&public_key)
-        .map_err(|_| {
-          custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode public key",
-          )
-        })?;
+        .map_err(|_| SharedError::FailedDecodePublicKey)?;
 
       Ok(ExportKeyResult::JwkPublicRsa {
         n: uint_to_b64(public_key.modulus),
@@ -196,12 +199,7 @@ fn export_key_rsa(
     ExportKeyFormat::JwkPrivate => {
       let private_key = key_data.as_rsa_private_key()?;
       let private_key = rsa::pkcs1::RsaPrivateKey::from_der(private_key)
-        .map_err(|_| {
-          custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode private key",
-          )
-        })?;
+        .map_err(|_| SharedError::FailedDecodePrivateKey)?;
 
       Ok(ExportKeyResult::JwkPrivateRsa {
         n: uint_to_b64(private_key.modulus),
@@ -214,14 +212,14 @@ fn export_key_rsa(
         qi: uint_to_b64(private_key.coefficient),
       })
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
 fn export_key_symmetric(
   format: ExportKeyFormat,
   key_data: V8RawKeyData,
-) -> Result<ExportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ExportKeyResult, ExportKeyError> {
   match format {
     ExportKeyFormat::JwkSecret => {
       let bytes = key_data.as_secret_key()?;
@@ -230,7 +228,7 @@ fn export_key_symmetric(
         k: bytes_to_b64(bytes),
       })
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
@@ -239,7 +237,7 @@ fn export_key_ec(
   key_data: V8RawKeyData,
   algorithm: ExportKeyAlgorithm,
   named_curve: EcNamedCurve,
-) -> Result<ExportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ExportKeyResult, ExportKeyError> {
   match format {
     ExportKeyFormat::Raw => {
       let subject_public_key = match named_curve {
@@ -332,10 +330,7 @@ fn export_key_ec(
             y: bytes_to_b64(y),
           })
         } else {
-          Err(custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode public key",
-          ))
+          Err(SharedError::FailedDecodePublicKey.into())
         }
       }
       EcNamedCurve::P384 => {
@@ -350,10 +345,7 @@ fn export_key_ec(
             y: bytes_to_b64(y),
           })
         } else {
-          Err(custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode public key",
-          ))
+          Err(SharedError::FailedDecodePublicKey.into())
         }
       }
       EcNamedCurve::P521 => {
@@ -368,10 +360,7 @@ fn export_key_ec(
             y: bytes_to_b64(y),
           })
         } else {
-          Err(custom_error(
-            "DOMExceptionOperationError",
-            "failed to decode public key",
-          ))
+          Err(SharedError::FailedDecodePublicKey.into())
         }
       }
     },
@@ -380,13 +369,8 @@ fn export_key_ec(
 
       match named_curve {
         EcNamedCurve::P256 => {
-          let ec_key =
-            p256::SecretKey::from_pkcs8_der(private_key).map_err(|_| {
-              custom_error(
-                "DOMExceptionOperationError",
-                "failed to decode private key",
-              )
-            })?;
+          let ec_key = p256::SecretKey::from_pkcs8_der(private_key)
+            .map_err(|_| SharedError::FailedDecodePrivateKey)?;
 
           let point = ec_key.public_key().to_encoded_point(false);
           if let elliptic_curve::sec1::Coordinates::Uncompressed { x, y } =
@@ -398,18 +382,13 @@ fn export_key_ec(
               d: bytes_to_b64(&ec_key.to_bytes()),
             })
           } else {
-            Err(data_error("expected valid public EC key"))
+            Err(SharedError::ExpectedValidPublicECKey.into())
           }
         }
 
         EcNamedCurve::P384 => {
-          let ec_key =
-            p384::SecretKey::from_pkcs8_der(private_key).map_err(|_| {
-              custom_error(
-                "DOMExceptionOperationError",
-                "failed to decode private key",
-              )
-            })?;
+          let ec_key = p384::SecretKey::from_pkcs8_der(private_key)
+            .map_err(|_| SharedError::FailedDecodePrivateKey)?;
 
           let point = ec_key.public_key().to_encoded_point(false);
           if let elliptic_curve::sec1::Coordinates::Uncompressed { x, y } =
@@ -421,12 +400,12 @@ fn export_key_ec(
               d: bytes_to_b64(&ec_key.to_bytes()),
             })
           } else {
-            Err(data_error("expected valid public EC key"))
+            Err(SharedError::ExpectedValidPublicECKey.into())
           }
         }
-        _ => Err(not_supported_error("Unsupported namedCurve")),
+        _ => Err(ExportKeyError::UnsupportedNamedCurve),
       }
     }
-    ExportKeyFormat::JwkSecret => Err(unsupported_format()),
+    ExportKeyFormat::JwkSecret => Err(SharedError::UnsupportedFormat.into()),
   }
 }
diff --git a/ext/crypto/generate_key.rs b/ext/crypto/generate_key.rs
index 43aea2c705..3c0bd77c22 100644
--- a/ext/crypto/generate_key.rs
+++ b/ext/crypto/generate_key.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::unsync::spawn_blocking;
 use deno_core::ToJsBuffer;
@@ -16,6 +15,26 @@ use serde::Deserialize;
 
 use crate::shared::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum GenerateKeyError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error("Bad public exponent")]
+  BadPublicExponent,
+  #[error("Invalid HMAC key length")]
+  InvalidHMACKeyLength,
+  #[error("Failed to serialize RSA key")]
+  FailedRSAKeySerialization,
+  #[error("Invalid AES key length")]
+  InvalidAESKeyLength,
+  #[error("Failed to generate RSA key")]
+  FailedRSAKeyGeneration,
+  #[error("Failed to generate EC key")]
+  FailedECKeyGeneration,
+  #[error("Failed to generate key")]
+  FailedKeyGeneration,
+}
+
 // Allowlist for RSA public exponents.
 static PUB_EXPONENT_1: Lazy<BigUint> =
   Lazy::new(|| BigUint::from_u64(3).unwrap());
@@ -46,7 +65,7 @@ pub enum GenerateKeyOptions {
 #[serde]
 pub async fn op_crypto_generate_key(
   #[serde] opts: GenerateKeyOptions,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, GenerateKeyError> {
   let fun = || match opts {
     GenerateKeyOptions::Rsa {
       modulus_length,
@@ -65,21 +84,21 @@ pub async fn op_crypto_generate_key(
 fn generate_key_rsa(
   modulus_length: u32,
   public_exponent: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, GenerateKeyError> {
   let exponent = BigUint::from_bytes_be(public_exponent);
   if exponent != *PUB_EXPONENT_1 && exponent != *PUB_EXPONENT_2 {
-    return Err(operation_error("Bad public exponent"));
+    return Err(GenerateKeyError::BadPublicExponent);
   }
 
   let mut rng = OsRng;
 
   let private_key =
     RsaPrivateKey::new_with_exp(&mut rng, modulus_length as usize, &exponent)
-      .map_err(|_| operation_error("Failed to generate RSA key"))?;
+      .map_err(|_| GenerateKeyError::FailedRSAKeyGeneration)?;
 
   let private_key = private_key
     .to_pkcs1_der()
-    .map_err(|_| operation_error("Failed to serialize RSA key"))?;
+    .map_err(|_| GenerateKeyError::FailedRSAKeySerialization)?;
 
   Ok(private_key.as_bytes().to_vec())
 }
@@ -90,7 +109,9 @@ fn generate_key_ec_p521() -> Vec<u8> {
   key.to_nonzero_scalar().to_bytes().to_vec()
 }
 
-fn generate_key_ec(named_curve: EcNamedCurve) -> Result<Vec<u8>, AnyError> {
+fn generate_key_ec(
+  named_curve: EcNamedCurve,
+) -> Result<Vec<u8>, GenerateKeyError> {
   let curve = match named_curve {
     EcNamedCurve::P256 => &ring::signature::ECDSA_P256_SHA256_FIXED_SIGNING,
     EcNamedCurve::P384 => &ring::signature::ECDSA_P384_SHA384_FIXED_SIGNING,
@@ -100,21 +121,21 @@ fn generate_key_ec(named_curve: EcNamedCurve) -> Result<Vec<u8>, AnyError> {
   let rng = ring::rand::SystemRandom::new();
 
   let pkcs8 = EcdsaKeyPair::generate_pkcs8(curve, &rng)
-    .map_err(|_| operation_error("Failed to generate EC key"))?;
+    .map_err(|_| GenerateKeyError::FailedECKeyGeneration)?;
 
   Ok(pkcs8.as_ref().to_vec())
 }
 
-fn generate_key_aes(length: usize) -> Result<Vec<u8>, AnyError> {
+fn generate_key_aes(length: usize) -> Result<Vec<u8>, GenerateKeyError> {
   if length % 8 != 0 || length > 256 {
-    return Err(operation_error("Invalid AES key length"));
+    return Err(GenerateKeyError::InvalidAESKeyLength);
   }
 
   let mut key = vec![0u8; length / 8];
   let rng = ring::rand::SystemRandom::new();
   rng
     .fill(&mut key)
-    .map_err(|_| operation_error("Failed to generate key"))?;
+    .map_err(|_| GenerateKeyError::FailedKeyGeneration)?;
 
   Ok(key)
 }
@@ -122,7 +143,7 @@ fn generate_key_aes(length: usize) -> Result<Vec<u8>, AnyError> {
 fn generate_key_hmac(
   hash: ShaHash,
   length: Option<usize>,
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, GenerateKeyError> {
   let hash = match hash {
     ShaHash::Sha1 => &ring::hmac::HMAC_SHA1_FOR_LEGACY_USE_ONLY,
     ShaHash::Sha256 => &ring::hmac::HMAC_SHA256,
@@ -132,12 +153,12 @@ fn generate_key_hmac(
 
   let length = if let Some(length) = length {
     if length % 8 != 0 {
-      return Err(operation_error("Invalid HMAC key length"));
+      return Err(GenerateKeyError::InvalidHMACKeyLength);
     }
 
     let length = length / 8;
     if length > ring::digest::MAX_BLOCK_LEN {
-      return Err(operation_error("Invalid HMAC key length"));
+      return Err(GenerateKeyError::InvalidHMACKeyLength);
     }
 
     length
@@ -149,7 +170,7 @@ fn generate_key_hmac(
   let mut key = vec![0u8; length];
   rng
     .fill(&mut key)
-    .map_err(|_| operation_error("Failed to generate key"))?;
+    .map_err(|_| GenerateKeyError::FailedKeyGeneration)?;
 
   Ok(key)
 }
diff --git a/ext/crypto/import_key.rs b/ext/crypto/import_key.rs
index e30baea03a..3463ca2beb 100644
--- a/ext/crypto/import_key.rs
+++ b/ext/crypto/import_key.rs
@@ -1,7 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use base64::Engine;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::JsBuffer;
 use deno_core::ToJsBuffer;
@@ -15,6 +14,70 @@ use spki::der::Decode;
 
 use crate::shared::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum ImportKeyError {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error("invalid modulus")]
+  InvalidModulus,
+  #[error("invalid public exponent")]
+  InvalidPublicExponent,
+  #[error("invalid private exponent")]
+  InvalidPrivateExponent,
+  #[error("invalid first prime factor")]
+  InvalidFirstPrimeFactor,
+  #[error("invalid second prime factor")]
+  InvalidSecondPrimeFactor,
+  #[error("invalid first CRT exponent")]
+  InvalidFirstCRTExponent,
+  #[error("invalid second CRT exponent")]
+  InvalidSecondCRTExponent,
+  #[error("invalid CRT coefficient")]
+  InvalidCRTCoefficient,
+  #[error("invalid b64 coordinate")]
+  InvalidB64Coordinate,
+  #[error("invalid RSA public key")]
+  InvalidRSAPublicKey,
+  #[error("invalid RSA private key")]
+  InvalidRSAPrivateKey,
+  #[error("unsupported algorithm")]
+  UnsupportedAlgorithm,
+  #[error("public key is invalid (too long)")]
+  PublicKeyTooLong,
+  #[error("private key is invalid (too long)")]
+  PrivateKeyTooLong,
+  #[error("invalid P-256 elliptic curve point")]
+  InvalidP256ECPoint,
+  #[error("invalid P-384 elliptic curve point")]
+  InvalidP384ECPoint,
+  #[error("invalid P-521 elliptic curve point")]
+  InvalidP521ECPoint,
+  #[error("invalid P-256 elliptic curve SPKI data")]
+  InvalidP256ECSPKIData,
+  #[error("invalid P-384 elliptic curve SPKI data")]
+  InvalidP384ECSPKIData,
+  #[error("invalid P-521 elliptic curve SPKI data")]
+  InvalidP521ECSPKIData,
+  #[error("curve mismatch")]
+  CurveMismatch,
+  #[error("Unsupported named curve")]
+  UnsupportedNamedCurve,
+  #[error("invalid key data")]
+  InvalidKeyData,
+  #[error("invalid JWK private key")]
+  InvalidJWKPrivateKey,
+  #[error(transparent)]
+  EllipticCurve(#[from] elliptic_curve::Error),
+  #[error("expected valid PKCS#8 data")]
+  ExpectedValidPkcs8Data,
+  #[error("malformed parameters")]
+  MalformedParameters,
+  #[error(transparent)]
+  Spki(#[from] spki::Error),
+  #[error(transparent)]
+  Der(#[from] rsa::pkcs1::der::Error),
+}
+
 #[derive(Deserialize)]
 #[serde(rename_all = "camelCase")]
 pub enum KeyData {
@@ -93,7 +156,7 @@ pub enum ImportKeyResult {
 pub fn op_crypto_import_key(
   #[serde] opts: ImportKeyOptions,
   #[serde] key_data: KeyData,
-) -> Result<ImportKeyResult, AnyError> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match opts {
     ImportKeyOptions::RsassaPkcs1v15 {} => import_key_rsassa(key_data),
     ImportKeyOptions::RsaPss {} => import_key_rsapss(key_data),
@@ -117,21 +180,21 @@ const BASE64_URL_SAFE_FORGIVING:
   );
 
 macro_rules! jwt_b64_int_or_err {
-  ($name:ident, $b64:expr, $err:expr) => {
+  ($name:ident, $b64:expr, $err:tt) => {
     let bytes = BASE64_URL_SAFE_FORGIVING
       .decode($b64)
-      .map_err(|_| data_error($err))?;
-    let $name = UintRef::new(&bytes).map_err(|_| data_error($err))?;
+      .map_err(|_| ImportKeyError::$err)?;
+    let $name = UintRef::new(&bytes).map_err(|_| ImportKeyError::$err)?;
   };
 }
 
 fn import_key_rsa_jwk(
   key_data: KeyData,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::JwkPublicRsa { n, e } => {
-      jwt_b64_int_or_err!(modulus, &n, "invalid modulus");
-      jwt_b64_int_or_err!(public_exponent, &e, "invalid public exponent");
+      jwt_b64_int_or_err!(modulus, &n, InvalidModulus);
+      jwt_b64_int_or_err!(public_exponent, &e, InvalidPublicExponent);
 
       let public_key = rsa::pkcs1::RsaPublicKey {
         modulus,
@@ -141,7 +204,7 @@ fn import_key_rsa_jwk(
       let mut data = Vec::new();
       public_key
         .encode_to_vec(&mut data)
-        .map_err(|_| data_error("invalid rsa public key"))?;
+        .map_err(|_| ImportKeyError::InvalidRSAPublicKey)?;
 
       let public_exponent =
         public_key.public_exponent.as_bytes().to_vec().into();
@@ -163,14 +226,14 @@ fn import_key_rsa_jwk(
       dq,
       qi,
     } => {
-      jwt_b64_int_or_err!(modulus, &n, "invalid modulus");
-      jwt_b64_int_or_err!(public_exponent, &e, "invalid public exponent");
-      jwt_b64_int_or_err!(private_exponent, &d, "invalid private exponent");
-      jwt_b64_int_or_err!(prime1, &p, "invalid first prime factor");
-      jwt_b64_int_or_err!(prime2, &q, "invalid second prime factor");
-      jwt_b64_int_or_err!(exponent1, &dp, "invalid first CRT exponent");
-      jwt_b64_int_or_err!(exponent2, &dq, "invalid second CRT exponent");
-      jwt_b64_int_or_err!(coefficient, &qi, "invalid CRT coefficient");
+      jwt_b64_int_or_err!(modulus, &n, InvalidModulus);
+      jwt_b64_int_or_err!(public_exponent, &e, InvalidPublicExponent);
+      jwt_b64_int_or_err!(private_exponent, &d, InvalidPrivateExponent);
+      jwt_b64_int_or_err!(prime1, &p, InvalidFirstPrimeFactor);
+      jwt_b64_int_or_err!(prime2, &q, InvalidSecondPrimeFactor);
+      jwt_b64_int_or_err!(exponent1, &dp, InvalidFirstCRTExponent);
+      jwt_b64_int_or_err!(exponent2, &dq, InvalidSecondCRTExponent);
+      jwt_b64_int_or_err!(coefficient, &qi, InvalidCRTCoefficient);
 
       let private_key = rsa::pkcs1::RsaPrivateKey {
         modulus,
@@ -187,7 +250,7 @@ fn import_key_rsa_jwk(
       let mut data = Vec::new();
       private_key
         .encode_to_vec(&mut data)
-        .map_err(|_| data_error("invalid rsa private key"))?;
+        .map_err(|_| ImportKeyError::InvalidRSAPrivateKey)?;
 
       let public_exponent =
         private_key.public_exponent.as_bytes().to_vec().into();
@@ -205,37 +268,33 @@ fn import_key_rsa_jwk(
 
 fn import_key_rsassa(
   key_data: KeyData,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::Spki(data) => {
       // 2-3.
-      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let public_key = rsa::pkcs1::RsaPublicKey::from_der(
         pk_info.subject_public_key.raw_bytes(),
-      )
-      .map_err(|e| data_error(e.to_string()))?;
+      )?;
 
-      let bytes_consumed = public_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = public_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(
           pk_info.subject_public_key.raw_bytes().len() as u16,
         )
       {
-        return Err(data_error("public key is invalid (too long)"));
+        return Err(ImportKeyError::PublicKeyTooLong);
       }
 
       let data = pk_info.subject_public_key.raw_bytes().to_vec().into();
@@ -251,30 +310,26 @@ fn import_key_rsassa(
     }
     KeyData::Pkcs8(data) => {
       // 2-3.
-      let pk_info = PrivateKeyInfo::from_der(&data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = PrivateKeyInfo::from_der(&data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let private_key =
-        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)
-          .map_err(|e| data_error(e.to_string()))?;
+        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)?;
 
-      let bytes_consumed = private_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = private_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(pk_info.private_key.len() as u16)
       {
-        return Err(data_error("private key is invalid (too long)"));
+        return Err(ImportKeyError::PrivateKeyTooLong);
       }
 
       let data = pk_info.private_key.to_vec().into();
@@ -291,43 +346,39 @@ fn import_key_rsassa(
     KeyData::JwkPublicRsa { .. } | KeyData::JwkPrivateRsa { .. } => {
       import_key_rsa_jwk(key_data)
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
 fn import_key_rsapss(
   key_data: KeyData,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::Spki(data) => {
       // 2-3.
-      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let public_key = rsa::pkcs1::RsaPublicKey::from_der(
         pk_info.subject_public_key.raw_bytes(),
-      )
-      .map_err(|e| data_error(e.to_string()))?;
+      )?;
 
-      let bytes_consumed = public_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = public_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(
           pk_info.subject_public_key.raw_bytes().len() as u16,
         )
       {
-        return Err(data_error("public key is invalid (too long)"));
+        return Err(ImportKeyError::PublicKeyTooLong);
       }
 
       let data = pk_info.subject_public_key.raw_bytes().to_vec().into();
@@ -343,30 +394,26 @@ fn import_key_rsapss(
     }
     KeyData::Pkcs8(data) => {
       // 2-3.
-      let pk_info = PrivateKeyInfo::from_der(&data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = PrivateKeyInfo::from_der(&data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let private_key =
-        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)
-          .map_err(|e| data_error(e.to_string()))?;
+        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)?;
 
-      let bytes_consumed = private_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = private_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(pk_info.private_key.len() as u16)
       {
-        return Err(data_error("private key is invalid (too long)"));
+        return Err(ImportKeyError::PrivateKeyTooLong);
       }
 
       let data = pk_info.private_key.to_vec().into();
@@ -383,43 +430,39 @@ fn import_key_rsapss(
     KeyData::JwkPublicRsa { .. } | KeyData::JwkPrivateRsa { .. } => {
       import_key_rsa_jwk(key_data)
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
 fn import_key_rsaoaep(
   key_data: KeyData,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::Spki(data) => {
       // 2-3.
-      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let public_key = rsa::pkcs1::RsaPublicKey::from_der(
         pk_info.subject_public_key.raw_bytes(),
-      )
-      .map_err(|e| data_error(e.to_string()))?;
+      )?;
 
-      let bytes_consumed = public_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = public_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(
           pk_info.subject_public_key.raw_bytes().len() as u16,
         )
       {
-        return Err(data_error("public key is invalid (too long)"));
+        return Err(ImportKeyError::PublicKeyTooLong);
       }
 
       let data = pk_info.subject_public_key.raw_bytes().to_vec().into();
@@ -435,30 +478,26 @@ fn import_key_rsaoaep(
     }
     KeyData::Pkcs8(data) => {
       // 2-3.
-      let pk_info = PrivateKeyInfo::from_der(&data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = PrivateKeyInfo::from_der(&data)?;
 
       // 4-5.
       let alg = pk_info.algorithm.oid;
 
       // 6-7. (skipped, only support rsaEncryption for interoperability)
       if alg != RSA_ENCRYPTION_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 8-9.
       let private_key =
-        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)
-          .map_err(|e| data_error(e.to_string()))?;
+        rsa::pkcs1::RsaPrivateKey::from_der(pk_info.private_key)?;
 
-      let bytes_consumed = private_key
-        .encoded_len()
-        .map_err(|e| data_error(e.to_string()))?;
+      let bytes_consumed = private_key.encoded_len()?;
 
       if bytes_consumed
         != rsa::pkcs1::der::Length::new(pk_info.private_key.len() as u16)
       {
-        return Err(data_error("private key is invalid (too long)"));
+        return Err(ImportKeyError::PrivateKeyTooLong);
       }
 
       let data = pk_info.private_key.to_vec().into();
@@ -475,14 +514,14 @@ fn import_key_rsaoaep(
     KeyData::JwkPublicRsa { .. } | KeyData::JwkPrivateRsa { .. } => {
       import_key_rsa_jwk(key_data)
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
 fn decode_b64url_to_field_bytes<C: elliptic_curve::Curve>(
   b64: &str,
-) -> Result<elliptic_curve::FieldBytes<C>, deno_core::anyhow::Error> {
-  jwt_b64_int_or_err!(val, b64, "invalid b64 coordinate");
+) -> Result<elliptic_curve::FieldBytes<C>, ImportKeyError> {
+  jwt_b64_int_or_err!(val, b64, InvalidB64Coordinate);
 
   let mut bytes = elliptic_curve::FieldBytes::<C>::default();
   let original_bytes = val.as_bytes();
@@ -495,7 +534,7 @@ fn decode_b64url_to_field_bytes<C: elliptic_curve::Curve>(
   let val = new_bytes.as_slice();
 
   if val.len() != bytes.len() {
-    return Err(data_error("invalid b64 coordinate"));
+    return Err(ImportKeyError::InvalidB64Coordinate);
   }
   bytes.copy_from_slice(val);
 
@@ -506,7 +545,7 @@ fn import_key_ec_jwk_to_point(
   x: String,
   y: String,
   named_curve: EcNamedCurve,
-) -> Result<Vec<u8>, deno_core::anyhow::Error> {
+) -> Result<Vec<u8>, ImportKeyError> {
   let point_bytes = match named_curve {
     EcNamedCurve::P256 => {
       let x = decode_b64url_to_field_bytes::<p256::NistP256>(&x)?;
@@ -534,7 +573,7 @@ fn import_key_ec_jwk_to_point(
 fn import_key_ec_jwk(
   key_data: KeyData,
   named_curve: EcNamedCurve,
-) -> Result<ImportKeyResult, deno_core::anyhow::Error> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::JwkPublicEc { x, y } => {
       let point_bytes = import_key_ec_jwk_to_point(x, y, named_curve)?;
@@ -550,21 +589,21 @@ fn import_key_ec_jwk(
           let pk = p256::SecretKey::from_bytes(&d)?;
 
           pk.to_pkcs8_der()
-            .map_err(|_| data_error("invalid JWK private key"))?
+            .map_err(|_| ImportKeyError::InvalidJWKPrivateKey)?
         }
         EcNamedCurve::P384 => {
           let d = decode_b64url_to_field_bytes::<p384::NistP384>(&d)?;
           let pk = p384::SecretKey::from_bytes(&d)?;
 
           pk.to_pkcs8_der()
-            .map_err(|_| data_error("invalid JWK private key"))?
+            .map_err(|_| ImportKeyError::InvalidJWKPrivateKey)?
         }
         EcNamedCurve::P521 => {
           let d = decode_b64url_to_field_bytes::<p521::NistP521>(&d)?;
           let pk = p521::SecretKey::from_bytes(&d)?;
 
           pk.to_pkcs8_der()
-            .map_err(|_| data_error("invalid JWK private key"))?
+            .map_err(|_| ImportKeyError::InvalidJWKPrivateKey)?
         }
       };
 
@@ -595,7 +634,7 @@ impl<'a> TryFrom<spki::der::asn1::AnyRef<'a>> for ECParametersSpki {
 fn import_key_ec(
   key_data: KeyData,
   named_curve: EcNamedCurve,
-) -> Result<ImportKeyResult, AnyError> {
+) -> Result<ImportKeyResult, ImportKeyError> {
   match key_data {
     KeyData::Raw(data) => {
       // The point is parsed and validated, ultimately the original data is
@@ -604,28 +643,28 @@ fn import_key_ec(
         EcNamedCurve::P256 => {
           // 1-2.
           let point = p256::EncodedPoint::from_bytes(&data)
-            .map_err(|_| data_error("invalid P-256 elliptic curve point"))?;
+            .map_err(|_| ImportKeyError::InvalidP256ECPoint)?;
           // 3.
           if point.is_identity() {
-            return Err(data_error("invalid P-256 elliptic curve point"));
+            return Err(ImportKeyError::InvalidP256ECPoint);
           }
         }
         EcNamedCurve::P384 => {
           // 1-2.
           let point = p384::EncodedPoint::from_bytes(&data)
-            .map_err(|_| data_error("invalid P-384 elliptic curve point"))?;
+            .map_err(|_| ImportKeyError::InvalidP384ECPoint)?;
           // 3.
           if point.is_identity() {
-            return Err(data_error("invalid P-384 elliptic curve point"));
+            return Err(ImportKeyError::InvalidP384ECPoint);
           }
         }
         EcNamedCurve::P521 => {
           // 1-2.
           let point = p521::EncodedPoint::from_bytes(&data)
-            .map_err(|_| data_error("invalid P-521 elliptic curve point"))?;
+            .map_err(|_| ImportKeyError::InvalidP521ECPoint)?;
           // 3.
           if point.is_identity() {
-            return Err(data_error("invalid P-521 elliptic curve point"));
+            return Err(ImportKeyError::InvalidP521ECPoint);
           }
         }
       };
@@ -635,11 +674,11 @@ fn import_key_ec(
     }
     KeyData::Pkcs8(data) => {
       let pk = PrivateKeyInfo::from_der(data.as_ref())
-        .map_err(|_| data_error("expected valid PKCS#8 data"))?;
+        .map_err(|_| ImportKeyError::ExpectedValidPkcs8Data)?;
       let named_curve_alg = pk
         .algorithm
         .parameters
-        .ok_or_else(|| data_error("malformed parameters"))?
+        .ok_or(ImportKeyError::MalformedParameters)?
         .try_into()
         .unwrap();
 
@@ -654,7 +693,7 @@ fn import_key_ec(
       };
 
       if pk_named_curve != Some(named_curve) {
-        return Err(data_error("curve mismatch"));
+        return Err(ImportKeyError::CurveMismatch);
       }
 
       Ok(ImportKeyResult::Ec {
@@ -663,14 +702,13 @@ fn import_key_ec(
     }
     KeyData::Spki(data) => {
       // 2-3.
-      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)
-        .map_err(|e| data_error(e.to_string()))?;
+      let pk_info = spki::SubjectPublicKeyInfoRef::try_from(&*data)?;
 
       // 4.
       let alg = pk_info.algorithm.oid;
       // id-ecPublicKey
       if alg != elliptic_curve::ALGORITHM_OID {
-        return Err(data_error("unsupported algorithm"));
+        return Err(ImportKeyError::UnsupportedAlgorithm);
       }
 
       // 5-7.
@@ -678,9 +716,9 @@ fn import_key_ec(
         pk_info
           .algorithm
           .parameters
-          .ok_or_else(|| data_error("malformed parameters"))?,
+          .ok_or(ImportKeyError::MalformedParameters)?,
       )
-      .map_err(|_| data_error("malformed parameters"))?;
+      .map_err(|_| ImportKeyError::MalformedParameters)?;
 
       // 8-9.
       let named_curve_alg = params.named_curve_alg;
@@ -704,36 +742,30 @@ fn import_key_ec(
 
         let bytes_consumed = match named_curve {
           EcNamedCurve::P256 => {
-            let point =
-              p256::EncodedPoint::from_bytes(&*encoded_key).map_err(|_| {
-                data_error("invalid P-256 elliptic curve SPKI data")
-              })?;
+            let point = p256::EncodedPoint::from_bytes(&*encoded_key)
+              .map_err(|_| ImportKeyError::InvalidP256ECSPKIData)?;
             if point.is_identity() {
-              return Err(data_error("invalid P-256 elliptic curve point"));
+              return Err(ImportKeyError::InvalidP256ECPoint);
             }
 
             point.as_bytes().len()
           }
           EcNamedCurve::P384 => {
-            let point =
-              p384::EncodedPoint::from_bytes(&*encoded_key).map_err(|_| {
-                data_error("invalid P-384 elliptic curve SPKI data")
-              })?;
+            let point = p384::EncodedPoint::from_bytes(&*encoded_key)
+              .map_err(|_| ImportKeyError::InvalidP384ECSPKIData)?;
 
             if point.is_identity() {
-              return Err(data_error("invalid P-384 elliptic curve point"));
+              return Err(ImportKeyError::InvalidP384ECPoint);
             }
 
             point.as_bytes().len()
           }
           EcNamedCurve::P521 => {
-            let point =
-              p521::EncodedPoint::from_bytes(&*encoded_key).map_err(|_| {
-                data_error("invalid P-521 elliptic curve SPKI data")
-              })?;
+            let point = p521::EncodedPoint::from_bytes(&*encoded_key)
+              .map_err(|_| ImportKeyError::InvalidP521ECSPKIData)?;
 
             if point.is_identity() {
-              return Err(data_error("invalid P-521 elliptic curve point"));
+              return Err(ImportKeyError::InvalidP521ECPoint);
             }
 
             point.as_bytes().len()
@@ -741,15 +773,15 @@ fn import_key_ec(
         };
 
         if bytes_consumed != pk_info.subject_public_key.raw_bytes().len() {
-          return Err(data_error("public key is invalid (too long)"));
+          return Err(ImportKeyError::PublicKeyTooLong);
         }
 
         // 11.
         if named_curve != pk_named_curve {
-          return Err(data_error("curve mismatch"));
+          return Err(ImportKeyError::CurveMismatch);
         }
       } else {
-        return Err(data_error("Unsupported named curve"));
+        return Err(ImportKeyError::UnsupportedNamedCurve);
       }
 
       Ok(ImportKeyResult::Ec {
@@ -759,34 +791,38 @@ fn import_key_ec(
     KeyData::JwkPublicEc { .. } | KeyData::JwkPrivateEc { .. } => {
       import_key_ec_jwk(key_data, named_curve)
     }
-    _ => Err(unsupported_format()),
+    _ => Err(SharedError::UnsupportedFormat.into()),
   }
 }
 
-fn import_key_aes(key_data: KeyData) -> Result<ImportKeyResult, AnyError> {
+fn import_key_aes(
+  key_data: KeyData,
+) -> Result<ImportKeyResult, ImportKeyError> {
   Ok(match key_data {
     KeyData::JwkSecret { k } => {
       let data = BASE64_URL_SAFE_FORGIVING
         .decode(k)
-        .map_err(|_| data_error("invalid key data"))?;
+        .map_err(|_| ImportKeyError::InvalidKeyData)?;
       ImportKeyResult::Hmac {
         raw_data: RustRawKeyData::Secret(data.into()),
       }
     }
-    _ => return Err(unsupported_format()),
+    _ => return Err(SharedError::UnsupportedFormat.into()),
   })
 }
 
-fn import_key_hmac(key_data: KeyData) -> Result<ImportKeyResult, AnyError> {
+fn import_key_hmac(
+  key_data: KeyData,
+) -> Result<ImportKeyResult, ImportKeyError> {
   Ok(match key_data {
     KeyData::JwkSecret { k } => {
       let data = BASE64_URL_SAFE_FORGIVING
         .decode(k)
-        .map_err(|_| data_error("invalid key data"))?;
+        .map_err(|_| ImportKeyError::InvalidKeyData)?;
       ImportKeyResult::Hmac {
         raw_data: RustRawKeyData::Secret(data.into()),
       }
     }
-    _ => return Err(unsupported_format()),
+    _ => return Err(SharedError::UnsupportedFormat.into()),
   })
 }
diff --git a/ext/crypto/lib.rs b/ext/crypto/lib.rs
index c96029bf4a..69dcd1413a 100644
--- a/ext/crypto/lib.rs
+++ b/ext/crypto/lib.rs
@@ -6,10 +6,7 @@ use aes_kw::KekAes256;
 
 use base64::prelude::BASE64_URL_SAFE_NO_PAD;
 use base64::Engine;
-use deno_core::error::custom_error;
 use deno_core::error::not_supported;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 
@@ -17,7 +14,6 @@ use deno_core::unsync::spawn_blocking;
 use deno_core::JsBuffer;
 use deno_core::OpState;
 use serde::Deserialize;
-use shared::operation_error;
 
 use p256::elliptic_curve::sec1::FromEncodedPoint;
 use p256::pkcs8::DecodePrivateKey;
@@ -67,15 +63,24 @@ mod x25519;
 mod x448;
 
 pub use crate::decrypt::op_crypto_decrypt;
+pub use crate::decrypt::DecryptError;
+pub use crate::ed25519::Ed25519Error;
 pub use crate::encrypt::op_crypto_encrypt;
+pub use crate::encrypt::EncryptError;
 pub use crate::export_key::op_crypto_export_key;
+pub use crate::export_key::ExportKeyError;
 pub use crate::generate_key::op_crypto_generate_key;
+pub use crate::generate_key::GenerateKeyError;
 pub use crate::import_key::op_crypto_import_key;
+pub use crate::import_key::ImportKeyError;
 use crate::key::Algorithm;
 use crate::key::CryptoHash;
 use crate::key::CryptoNamedCurve;
 use crate::key::HkdfOutput;
+pub use crate::shared::SharedError;
 use crate::shared::V8RawKeyData;
+pub use crate::x25519::X25519Error;
+pub use crate::x448::X448Error;
 
 deno_core::extension!(deno_crypto,
   deps = [ deno_webidl, deno_web ],
@@ -127,11 +132,63 @@ deno_core::extension!(deno_crypto,
   },
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum Error {
+  #[error(transparent)]
+  General(#[from] SharedError),
+  #[error(transparent)]
+  JoinError(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Der(#[from] rsa::pkcs1::der::Error),
+  #[error("Missing argument hash")]
+  MissingArgumentHash,
+  #[error("Missing argument saltLength")]
+  MissingArgumentSaltLength,
+  #[error("unsupported algorithm")]
+  UnsupportedAlgorithm,
+  #[error(transparent)]
+  KeyRejected(#[from] ring::error::KeyRejected),
+  #[error(transparent)]
+  RSA(#[from] rsa::Error),
+  #[error(transparent)]
+  Pkcs1(#[from] rsa::pkcs1::Error),
+  #[error(transparent)]
+  Unspecified(#[from] ring::error::Unspecified),
+  #[error("Invalid key format")]
+  InvalidKeyFormat,
+  #[error(transparent)]
+  P256Ecdsa(#[from] p256::ecdsa::Error),
+  #[error("Unexpected error decoding private key")]
+  DecodePrivateKey,
+  #[error("Missing argument publicKey")]
+  MissingArgumentPublicKey,
+  #[error("Missing argument namedCurve")]
+  MissingArgumentNamedCurve,
+  #[error("Missing argument info")]
+  MissingArgumentInfo,
+  #[error("The length provided for HKDF is too large")]
+  HKDFLengthTooLarge,
+  #[error(transparent)]
+  Base64Decode(#[from] base64::DecodeError),
+  #[error("Data must be multiple of 8 bytes")]
+  DataInvalidSize,
+  #[error("Invalid key length")]
+  InvalidKeyLength,
+  #[error("encryption error")]
+  EncryptionError,
+  #[error("decryption error - integrity check failed")]
+  DecryptionError,
+  #[error("The ArrayBufferView's byte length ({0}) exceeds the number of bytes of entropy available via this API (65536)")]
+  ArrayBufferViewLengthExceeded(usize),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[op2]
 #[serde]
 pub fn op_crypto_base64url_decode(
   #[string] data: String,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   let data: Vec<u8> = BASE64_URL_SAFE_NO_PAD.decode(data)?;
   Ok(data.into())
 }
@@ -147,12 +204,9 @@ pub fn op_crypto_base64url_encode(#[buffer] data: JsBuffer) -> String {
 pub fn op_crypto_get_random_values(
   state: &mut OpState,
   #[buffer] out: &mut [u8],
-) -> Result<(), AnyError> {
+) -> Result<(), Error> {
   if out.len() > 65536 {
-    return Err(
-      deno_web::DomExceptionQuotaExceededError::new(&format!("The ArrayBufferView's byte length ({}) exceeds the number of bytes of entropy available via this API (65536)", out.len()))
-        .into(),
-    );
+    return Err(Error::ArrayBufferViewLengthExceeded(out.len()));
   }
 
   let maybe_seeded_rng = state.try_borrow_mut::<StdRng>();
@@ -204,7 +258,7 @@ pub struct SignArg {
 pub async fn op_crypto_sign_key(
   #[serde] args: SignArg,
   #[buffer] zero_copy: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   deno_core::unsync::spawn_blocking(move || {
     let data = &*zero_copy;
     let algorithm = args.algorithm;
@@ -213,10 +267,7 @@ pub async fn op_crypto_sign_key(
       Algorithm::RsassaPkcs1v15 => {
         use rsa::pkcs1v15::SigningKey;
         let private_key = RsaPrivateKey::from_pkcs1_der(&args.key.data)?;
-        match args
-          .hash
-          .ok_or_else(|| type_error("Missing argument hash".to_string()))?
-        {
+        match args.hash.ok_or_else(|| Error::MissingArgumentHash)? {
           CryptoHash::Sha1 => {
             let signing_key = SigningKey::<Sha1>::new(private_key);
             signing_key.sign(data)
@@ -239,15 +290,13 @@ pub async fn op_crypto_sign_key(
       Algorithm::RsaPss => {
         let private_key = RsaPrivateKey::from_pkcs1_der(&args.key.data)?;
 
-        let salt_len = args.salt_length.ok_or_else(|| {
-          type_error("Missing argument saltLength".to_string())
-        })? as usize;
+        let salt_len = args
+          .salt_length
+          .ok_or_else(|| Error::MissingArgumentSaltLength)?
+          as usize;
 
         let mut rng = OsRng;
-        match args
-          .hash
-          .ok_or_else(|| type_error("Missing argument hash".to_string()))?
-        {
+        match args.hash.ok_or_else(|| Error::MissingArgumentHash)? {
           CryptoHash::Sha1 => {
             let signing_key = Pss::new_with_salt::<Sha1>(salt_len);
             let hashed = Sha1::digest(data);
@@ -272,8 +321,10 @@ pub async fn op_crypto_sign_key(
         .to_vec()
       }
       Algorithm::Ecdsa => {
-        let curve: &EcdsaSigningAlgorithm =
-          args.named_curve.ok_or_else(not_supported)?.into();
+        let curve: &EcdsaSigningAlgorithm = args
+          .named_curve
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
 
         let rng = RingRand::SystemRandom::new();
         let key_pair = EcdsaKeyPair::from_pkcs8(curve, &args.key.data, &rng)?;
@@ -282,7 +333,7 @@ pub async fn op_crypto_sign_key(
         if let Some(hash) = args.hash {
           match hash {
             CryptoHash::Sha256 | CryptoHash::Sha384 => (),
-            _ => return Err(type_error("Unsupported algorithm")),
+            _ => return Err(Error::UnsupportedAlgorithm),
           }
         };
 
@@ -292,14 +343,17 @@ pub async fn op_crypto_sign_key(
         signature.as_ref().to_vec()
       }
       Algorithm::Hmac => {
-        let hash: HmacAlgorithm = args.hash.ok_or_else(not_supported)?.into();
+        let hash: HmacAlgorithm = args
+          .hash
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
 
         let key = HmacKey::new(hash, &args.key.data);
 
         let signature = ring::hmac::sign(&key, data);
         signature.as_ref().to_vec()
       }
-      _ => return Err(type_error("Unsupported algorithm".to_string())),
+      _ => return Err(Error::UnsupportedAlgorithm),
     };
 
     Ok(signature.into())
@@ -322,7 +376,7 @@ pub struct VerifyArg {
 pub async fn op_crypto_verify_key(
   #[serde] args: VerifyArg,
   #[buffer] zero_copy: JsBuffer,
-) -> Result<bool, AnyError> {
+) -> Result<bool, Error> {
   deno_core::unsync::spawn_blocking(move || {
     let data = &*zero_copy;
     let algorithm = args.algorithm;
@@ -333,10 +387,7 @@ pub async fn op_crypto_verify_key(
         use rsa::pkcs1v15::VerifyingKey;
         let public_key = read_rsa_public_key(args.key)?;
         let signature: Signature = args.signature.as_ref().try_into()?;
-        match args
-          .hash
-          .ok_or_else(|| type_error("Missing argument hash".to_string()))?
-        {
+        match args.hash.ok_or_else(|| Error::MissingArgumentHash)? {
           CryptoHash::Sha1 => {
             let verifying_key = VerifyingKey::<Sha1>::new(public_key);
             verifying_key.verify(data, &signature).is_ok()
@@ -359,14 +410,12 @@ pub async fn op_crypto_verify_key(
         let public_key = read_rsa_public_key(args.key)?;
         let signature = args.signature.as_ref();
 
-        let salt_len = args.salt_length.ok_or_else(|| {
-          type_error("Missing argument saltLength".to_string())
-        })? as usize;
+        let salt_len = args
+          .salt_length
+          .ok_or_else(|| Error::MissingArgumentSaltLength)?
+          as usize;
 
-        match args
-          .hash
-          .ok_or_else(|| type_error("Missing argument hash".to_string()))?
-        {
+        match args.hash.ok_or_else(|| Error::MissingArgumentHash)? {
           CryptoHash::Sha1 => {
             let pss = Pss::new_with_salt::<Sha1>(salt_len);
             let hashed = Sha1::digest(data);
@@ -390,15 +439,22 @@ pub async fn op_crypto_verify_key(
         }
       }
       Algorithm::Hmac => {
-        let hash: HmacAlgorithm = args.hash.ok_or_else(not_supported)?.into();
+        let hash: HmacAlgorithm = args
+          .hash
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
         let key = HmacKey::new(hash, &args.key.data);
         ring::hmac::verify(&key, data, &args.signature).is_ok()
       }
       Algorithm::Ecdsa => {
-        let signing_alg: &EcdsaSigningAlgorithm =
-          args.named_curve.ok_or_else(not_supported)?.into();
-        let verify_alg: &EcdsaVerificationAlgorithm =
-          args.named_curve.ok_or_else(not_supported)?.into();
+        let signing_alg: &EcdsaSigningAlgorithm = args
+          .named_curve
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
+        let verify_alg: &EcdsaVerificationAlgorithm = args
+          .named_curve
+          .ok_or_else(|| Error::Other(not_supported()))?
+          .into();
 
         let private_key;
 
@@ -411,7 +467,7 @@ pub async fn op_crypto_verify_key(
             private_key.public_key().as_ref()
           }
           KeyType::Public => &*args.key.data,
-          _ => return Err(type_error("Invalid Key format".to_string())),
+          _ => return Err(Error::InvalidKeyFormat),
         };
 
         let public_key =
@@ -419,7 +475,7 @@ pub async fn op_crypto_verify_key(
 
         public_key.verify(data, &args.signature).is_ok()
       }
-      _ => return Err(type_error("Unsupported algorithm".to_string())),
+      _ => return Err(Error::UnsupportedAlgorithm),
     };
 
     Ok(verification)
@@ -447,70 +503,68 @@ pub struct DeriveKeyArg {
 pub async fn op_crypto_derive_bits(
   #[serde] args: DeriveKeyArg,
   #[buffer] zero_copy: Option<JsBuffer>,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   deno_core::unsync::spawn_blocking(move || {
     let algorithm = args.algorithm;
     match algorithm {
       Algorithm::Pbkdf2 => {
-        let zero_copy = zero_copy.ok_or_else(not_supported)?;
+        let zero_copy =
+          zero_copy.ok_or_else(|| Error::Other(not_supported()))?;
         let salt = &*zero_copy;
         // The caller must validate these cases.
         assert!(args.length > 0);
         assert!(args.length % 8 == 0);
 
-        let algorithm = match args.hash.ok_or_else(not_supported)? {
-          CryptoHash::Sha1 => pbkdf2::PBKDF2_HMAC_SHA1,
-          CryptoHash::Sha256 => pbkdf2::PBKDF2_HMAC_SHA256,
-          CryptoHash::Sha384 => pbkdf2::PBKDF2_HMAC_SHA384,
-          CryptoHash::Sha512 => pbkdf2::PBKDF2_HMAC_SHA512,
-        };
+        let algorithm =
+          match args.hash.ok_or_else(|| Error::Other(not_supported()))? {
+            CryptoHash::Sha1 => pbkdf2::PBKDF2_HMAC_SHA1,
+            CryptoHash::Sha256 => pbkdf2::PBKDF2_HMAC_SHA256,
+            CryptoHash::Sha384 => pbkdf2::PBKDF2_HMAC_SHA384,
+            CryptoHash::Sha512 => pbkdf2::PBKDF2_HMAC_SHA512,
+          };
 
         // This will never panic. We have already checked length earlier.
-        let iterations =
-          NonZeroU32::new(args.iterations.ok_or_else(not_supported)?).unwrap();
+        let iterations = NonZeroU32::new(
+          args
+            .iterations
+            .ok_or_else(|| Error::Other(not_supported()))?,
+        )
+        .unwrap();
         let secret = args.key.data;
         let mut out = vec![0; args.length / 8];
         pbkdf2::derive(algorithm, iterations, salt, &secret, &mut out);
         Ok(out.into())
       }
       Algorithm::Ecdh => {
-        let named_curve = args.named_curve.ok_or_else(|| {
-          type_error("Missing argument namedCurve".to_string())
-        })?;
+        let named_curve = args
+          .named_curve
+          .ok_or_else(|| Error::MissingArgumentNamedCurve)?;
 
         let public_key = args
           .public_key
-          .ok_or_else(|| type_error("Missing argument publicKey"))?;
+          .ok_or_else(|| Error::MissingArgumentPublicKey)?;
 
         match named_curve {
           CryptoNamedCurve::P256 => {
             let secret_key = p256::SecretKey::from_pkcs8_der(&args.key.data)
-              .map_err(|_| {
-                type_error("Unexpected error decoding private key")
-              })?;
+              .map_err(|_| Error::DecodePrivateKey)?;
 
             let public_key = match public_key.r#type {
               KeyType::Private => {
                 p256::SecretKey::from_pkcs8_der(&public_key.data)
-                  .map_err(|_| {
-                    type_error("Unexpected error decoding private key")
-                  })?
+                  .map_err(|_| Error::DecodePrivateKey)?
                   .public_key()
               }
               KeyType::Public => {
                 let point = p256::EncodedPoint::from_bytes(public_key.data)
-                  .map_err(|_| {
-                    type_error("Unexpected error decoding private key")
-                  })?;
+                  .map_err(|_| Error::DecodePrivateKey)?;
 
                 let pk = p256::PublicKey::from_encoded_point(&point);
                 // pk is a constant time Option.
                 if pk.is_some().into() {
                   pk.unwrap()
                 } else {
-                  return Err(type_error(
-                    "Unexpected error decoding private key",
-                  ));
+                  return Err(Error::DecodePrivateKey);
                 }
               }
               _ => unreachable!(),
@@ -526,32 +580,24 @@ pub async fn op_crypto_derive_bits(
           }
           CryptoNamedCurve::P384 => {
             let secret_key = p384::SecretKey::from_pkcs8_der(&args.key.data)
-              .map_err(|_| {
-                type_error("Unexpected error decoding private key")
-              })?;
+              .map_err(|_| Error::DecodePrivateKey)?;
 
             let public_key = match public_key.r#type {
               KeyType::Private => {
                 p384::SecretKey::from_pkcs8_der(&public_key.data)
-                  .map_err(|_| {
-                    type_error("Unexpected error decoding private key")
-                  })?
+                  .map_err(|_| Error::DecodePrivateKey)?
                   .public_key()
               }
               KeyType::Public => {
                 let point = p384::EncodedPoint::from_bytes(public_key.data)
-                  .map_err(|_| {
-                    type_error("Unexpected error decoding private key")
-                  })?;
+                  .map_err(|_| Error::DecodePrivateKey)?;
 
                 let pk = p384::PublicKey::from_encoded_point(&point);
                 // pk is a constant time Option.
                 if pk.is_some().into() {
                   pk.unwrap()
                 } else {
-                  return Err(type_error(
-                    "Unexpected error decoding private key",
-                  ));
+                  return Err(Error::DecodePrivateKey);
                 }
               }
               _ => unreachable!(),
@@ -568,18 +614,18 @@ pub async fn op_crypto_derive_bits(
         }
       }
       Algorithm::Hkdf => {
-        let zero_copy = zero_copy.ok_or_else(not_supported)?;
+        let zero_copy =
+          zero_copy.ok_or_else(|| Error::Other(not_supported()))?;
         let salt = &*zero_copy;
-        let algorithm = match args.hash.ok_or_else(not_supported)? {
-          CryptoHash::Sha1 => hkdf::HKDF_SHA1_FOR_LEGACY_USE_ONLY,
-          CryptoHash::Sha256 => hkdf::HKDF_SHA256,
-          CryptoHash::Sha384 => hkdf::HKDF_SHA384,
-          CryptoHash::Sha512 => hkdf::HKDF_SHA512,
-        };
+        let algorithm =
+          match args.hash.ok_or_else(|| Error::Other(not_supported()))? {
+            CryptoHash::Sha1 => hkdf::HKDF_SHA1_FOR_LEGACY_USE_ONLY,
+            CryptoHash::Sha256 => hkdf::HKDF_SHA256,
+            CryptoHash::Sha384 => hkdf::HKDF_SHA384,
+            CryptoHash::Sha512 => hkdf::HKDF_SHA512,
+          };
 
-        let info = args
-          .info
-          .ok_or_else(|| type_error("Missing argument info".to_string()))?;
+        let info = args.info.ok_or_else(|| Error::MissingArgumentInfo)?;
         // IKM
         let secret = args.key.data;
         // L
@@ -588,23 +634,20 @@ pub async fn op_crypto_derive_bits(
         let salt = hkdf::Salt::new(algorithm, salt);
         let prk = salt.extract(&secret);
         let info = &[&*info];
-        let okm = prk.expand(info, HkdfOutput(length)).map_err(|_e| {
-          custom_error(
-            "DOMExceptionOperationError",
-            "The length provided for HKDF is too large",
-          )
-        })?;
+        let okm = prk
+          .expand(info, HkdfOutput(length))
+          .map_err(|_e| Error::HKDFLengthTooLarge)?;
         let mut r = vec![0u8; length];
         okm.fill(&mut r)?;
         Ok(r.into())
       }
-      _ => Err(type_error("Unsupported algorithm".to_string())),
+      _ => Err(Error::UnsupportedAlgorithm),
     }
   })
   .await?
 }
 
-fn read_rsa_public_key(key_data: KeyData) -> Result<RsaPublicKey, AnyError> {
+fn read_rsa_public_key(key_data: KeyData) -> Result<RsaPublicKey, Error> {
   let public_key = match key_data.r#type {
     KeyType::Private => {
       RsaPrivateKey::from_pkcs1_der(&key_data.data)?.to_public_key()
@@ -617,7 +660,7 @@ fn read_rsa_public_key(key_data: KeyData) -> Result<RsaPublicKey, AnyError> {
 
 #[op2]
 #[string]
-pub fn op_crypto_random_uuid(state: &mut OpState) -> Result<String, AnyError> {
+pub fn op_crypto_random_uuid(state: &mut OpState) -> Result<String, Error> {
   let maybe_seeded_rng = state.try_borrow_mut::<StdRng>();
   let uuid = if let Some(seeded_rng) = maybe_seeded_rng {
     let mut bytes = [0u8; 16];
@@ -638,7 +681,7 @@ pub fn op_crypto_random_uuid(state: &mut OpState) -> Result<String, AnyError> {
 pub async fn op_crypto_subtle_digest(
   #[serde] algorithm: CryptoHash,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   let output = spawn_blocking(move || {
     digest::digest(algorithm.into(), &data)
       .as_ref()
@@ -662,7 +705,7 @@ pub struct WrapUnwrapKeyArg {
 pub fn op_crypto_wrap_key(
   #[serde] args: WrapUnwrapKeyArg,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   let algorithm = args.algorithm;
 
   match algorithm {
@@ -670,20 +713,20 @@ pub fn op_crypto_wrap_key(
       let key = args.key.as_secret_key()?;
 
       if data.len() % 8 != 0 {
-        return Err(type_error("Data must be multiple of 8 bytes"));
+        return Err(Error::DataInvalidSize);
       }
 
       let wrapped_key = match key.len() {
         16 => KekAes128::new(key.into()).wrap_vec(&data),
         24 => KekAes192::new(key.into()).wrap_vec(&data),
         32 => KekAes256::new(key.into()).wrap_vec(&data),
-        _ => return Err(type_error("Invalid key length")),
+        _ => return Err(Error::InvalidKeyLength),
       }
-      .map_err(|_| operation_error("encryption error"))?;
+      .map_err(|_| Error::EncryptionError)?;
 
       Ok(wrapped_key.into())
     }
-    _ => Err(type_error("Unsupported algorithm")),
+    _ => Err(Error::UnsupportedAlgorithm),
   }
 }
 
@@ -692,29 +735,27 @@ pub fn op_crypto_wrap_key(
 pub fn op_crypto_unwrap_key(
   #[serde] args: WrapUnwrapKeyArg,
   #[buffer] data: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, Error> {
   let algorithm = args.algorithm;
   match algorithm {
     Algorithm::AesKw => {
       let key = args.key.as_secret_key()?;
 
       if data.len() % 8 != 0 {
-        return Err(type_error("Data must be multiple of 8 bytes"));
+        return Err(Error::DataInvalidSize);
       }
 
       let unwrapped_key = match key.len() {
         16 => KekAes128::new(key.into()).unwrap_vec(&data),
         24 => KekAes192::new(key.into()).unwrap_vec(&data),
         32 => KekAes256::new(key.into()).unwrap_vec(&data),
-        _ => return Err(type_error("Invalid key length")),
+        _ => return Err(Error::InvalidKeyLength),
       }
-      .map_err(|_| {
-        operation_error("decryption error - integrity check failed")
-      })?;
+      .map_err(|_| Error::DecryptionError)?;
 
       Ok(unwrapped_key.into())
     }
-    _ => Err(type_error("Unsupported algorithm")),
+    _ => Err(Error::UnsupportedAlgorithm),
   }
 }
 
diff --git a/ext/crypto/shared.rs b/ext/crypto/shared.rs
index d06a268cd6..f70d32856c 100644
--- a/ext/crypto/shared.rs
+++ b/ext/crypto/shared.rs
@@ -2,9 +2,6 @@
 
 use std::borrow::Cow;
 
-use deno_core::error::custom_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::JsBuffer;
 use deno_core::ToJsBuffer;
 use elliptic_curve::sec1::ToEncodedPoint;
@@ -63,47 +60,73 @@ pub enum RustRawKeyData {
   Public(ToJsBuffer),
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum SharedError {
+  #[error("expected valid private key")]
+  ExpectedValidPrivateKey,
+  #[error("expected valid public key")]
+  ExpectedValidPublicKey,
+  #[error("expected valid private EC key")]
+  ExpectedValidPrivateECKey,
+  #[error("expected valid public EC key")]
+  ExpectedValidPublicECKey,
+  #[error("expected private key")]
+  ExpectedPrivateKey,
+  #[error("expected public key")]
+  ExpectedPublicKey,
+  #[error("expected secret key")]
+  ExpectedSecretKey,
+  #[error("failed to decode private key")]
+  FailedDecodePrivateKey,
+  #[error("failed to decode public key")]
+  FailedDecodePublicKey,
+  #[error("unsupported format")]
+  UnsupportedFormat,
+}
+
 impl V8RawKeyData {
-  pub fn as_rsa_public_key(&self) -> Result<Cow<'_, [u8]>, AnyError> {
+  pub fn as_rsa_public_key(&self) -> Result<Cow<'_, [u8]>, SharedError> {
     match self {
       V8RawKeyData::Public(data) => Ok(Cow::Borrowed(data)),
       V8RawKeyData::Private(data) => {
         let private_key = RsaPrivateKey::from_pkcs1_der(data)
-          .map_err(|_| type_error("expected valid private key"))?;
+          .map_err(|_| SharedError::ExpectedValidPrivateKey)?;
 
         let public_key_doc = private_key
           .to_public_key()
           .to_pkcs1_der()
-          .map_err(|_| type_error("expected valid public key"))?;
+          .map_err(|_| SharedError::ExpectedValidPublicKey)?;
 
         Ok(Cow::Owned(public_key_doc.as_bytes().into()))
       }
-      _ => Err(type_error("expected public key")),
+      _ => Err(SharedError::ExpectedPublicKey),
     }
   }
 
-  pub fn as_rsa_private_key(&self) -> Result<&[u8], AnyError> {
+  pub fn as_rsa_private_key(&self) -> Result<&[u8], SharedError> {
     match self {
       V8RawKeyData::Private(data) => Ok(data),
-      _ => Err(type_error("expected private key")),
+      _ => Err(SharedError::ExpectedPrivateKey),
     }
   }
 
-  pub fn as_secret_key(&self) -> Result<&[u8], AnyError> {
+  pub fn as_secret_key(&self) -> Result<&[u8], SharedError> {
     match self {
       V8RawKeyData::Secret(data) => Ok(data),
-      _ => Err(type_error("expected secret key")),
+      _ => Err(SharedError::ExpectedSecretKey),
     }
   }
 
-  pub fn as_ec_public_key_p256(&self) -> Result<p256::EncodedPoint, AnyError> {
+  pub fn as_ec_public_key_p256(
+    &self,
+  ) -> Result<p256::EncodedPoint, SharedError> {
     match self {
       V8RawKeyData::Public(data) => p256::PublicKey::from_sec1_bytes(data)
         .map(|p| p.to_encoded_point(false))
-        .map_err(|_| type_error("expected valid public EC key")),
+        .map_err(|_| SharedError::ExpectedValidPublicECKey),
       V8RawKeyData::Private(data) => {
         let signing_key = p256::SecretKey::from_pkcs8_der(data)
-          .map_err(|_| type_error("expected valid private EC key"))?;
+          .map_err(|_| SharedError::ExpectedValidPrivateECKey)?;
         Ok(signing_key.public_key().to_encoded_point(false))
       }
       // Should never reach here.
@@ -111,14 +134,16 @@ impl V8RawKeyData {
     }
   }
 
-  pub fn as_ec_public_key_p384(&self) -> Result<p384::EncodedPoint, AnyError> {
+  pub fn as_ec_public_key_p384(
+    &self,
+  ) -> Result<p384::EncodedPoint, SharedError> {
     match self {
       V8RawKeyData::Public(data) => p384::PublicKey::from_sec1_bytes(data)
         .map(|p| p.to_encoded_point(false))
-        .map_err(|_| type_error("expected valid public EC key")),
+        .map_err(|_| SharedError::ExpectedValidPublicECKey),
       V8RawKeyData::Private(data) => {
         let signing_key = p384::SecretKey::from_pkcs8_der(data)
-          .map_err(|_| type_error("expected valid private EC key"))?;
+          .map_err(|_| SharedError::ExpectedValidPrivateECKey)?;
         Ok(signing_key.public_key().to_encoded_point(false))
       }
       // Should never reach here.
@@ -126,16 +151,18 @@ impl V8RawKeyData {
     }
   }
 
-  pub fn as_ec_public_key_p521(&self) -> Result<p521::EncodedPoint, AnyError> {
+  pub fn as_ec_public_key_p521(
+    &self,
+  ) -> Result<p521::EncodedPoint, SharedError> {
     match self {
       V8RawKeyData::Public(data) => {
         // public_key is a serialized EncodedPoint
         p521::EncodedPoint::from_bytes(data)
-          .map_err(|_| type_error("expected valid public EC key"))
+          .map_err(|_| SharedError::ExpectedValidPublicECKey)
       }
       V8RawKeyData::Private(data) => {
         let signing_key = p521::SecretKey::from_pkcs8_der(data)
-          .map_err(|_| type_error("expected valid private EC key"))?;
+          .map_err(|_| SharedError::ExpectedValidPrivateECKey)?;
         Ok(signing_key.public_key().to_encoded_point(false))
       }
       // Should never reach here.
@@ -143,26 +170,10 @@ impl V8RawKeyData {
     }
   }
 
-  pub fn as_ec_private_key(&self) -> Result<&[u8], AnyError> {
+  pub fn as_ec_private_key(&self) -> Result<&[u8], SharedError> {
     match self {
       V8RawKeyData::Private(data) => Ok(data),
-      _ => Err(type_error("expected private key")),
+      _ => Err(SharedError::ExpectedPrivateKey),
     }
   }
 }
-
-pub fn data_error(msg: impl Into<Cow<'static, str>>) -> AnyError {
-  custom_error("DOMExceptionDataError", msg)
-}
-
-pub fn not_supported_error(msg: impl Into<Cow<'static, str>>) -> AnyError {
-  custom_error("DOMExceptionNotSupportedError", msg)
-}
-
-pub fn operation_error(msg: impl Into<Cow<'static, str>>) -> AnyError {
-  custom_error("DOMExceptionOperationError", msg)
-}
-
-pub fn unsupported_format() -> AnyError {
-  not_supported_error("unsupported format")
-}
diff --git a/ext/crypto/x25519.rs b/ext/crypto/x25519.rs
index cdbd1d7c8f..d2c4d986b9 100644
--- a/ext/crypto/x25519.rs
+++ b/ext/crypto/x25519.rs
@@ -1,8 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use curve25519_dalek::montgomery::MontgomeryPoint;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 use elliptic_curve::pkcs8::PrivateKeyInfo;
@@ -13,6 +11,14 @@ use spki::der::asn1::BitString;
 use spki::der::Decode;
 use spki::der::Encode;
 
+#[derive(Debug, thiserror::Error)]
+pub enum X25519Error {
+  #[error("Failed to export key")]
+  FailedExport,
+  #[error(transparent)]
+  Der(#[from] spki::der::Error),
+}
+
 #[op2(fast)]
 pub fn op_crypto_generate_x25519_keypair(
   #[buffer] pkey: &mut [u8],
@@ -113,7 +119,7 @@ pub fn op_crypto_import_pkcs8_x25519(
 #[serde]
 pub fn op_crypto_export_spki_x25519(
   #[buffer] pubkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, X25519Error> {
   let key_info = spki::SubjectPublicKeyInfo {
     algorithm: spki::AlgorithmIdentifierRef {
       // id-X25519
@@ -125,9 +131,7 @@ pub fn op_crypto_export_spki_x25519(
   Ok(
     key_info
       .to_der()
-      .map_err(|_| {
-        custom_error("DOMExceptionOperationError", "Failed to export key")
-      })?
+      .map_err(|_| X25519Error::FailedExport)?
       .into(),
   )
 }
@@ -136,7 +140,7 @@ pub fn op_crypto_export_spki_x25519(
 #[serde]
 pub fn op_crypto_export_pkcs8_x25519(
   #[buffer] pkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, X25519Error> {
   use rsa::pkcs1::der::Encode;
 
   // This should probably use OneAsymmetricKey instead
diff --git a/ext/crypto/x448.rs b/ext/crypto/x448.rs
index 3c8f24c319..89bf48e28b 100644
--- a/ext/crypto/x448.rs
+++ b/ext/crypto/x448.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
+
 use deno_core::op2;
 use deno_core::ToJsBuffer;
 use ed448_goldilocks::curve::MontgomeryPoint;
@@ -13,6 +12,14 @@ use spki::der::asn1::BitString;
 use spki::der::Decode;
 use spki::der::Encode;
 
+#[derive(Debug, thiserror::Error)]
+pub enum X448Error {
+  #[error("Failed to export key")]
+  FailedExport,
+  #[error(transparent)]
+  Der(#[from] spki::der::Error),
+}
+
 #[op2(fast)]
 pub fn op_crypto_generate_x448_keypair(
   #[buffer] pkey: &mut [u8],
@@ -56,7 +63,7 @@ const X448_OID: const_oid::ObjectIdentifier =
 #[serde]
 pub fn op_crypto_export_spki_x448(
   #[buffer] pubkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, X448Error> {
   let key_info = spki::SubjectPublicKeyInfo {
     algorithm: spki::AlgorithmIdentifierRef {
       oid: X448_OID,
@@ -67,9 +74,7 @@ pub fn op_crypto_export_spki_x448(
   Ok(
     key_info
       .to_der()
-      .map_err(|_| {
-        custom_error("DOMExceptionOperationError", "Failed to export key")
-      })?
+      .map_err(|_| X448Error::FailedExport)?
       .into(),
   )
 }
@@ -78,7 +83,7 @@ pub fn op_crypto_export_spki_x448(
 #[serde]
 pub fn op_crypto_export_pkcs8_x448(
   #[buffer] pkey: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, X448Error> {
   use rsa::pkcs1::der::Encode;
 
   let pk_info = rsa::pkcs8::PrivateKeyInfo {
diff --git a/ext/fetch/23_response.js b/ext/fetch/23_response.js
index ff4ad5facd..278dcb7dec 100644
--- a/ext/fetch/23_response.js
+++ b/ext/fetch/23_response.js
@@ -61,6 +61,15 @@ const _mimeType = Symbol("mime type");
 const _body = Symbol("body");
 const _brand = webidl.brand;
 
+// it's slightly faster to cache these
+const webidlConvertersBodyInitDomString =
+  webidl.converters["BodyInit_DOMString?"];
+const webidlConvertersUSVString = webidl.converters["USVString"];
+const webidlConvertersUnsignedShort = webidl.converters["unsigned short"];
+const webidlConvertersAny = webidl.converters["any"];
+const webidlConvertersByteString = webidl.converters["ByteString"];
+const webidlConvertersHeadersInit = webidl.converters["HeadersInit"];
+
 /**
  * @typedef InnerResponse
  * @property {"basic" | "cors" | "default" | "error" | "opaque" | "opaqueredirect"} type
@@ -259,8 +268,8 @@ class Response {
    */
   static redirect(url, status = 302) {
     const prefix = "Failed to execute 'Response.redirect'";
-    url = webidl.converters["USVString"](url, prefix, "Argument 1");
-    status = webidl.converters["unsigned short"](status, prefix, "Argument 2");
+    url = webidlConvertersUSVString(url, prefix, "Argument 1");
+    status = webidlConvertersUnsignedShort(status, prefix, "Argument 2");
 
     const baseURL = getLocationHref();
     const parsedURL = new URL(url, baseURL);
@@ -286,8 +295,8 @@ class Response {
    */
   static json(data = undefined, init = { __proto__: null }) {
     const prefix = "Failed to execute 'Response.json'";
-    data = webidl.converters.any(data);
-    init = webidl.converters["ResponseInit_fast"](init, prefix, "Argument 2");
+    data = webidlConvertersAny(data);
+    init = webidlConvertersResponseInitFast(init, prefix, "Argument 2");
 
     const str = serializeJSValueToJSONString(data);
     const res = extractBody(str);
@@ -313,8 +322,8 @@ class Response {
     }
 
     const prefix = "Failed to construct 'Response'";
-    body = webidl.converters["BodyInit_DOMString?"](body, prefix, "Argument 1");
-    init = webidl.converters["ResponseInit_fast"](init, prefix, "Argument 2");
+    body = webidlConvertersBodyInitDomString(body, prefix, "Argument 1");
+    init = webidlConvertersResponseInitFast(init, prefix, "Argument 2");
 
     this[_response] = newInnerResponse();
     this[_headers] = headersFromHeaderList(
@@ -443,47 +452,49 @@ webidl.converters["Response"] = webidl.createInterfaceConverter(
   "Response",
   ResponsePrototype,
 );
-webidl.converters["ResponseInit"] = webidl.createDictionaryConverter(
-  "ResponseInit",
-  [{
-    key: "status",
-    defaultValue: 200,
-    converter: webidl.converters["unsigned short"],
-  }, {
-    key: "statusText",
-    defaultValue: "",
-    converter: webidl.converters["ByteString"],
-  }, {
-    key: "headers",
-    converter: webidl.converters["HeadersInit"],
-  }],
-);
-webidl.converters["ResponseInit_fast"] = function (
-  init,
-  prefix,
-  context,
-  opts,
-) {
-  if (init === undefined || init === null) {
-    return { status: 200, statusText: "", headers: undefined };
-  }
-  // Fast path, if not a proxy
-  if (typeof init === "object" && !core.isProxy(init)) {
-    // Not a proxy fast path
-    const status = init.status !== undefined
-      ? webidl.converters["unsigned short"](init.status)
-      : 200;
-    const statusText = init.statusText !== undefined
-      ? webidl.converters["ByteString"](init.statusText)
-      : "";
-    const headers = init.headers !== undefined
-      ? webidl.converters["HeadersInit"](init.headers)
-      : undefined;
-    return { status, statusText, headers };
-  }
-  // Slow default path
-  return webidl.converters["ResponseInit"](init, prefix, context, opts);
-};
+const webidlConvertersResponseInit = webidl.converters["ResponseInit"] = webidl
+  .createDictionaryConverter(
+    "ResponseInit",
+    [{
+      key: "status",
+      defaultValue: 200,
+      converter: webidlConvertersUnsignedShort,
+    }, {
+      key: "statusText",
+      defaultValue: "",
+      converter: webidlConvertersByteString,
+    }, {
+      key: "headers",
+      converter: webidlConvertersHeadersInit,
+    }],
+  );
+const webidlConvertersResponseInitFast = webidl
+  .converters["ResponseInit_fast"] = function (
+    init,
+    prefix,
+    context,
+    opts,
+  ) {
+    if (init === undefined || init === null) {
+      return { status: 200, statusText: "", headers: undefined };
+    }
+    // Fast path, if not a proxy
+    if (typeof init === "object" && !core.isProxy(init)) {
+      // Not a proxy fast path
+      const status = init.status !== undefined
+        ? webidlConvertersUnsignedShort(init.status)
+        : 200;
+      const statusText = init.statusText !== undefined
+        ? webidlConvertersByteString(init.statusText)
+        : "";
+      const headers = init.headers !== undefined
+        ? webidlConvertersHeadersInit(init.headers)
+        : undefined;
+      return { status, statusText, headers };
+    }
+    // Slow default path
+    return webidlConvertersResponseInit(init, prefix, context, opts);
+  };
 
 /**
  * @param {Response} response
diff --git a/ext/fetch/Cargo.toml b/ext/fetch/Cargo.toml
index cc9e4f03d3..93fc88ae64 100644
--- a/ext/fetch/Cargo.toml
+++ b/ext/fetch/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_fetch"
-version = "0.195.0"
+version = "0.199.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -32,6 +32,7 @@ percent-encoding.workspace = true
 rustls-webpki.workspace = true
 serde.workspace = true
 serde_json.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
 tokio-rustls.workspace = true
 tokio-socks.workspace = true
diff --git a/ext/fetch/fs_fetch_handler.rs b/ext/fetch/fs_fetch_handler.rs
index 4c2b81f356..c236dd9c67 100644
--- a/ext/fetch/fs_fetch_handler.rs
+++ b/ext/fetch/fs_fetch_handler.rs
@@ -4,7 +4,6 @@ use crate::CancelHandle;
 use crate::CancelableResponseFuture;
 use crate::FetchHandler;
 
-use deno_core::error::type_error;
 use deno_core::futures::FutureExt;
 use deno_core::futures::TryFutureExt;
 use deno_core::futures::TryStreamExt;
@@ -42,9 +41,7 @@ impl FetchHandler for FsFetchHandler {
         .map_err(|_| ())?;
       Ok::<_, ()>(response)
     }
-    .map_err(move |_| {
-      type_error("NetworkError when attempting to fetch resource")
-    })
+    .map_err(move |_| super::FetchError::NetworkError)
     .or_cancel(&cancel_handle)
     .boxed_local();
 
diff --git a/ext/fetch/lib.rs b/ext/fetch/lib.rs
index 88f3038528..4df8dc3d72 100644
--- a/ext/fetch/lib.rs
+++ b/ext/fetch/lib.rs
@@ -17,10 +17,6 @@ use std::sync::Arc;
 use std::task::Context;
 use std::task::Poll;
 
-use deno_core::anyhow::anyhow;
-use deno_core::anyhow::Error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::stream::Peekable;
 use deno_core::futures::Future;
 use deno_core::futures::FutureExt;
@@ -28,6 +24,7 @@ use deno_core::futures::Stream;
 use deno_core::futures::StreamExt;
 use deno_core::futures::TryFutureExt;
 use deno_core::op2;
+use deno_core::url;
 use deno_core::url::Url;
 use deno_core::AsyncRefCell;
 use deno_core::AsyncResult;
@@ -87,15 +84,18 @@ pub struct Options {
   pub root_cert_store_provider: Option<Arc<dyn RootCertStoreProvider>>,
   pub proxy: Option<Proxy>,
   #[allow(clippy::type_complexity)]
-  pub request_builder_hook:
-    Option<fn(&mut http::Request<ReqBody>) -> Result<(), AnyError>>,
+  pub request_builder_hook: Option<
+    fn(&mut http::Request<ReqBody>) -> Result<(), deno_core::error::AnyError>,
+  >,
   pub unsafely_ignore_certificate_errors: Option<Vec<String>>,
   pub client_cert_chain_and_key: TlsKeys,
   pub file_fetch_handler: Rc<dyn FetchHandler>,
 }
 
 impl Options {
-  pub fn root_cert_store(&self) -> Result<Option<RootCertStore>, AnyError> {
+  pub fn root_cert_store(
+    &self,
+  ) -> Result<Option<RootCertStore>, deno_core::error::AnyError> {
     Ok(match &self.root_cert_store_provider {
       Some(provider) => Some(provider.get_or_try_init()?.clone()),
       None => None,
@@ -144,6 +144,51 @@ deno_core::extension!(deno_fetch,
   },
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum FetchError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error("NetworkError when attempting to fetch resource")]
+  NetworkError,
+  #[error("Fetching files only supports the GET method: received {0}")]
+  FsNotGet(Method),
+  #[error("Invalid URL {0}")]
+  InvalidUrl(Url),
+  #[error(transparent)]
+  InvalidHeaderName(#[from] http::header::InvalidHeaderName),
+  #[error(transparent)]
+  InvalidHeaderValue(#[from] http::header::InvalidHeaderValue),
+  #[error("{0:?}")]
+  DataUrl(data_url::DataUrlError),
+  #[error("{0:?}")]
+  Base64(data_url::forgiving_base64::InvalidBase64),
+  #[error("Blob for the given URL not found.")]
+  BlobNotFound,
+  #[error("Url scheme '{0}' not supported")]
+  SchemeNotSupported(String),
+  #[error("Request was cancelled")]
+  RequestCanceled,
+  #[error(transparent)]
+  Http(#[from] http::Error),
+  #[error(transparent)]
+  ClientCreate(#[from] HttpClientCreateError),
+  #[error(transparent)]
+  Url(#[from] url::ParseError),
+  #[error(transparent)]
+  Method(#[from] http::method::InvalidMethod),
+  #[error(transparent)]
+  ClientSend(#[from] ClientSendError),
+  #[error(transparent)]
+  RequestBuilderHook(deno_core::error::AnyError),
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  // Only used for node upgrade
+  #[error(transparent)]
+  Hyper(#[from] hyper::Error),
+}
+
 pub type CancelableResponseFuture =
   Pin<Box<dyn Future<Output = CancelableResponseResult>>>;
 
@@ -170,11 +215,7 @@ impl FetchHandler for DefaultFileFetchHandler {
     _state: &mut OpState,
     _url: &Url,
   ) -> (CancelableResponseFuture, Option<Rc<CancelHandle>>) {
-    let fut = async move {
-      Ok(Err(type_error(
-        "NetworkError when attempting to fetch resource",
-      )))
-    };
+    let fut = async move { Ok(Err(FetchError::NetworkError)) };
     (Box::pin(fut), None)
   }
 }
@@ -191,7 +232,7 @@ pub struct FetchReturn {
 
 pub fn get_or_create_client_from_state(
   state: &mut OpState,
-) -> Result<Client, AnyError> {
+) -> Result<Client, HttpClientCreateError> {
   if let Some(client) = state.try_borrow::<Client>() {
     Ok(client.clone())
   } else {
@@ -204,11 +245,13 @@ pub fn get_or_create_client_from_state(
 
 pub fn create_client_from_options(
   options: &Options,
-) -> Result<Client, AnyError> {
+) -> Result<Client, HttpClientCreateError> {
   create_http_client(
     &options.user_agent,
     CreateHttpClientOptions {
-      root_cert_store: options.root_cert_store()?,
+      root_cert_store: options
+        .root_cert_store()
+        .map_err(HttpClientCreateError::RootCertStore)?,
       ca_certs: vec![],
       proxy: options.proxy.clone(),
       unsafely_ignore_certificate_errors: options
@@ -230,7 +273,9 @@ pub fn create_client_from_options(
 #[allow(clippy::type_complexity)]
 pub struct ResourceToBodyAdapter(
   Rc<dyn Resource>,
-  Option<Pin<Box<dyn Future<Output = Result<BufView, Error>>>>>,
+  Option<
+    Pin<Box<dyn Future<Output = Result<BufView, deno_core::error::AnyError>>>>,
+  >,
 );
 
 impl ResourceToBodyAdapter {
@@ -246,7 +291,7 @@ unsafe impl Send for ResourceToBodyAdapter {}
 unsafe impl Sync for ResourceToBodyAdapter {}
 
 impl Stream for ResourceToBodyAdapter {
-  type Item = Result<Bytes, Error>;
+  type Item = Result<Bytes, deno_core::error::AnyError>;
 
   fn poll_next(
     self: Pin<&mut Self>,
@@ -276,7 +321,7 @@ impl Stream for ResourceToBodyAdapter {
 
 impl hyper::body::Body for ResourceToBodyAdapter {
   type Data = Bytes;
-  type Error = Error;
+  type Error = deno_core::error::AnyError;
 
   fn poll_frame(
     self: Pin<&mut Self>,
@@ -301,13 +346,13 @@ pub trait FetchPermissions {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), deno_core::error::AnyError>;
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn check_read<'a>(
     &mut self,
     p: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError>;
+  ) -> Result<Cow<'a, Path>, deno_core::error::AnyError>;
 }
 
 impl FetchPermissions for deno_permissions::PermissionsContainer {
@@ -316,7 +361,7 @@ impl FetchPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     url: &Url,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), deno_core::error::AnyError> {
     deno_permissions::PermissionsContainer::check_net_url(self, url, api_name)
   }
 
@@ -325,7 +370,7 @@ impl FetchPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     path: &'a Path,
     api_name: &str,
-  ) -> Result<Cow<'a, Path>, AnyError> {
+  ) -> Result<Cow<'a, Path>, deno_core::error::AnyError> {
     deno_permissions::PermissionsContainer::check_read_path(
       self,
       path,
@@ -346,12 +391,15 @@ pub fn op_fetch<FP>(
   has_body: bool,
   #[buffer] data: Option<JsBuffer>,
   #[smi] resource: Option<ResourceId>,
-) -> Result<FetchReturn, AnyError>
+) -> Result<FetchReturn, FetchError>
 where
   FP: FetchPermissions + 'static,
 {
   let (client, allow_host) = if let Some(rid) = client_rid {
-    let r = state.resource_table.get::<HttpClientResource>(rid)?;
+    let r = state
+      .resource_table
+      .get::<HttpClientResource>(rid)
+      .map_err(FetchError::Resource)?;
     (r.client.clone(), r.allow_host)
   } else {
     (get_or_create_client_from_state(state)?, false)
@@ -364,20 +412,18 @@ where
   let scheme = url.scheme();
   let (request_rid, cancel_handle_rid) = match scheme {
     "file" => {
-      let path = url.to_file_path().map_err(|_| {
-        type_error("NetworkError when attempting to fetch resource")
-      })?;
+      let path = url.to_file_path().map_err(|_| FetchError::NetworkError)?;
       let permissions = state.borrow_mut::<FP>();
-      let path = permissions.check_read(&path, "fetch()")?;
+      let path = permissions
+        .check_read(&path, "fetch()")
+        .map_err(FetchError::Permission)?;
       let url = match path {
         Cow::Owned(path) => Url::from_file_path(path).unwrap(),
         Cow::Borrowed(_) => url,
       };
 
       if method != Method::GET {
-        return Err(type_error(format!(
-          "Fetching files only supports the GET method: received {method}"
-        )));
+        return Err(FetchError::FsNotGet(method));
       }
 
       let Options {
@@ -396,13 +442,15 @@ where
     }
     "http" | "https" => {
       let permissions = state.borrow_mut::<FP>();
-      permissions.check_net_url(&url, "fetch()")?;
+      permissions
+        .check_net_url(&url, "fetch()")
+        .map_err(FetchError::Resource)?;
 
       let maybe_authority = extract_authority(&mut url);
       let uri = url
         .as_str()
         .parse::<Uri>()
-        .map_err(|_| type_error(format!("Invalid URL {url}")))?;
+        .map_err(|_| FetchError::InvalidUrl(url.clone()))?;
 
       let mut con_len = None;
       let body = if has_body {
@@ -416,7 +464,10 @@ where
               .boxed()
           }
           (_, Some(resource)) => {
-            let resource = state.resource_table.take_any(resource)?;
+            let resource = state
+              .resource_table
+              .take_any(resource)
+              .map_err(FetchError::Resource)?;
             match resource.size_hint() {
               (body_size, Some(n)) if body_size == n && body_size > 0 => {
                 con_len = Some(body_size);
@@ -453,10 +504,8 @@ where
       }
 
       for (key, value) in headers {
-        let name = HeaderName::from_bytes(&key)
-          .map_err(|err| type_error(err.to_string()))?;
-        let v = HeaderValue::from_bytes(&value)
-          .map_err(|err| type_error(err.to_string()))?;
+        let name = HeaderName::from_bytes(&key)?;
+        let v = HeaderValue::from_bytes(&value)?;
 
         if (name != HOST || allow_host) && name != CONTENT_LENGTH {
           request.headers_mut().append(name, v);
@@ -474,20 +523,18 @@ where
       let options = state.borrow::<Options>();
       if let Some(request_builder_hook) = options.request_builder_hook {
         request_builder_hook(&mut request)
-          .map_err(|err| type_error(err.to_string()))?;
+          .map_err(FetchError::RequestBuilderHook)?;
       }
 
       let cancel_handle = CancelHandle::new_rc();
       let cancel_handle_ = cancel_handle.clone();
 
-      let fut = {
-        async move {
-          client
-            .send(request)
-            .map_err(Into::into)
-            .or_cancel(cancel_handle_)
-            .await
-        }
+      let fut = async move {
+        client
+          .send(request)
+          .map_err(Into::into)
+          .or_cancel(cancel_handle_)
+          .await
       };
 
       let request_rid = state.resource_table.add(FetchRequestResource {
@@ -501,12 +548,10 @@ where
       (request_rid, Some(cancel_handle_rid))
     }
     "data" => {
-      let data_url = DataUrl::process(url.as_str())
-        .map_err(|e| type_error(format!("{e:?}")))?;
+      let data_url =
+        DataUrl::process(url.as_str()).map_err(FetchError::DataUrl)?;
 
-      let (body, _) = data_url
-        .decode_to_vec()
-        .map_err(|e| type_error(format!("{e:?}")))?;
+      let (body, _) = data_url.decode_to_vec().map_err(FetchError::Base64)?;
       let body = http_body_util::Full::new(body.into())
         .map_err(|never| match never {})
         .boxed();
@@ -528,11 +573,9 @@ where
     "blob" => {
       // Blob URL resolution happens in the JS side of fetch. If we got here is
       // because the URL isn't an object URL.
-      return Err(type_error("Blob for the given URL not found."));
-    }
-    _ => {
-      return Err(type_error(format!("Url scheme '{scheme}' not supported")))
+      return Err(FetchError::BlobNotFound);
     }
+    _ => return Err(FetchError::SchemeNotSupported(scheme.to_string())),
   };
 
   Ok(FetchReturn {
@@ -564,11 +607,12 @@ pub struct FetchResponse {
 pub async fn op_fetch_send(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<FetchResponse, AnyError> {
+) -> Result<FetchResponse, FetchError> {
   let request = state
     .borrow_mut()
     .resource_table
-    .take::<FetchRequestResource>(rid)?;
+    .take::<FetchRequestResource>(rid)
+    .map_err(FetchError::Resource)?;
 
   let request = Rc::try_unwrap(request)
     .ok()
@@ -581,22 +625,23 @@ pub async fn op_fetch_send(
       // If any error in the chain is a hyper body error, return that as a special result we can use to
       // reconstruct an error chain (eg: `new TypeError(..., { cause: new Error(...) })`).
       // TODO(mmastrac): it would be a lot easier if we just passed a v8::Global through here instead
-      let mut err_ref: &dyn std::error::Error = err.as_ref();
-      while let Some(err_src) = std::error::Error::source(err_ref) {
-        if let Some(err_src) = err_src.downcast_ref::<hyper::Error>() {
-          if let Some(err_src) = std::error::Error::source(err_src) {
-            return Ok(FetchResponse {
-              error: Some((err.to_string(), err_src.to_string())),
-              ..Default::default()
-            });
+
+      if let FetchError::ClientSend(err_src) = &err {
+        if let Some(client_err) = std::error::Error::source(&err_src.source) {
+          if let Some(err_src) = client_err.downcast_ref::<hyper::Error>() {
+            if let Some(err_src) = std::error::Error::source(err_src) {
+              return Ok(FetchResponse {
+                error: Some((err.to_string(), err_src.to_string())),
+                ..Default::default()
+              });
+            }
           }
         }
-        err_ref = err_src;
       }
 
-      return Err(type_error(err.to_string()));
+      return Err(err);
     }
-    Err(_) => return Err(type_error("Request was cancelled")),
+    Err(_) => return Err(FetchError::RequestCanceled),
   };
 
   let status = res.status();
@@ -636,7 +681,7 @@ pub async fn op_fetch_send(
 }
 
 type CancelableResponseResult =
-  Result<Result<http::Response<ResBody>, AnyError>, Canceled>;
+  Result<Result<http::Response<ResBody>, FetchError>, Canceled>;
 
 pub struct FetchRequestResource {
   pub future: Pin<Box<dyn Future<Output = CancelableResponseResult>>>,
@@ -691,7 +736,7 @@ impl FetchResponseResource {
     }
   }
 
-  pub async fn upgrade(self) -> Result<hyper::upgrade::Upgraded, AnyError> {
+  pub async fn upgrade(self) -> Result<hyper::upgrade::Upgraded, hyper::Error> {
     let reader = self.response_reader.into_inner();
     match reader {
       FetchResponseReader::Start(resp) => Ok(hyper::upgrade::on(resp).await?),
@@ -746,7 +791,9 @@ impl Resource for FetchResponseResource {
             // safely call `await` on it without creating a race condition.
             Some(_) => match reader.as_mut().next().await.unwrap() {
               Ok(chunk) => assert!(chunk.is_empty()),
-              Err(err) => break Err(type_error(err.to_string())),
+              Err(err) => {
+                break Err(deno_core::error::type_error(err.to_string()))
+              }
             },
             None => break Ok(BufView::empty()),
           }
@@ -809,14 +856,16 @@ pub fn op_fetch_custom_client<FP>(
   state: &mut OpState,
   #[serde] args: CreateHttpClientArgs,
   #[cppgc] tls_keys: &TlsKeysHolder,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, FetchError>
 where
   FP: FetchPermissions + 'static,
 {
   if let Some(proxy) = args.proxy.clone() {
     let permissions = state.borrow_mut::<FP>();
     let url = Url::parse(&proxy.url)?;
-    permissions.check_net_url(&url, "Deno.createHttpClient()")?;
+    permissions
+      .check_net_url(&url, "Deno.createHttpClient()")
+      .map_err(FetchError::Permission)?;
   }
 
   let options = state.borrow::<Options>();
@@ -829,7 +878,9 @@ where
   let client = create_http_client(
     &options.user_agent,
     CreateHttpClientOptions {
-      root_cert_store: options.root_cert_store()?,
+      root_cert_store: options
+        .root_cert_store()
+        .map_err(HttpClientCreateError::RootCertStore)?,
       ca_certs,
       proxy: args.proxy,
       unsafely_ignore_certificate_errors: options
@@ -887,19 +938,34 @@ impl Default for CreateHttpClientOptions {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpClientCreateError {
+  #[error(transparent)]
+  Tls(deno_tls::TlsError),
+  #[error("Illegal characters in User-Agent: received {0}")]
+  InvalidUserAgent(String),
+  #[error("invalid proxy url")]
+  InvalidProxyUrl,
+  #[error("Cannot create Http Client: either `http1` or `http2` needs to be set to true")]
+  HttpVersionSelectionInvalid,
+  #[error(transparent)]
+  RootCertStore(deno_core::error::AnyError),
+}
+
 /// Create new instance of async Client. This client supports
 /// proxies and doesn't follow redirects.
 pub fn create_http_client(
   user_agent: &str,
   options: CreateHttpClientOptions,
-) -> Result<Client, AnyError> {
+) -> Result<Client, HttpClientCreateError> {
   let mut tls_config = deno_tls::create_client_config(
     options.root_cert_store,
     options.ca_certs,
     options.unsafely_ignore_certificate_errors,
     options.client_cert_chain_and_key.into(),
     deno_tls::SocketUse::Http,
-  )?;
+  )
+  .map_err(HttpClientCreateError::Tls)?;
 
   // Proxy TLS should not send ALPN
   tls_config.alpn_protocols.clear();
@@ -919,9 +985,7 @@ pub fn create_http_client(
   http_connector.enforce_http(false);
 
   let user_agent = user_agent.parse::<HeaderValue>().map_err(|_| {
-    type_error(format!(
-      "Illegal characters in User-Agent: received {user_agent}"
-    ))
+    HttpClientCreateError::InvalidUserAgent(user_agent.to_string())
   })?;
 
   let mut builder =
@@ -932,7 +996,7 @@ pub fn create_http_client(
   let mut proxies = proxy::from_env();
   if let Some(proxy) = options.proxy {
     let mut intercept = proxy::Intercept::all(&proxy.url)
-      .ok_or_else(|| type_error("invalid proxy url"))?;
+      .ok_or_else(|| HttpClientCreateError::InvalidProxyUrl)?;
     if let Some(basic_auth) = &proxy.basic_auth {
       intercept.set_auth(&basic_auth.username, &basic_auth.password);
     }
@@ -964,7 +1028,7 @@ pub fn create_http_client(
     }
     (true, true) => {}
     (false, false) => {
-      return Err(type_error("Cannot create Http Client: either `http1` or `http2` needs to be set to true"))
+      return Err(HttpClientCreateError::HttpVersionSelectionInvalid)
     }
   }
 
@@ -980,10 +1044,8 @@ pub fn create_http_client(
 
 #[op2]
 #[serde]
-pub fn op_utf8_to_byte_string(
-  #[string] input: String,
-) -> Result<ByteString, AnyError> {
-  Ok(input.into())
+pub fn op_utf8_to_byte_string(#[string] input: String) -> ByteString {
+  input.into()
 }
 
 #[derive(Clone, Debug)]
@@ -1003,7 +1065,7 @@ const STAR_STAR: HeaderValue = HeaderValue::from_static("*/*");
 #[derive(Debug)]
 pub struct ClientSendError {
   uri: Uri,
-  source: hyper_util::client::legacy::Error,
+  pub source: hyper_util::client::legacy::Error,
 }
 
 impl ClientSendError {
@@ -1075,12 +1137,14 @@ impl Client {
       .oneshot(req)
       .await
       .map_err(|e| ClientSendError { uri, source: e })?;
-    Ok(resp.map(|b| b.map_err(|e| anyhow!(e)).boxed()))
+    Ok(resp.map(|b| b.map_err(|e| deno_core::anyhow::anyhow!(e)).boxed()))
   }
 }
 
-pub type ReqBody = http_body_util::combinators::BoxBody<Bytes, Error>;
-pub type ResBody = http_body_util::combinators::BoxBody<Bytes, Error>;
+pub type ReqBody =
+  http_body_util::combinators::BoxBody<Bytes, deno_core::error::AnyError>;
+pub type ResBody =
+  http_body_util::combinators::BoxBody<Bytes, deno_core::error::AnyError>;
 
 /// Copied from https://github.com/seanmonstar/reqwest/blob/b9d62a0323d96f11672a61a17bf8849baec00275/src/async_impl/request.rs#L572
 /// Check the request URL for a "username:password" type authority, and if
diff --git a/ext/ffi/Cargo.toml b/ext/ffi/Cargo.toml
index 23a2aee1cd..58144790bf 100644
--- a/ext/ffi/Cargo.toml
+++ b/ext/ffi/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_ffi"
-version = "0.158.0"
+version = "0.162.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -21,9 +21,12 @@ dynasmrt = "1.2.3"
 libffi = "=3.2.0"
 libffi-sys = "=2.3.0"
 log.workspace = true
+num-bigint.workspace = true
 serde.workspace = true
 serde-value = "0.7"
 serde_json = "1.0"
+thiserror.workspace = true
+tokio.workspace = true
 
 [target.'cfg(windows)'.dependencies]
 winapi = { workspace = true, features = ["errhandlingapi", "minwindef", "ntdef", "winbase", "winnt"] }
diff --git a/ext/ffi/call.rs b/ext/ffi/call.rs
index 3572b9e813..ef61dc383e 100644
--- a/ext/ffi/call.rs
+++ b/ext/ffi/call.rs
@@ -7,23 +7,36 @@ use crate::symbol::NativeType;
 use crate::symbol::Symbol;
 use crate::FfiPermissions;
 use crate::ForeignFunction;
-use deno_core::anyhow::anyhow;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde_json::Value;
+use deno_core::serde_v8::BigInt as V8BigInt;
 use deno_core::serde_v8::ExternalPointer;
 use deno_core::unsync::spawn_blocking;
 use deno_core::v8;
 use deno_core::OpState;
 use deno_core::ResourceId;
 use libffi::middle::Arg;
+use num_bigint::BigInt;
 use serde::Serialize;
 use std::cell::RefCell;
 use std::ffi::c_void;
 use std::future::Future;
 use std::rc::Rc;
 
+#[derive(Debug, thiserror::Error)]
+pub enum CallError {
+  #[error(transparent)]
+  IR(#[from] IRError),
+  #[error("Nonblocking FFI call failed: {0}")]
+  NonblockingCallFailure(#[source] tokio::task::JoinError),
+  #[error("Invalid FFI symbol name: '{0}'")]
+  InvalidSymbol(String),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  Callback(#[from] super::CallbackError),
+}
+
 // SAFETY: Makes an FFI call
 unsafe fn ffi_call_rtype_struct(
   cif: &libffi::middle::Cif,
@@ -45,7 +58,7 @@ pub(crate) fn ffi_call_sync<'scope>(
   args: v8::FunctionCallbackArguments,
   symbol: &Symbol,
   out_buffer: Option<OutBuffer>,
-) -> Result<NativeValue, AnyError>
+) -> Result<NativeValue, CallError>
 where
   'scope: 'scope,
 {
@@ -191,6 +204,7 @@ where
 #[serde(untagged)]
 pub enum FfiValue {
   Value(Value),
+  BigInt(V8BigInt),
   External(ExternalPointer),
 }
 
@@ -201,7 +215,7 @@ fn ffi_call(
   parameter_types: &[NativeType],
   result_type: NativeType,
   out_buffer: Option<OutBuffer>,
-) -> Result<FfiValue, AnyError> {
+) -> FfiValue {
   let call_args: Vec<Arg> = call_args
     .iter()
     .enumerate()
@@ -214,7 +228,7 @@ fn ffi_call(
   // SAFETY: types in the `Cif` match the actual calling convention and
   // types of symbol.
   unsafe {
-    Ok(match result_type {
+    match result_type {
       NativeType::Void => {
         cif.call::<()>(fun_ptr, &call_args);
         FfiValue::Value(Value::from(()))
@@ -240,18 +254,18 @@ fn ffi_call(
       NativeType::I32 => {
         FfiValue::Value(Value::from(cif.call::<i32>(fun_ptr, &call_args)))
       }
-      NativeType::U64 => {
-        FfiValue::Value(Value::from(cif.call::<u64>(fun_ptr, &call_args)))
-      }
-      NativeType::I64 => {
-        FfiValue::Value(Value::from(cif.call::<i64>(fun_ptr, &call_args)))
-      }
-      NativeType::USize => {
-        FfiValue::Value(Value::from(cif.call::<usize>(fun_ptr, &call_args)))
-      }
-      NativeType::ISize => {
-        FfiValue::Value(Value::from(cif.call::<isize>(fun_ptr, &call_args)))
-      }
+      NativeType::U64 => FfiValue::BigInt(V8BigInt::from(BigInt::from(
+        cif.call::<u64>(fun_ptr, &call_args),
+      ))),
+      NativeType::I64 => FfiValue::BigInt(V8BigInt::from(BigInt::from(
+        cif.call::<i64>(fun_ptr, &call_args),
+      ))),
+      NativeType::USize => FfiValue::BigInt(V8BigInt::from(BigInt::from(
+        cif.call::<usize>(fun_ptr, &call_args),
+      ))),
+      NativeType::ISize => FfiValue::BigInt(V8BigInt::from(BigInt::from(
+        cif.call::<isize>(fun_ptr, &call_args),
+      ))),
       NativeType::F32 => {
         FfiValue::Value(Value::from(cif.call::<f32>(fun_ptr, &call_args)))
       }
@@ -267,7 +281,7 @@ fn ffi_call(
         ffi_call_rtype_struct(cif, &fun_ptr, call_args, out_buffer.unwrap().0);
         FfiValue::Value(Value::Null)
       }
-    })
+    }
   }
 }
 
@@ -280,14 +294,16 @@ pub fn op_ffi_call_ptr_nonblocking<FP>(
   #[serde] def: ForeignFunction,
   parameters: v8::Local<v8::Array>,
   out_buffer: Option<v8::Local<v8::TypedArray>>,
-) -> Result<impl Future<Output = Result<FfiValue, AnyError>>, AnyError>
+) -> Result<impl Future<Output = Result<FfiValue, CallError>>, CallError>
 where
   FP: FfiPermissions + 'static,
 {
   {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<FP>();
-    permissions.check_partial_no_path()?;
+    permissions
+      .check_partial_no_path()
+      .map_err(CallError::Permission)?;
   };
 
   let symbol = PtrSymbol::new(pointer, &def)?;
@@ -309,7 +325,7 @@ where
   Ok(async move {
     let result = join_handle
       .await
-      .map_err(|err| anyhow!("Nonblocking FFI call failed: {}", err))??;
+      .map_err(CallError::NonblockingCallFailure)?;
     // SAFETY: Same return type declared to libffi; trust user to have it right beyond that.
     Ok(result)
   })
@@ -325,16 +341,17 @@ pub fn op_ffi_call_nonblocking(
   #[string] symbol: String,
   parameters: v8::Local<v8::Array>,
   out_buffer: Option<v8::Local<v8::TypedArray>>,
-) -> Result<impl Future<Output = Result<FfiValue, AnyError>>, AnyError> {
+) -> Result<impl Future<Output = Result<FfiValue, CallError>>, CallError> {
   let symbol = {
     let state = state.borrow();
-    let resource = state.resource_table.get::<DynamicLibraryResource>(rid)?;
+    let resource = state
+      .resource_table
+      .get::<DynamicLibraryResource>(rid)
+      .map_err(CallError::Permission)?;
     let symbols = &resource.symbols;
     *symbols
       .get(&symbol)
-      .ok_or_else(|| {
-        type_error(format!("Invalid FFI symbol name: '{symbol}'"))
-      })?
+      .ok_or_else(|| CallError::InvalidSymbol(symbol))?
       .clone()
   };
 
@@ -362,7 +379,7 @@ pub fn op_ffi_call_nonblocking(
   Ok(async move {
     let result = join_handle
       .await
-      .map_err(|err| anyhow!("Nonblocking FFI call failed: {}", err))??;
+      .map_err(CallError::NonblockingCallFailure)?;
     // SAFETY: Same return type declared to libffi; trust user to have it right beyond that.
     Ok(result)
   })
@@ -377,14 +394,16 @@ pub fn op_ffi_call_ptr<FP>(
   #[serde] def: ForeignFunction,
   parameters: v8::Local<v8::Array>,
   out_buffer: Option<v8::Local<v8::TypedArray>>,
-) -> Result<FfiValue, AnyError>
+) -> Result<FfiValue, CallError>
 where
   FP: FfiPermissions + 'static,
 {
   {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<FP>();
-    permissions.check_partial_no_path()?;
+    permissions
+      .check_partial_no_path()
+      .map_err(CallError::Permission)?;
   };
 
   let symbol = PtrSymbol::new(pointer, &def)?;
@@ -399,7 +418,7 @@ where
     &def.parameters,
     def.result.clone(),
     out_buffer_ptr,
-  )?;
+  );
   // SAFETY: Same return type declared to libffi; trust user to have it right beyond that.
   Ok(result)
 }
diff --git a/ext/ffi/callback.rs b/ext/ffi/callback.rs
index 6fa166f52b..f33e0413a3 100644
--- a/ext/ffi/callback.rs
+++ b/ext/ffi/callback.rs
@@ -3,7 +3,6 @@
 use crate::symbol::NativeType;
 use crate::FfiPermissions;
 use crate::ForeignFunction;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::v8::TryCatch;
@@ -34,6 +33,16 @@ thread_local! {
   static LOCAL_THREAD_ID: RefCell<u32> = const { RefCell::new(0) };
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum CallbackError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[derive(Clone)]
 pub struct PtrSymbol {
   pub cif: libffi::middle::Cif,
@@ -44,7 +53,7 @@ impl PtrSymbol {
   pub fn new(
     fn_ptr: *mut c_void,
     def: &ForeignFunction,
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, CallbackError> {
     let ptr = libffi::middle::CodePtr::from_ptr(fn_ptr as _);
     let cif = libffi::middle::Cif::new(
       def
@@ -52,8 +61,13 @@ impl PtrSymbol {
         .clone()
         .into_iter()
         .map(libffi::middle::Type::try_from)
-        .collect::<Result<Vec<_>, _>>()?,
-      def.result.clone().try_into()?,
+        .collect::<Result<Vec<_>, _>>()
+        .map_err(CallbackError::Other)?,
+      def
+        .result
+        .clone()
+        .try_into()
+        .map_err(CallbackError::Other)?,
     );
 
     Ok(Self { cif, ptr })
@@ -522,10 +536,12 @@ unsafe fn do_ffi_callback(
 pub fn op_ffi_unsafe_callback_ref(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<impl Future<Output = Result<(), AnyError>>, AnyError> {
+) -> Result<impl Future<Output = ()>, CallbackError> {
   let state = state.borrow();
-  let callback_resource =
-    state.resource_table.get::<UnsafeCallbackResource>(rid)?;
+  let callback_resource = state
+    .resource_table
+    .get::<UnsafeCallbackResource>(rid)
+    .map_err(CallbackError::Resource)?;
 
   Ok(async move {
     let info: &mut CallbackInfo =
@@ -536,7 +552,6 @@ pub fn op_ffi_unsafe_callback_ref(
       .into_future()
       .or_cancel(callback_resource.cancel.clone())
       .await;
-    Ok(())
   })
 }
 
@@ -552,12 +567,14 @@ pub fn op_ffi_unsafe_callback_create<FP, 'scope>(
   scope: &mut v8::HandleScope<'scope>,
   #[serde] args: RegisterCallbackArgs,
   cb: v8::Local<v8::Function>,
-) -> Result<v8::Local<'scope, v8::Value>, AnyError>
+) -> Result<v8::Local<'scope, v8::Value>, CallbackError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(CallbackError::Permission)?;
 
   let thread_id: u32 = LOCAL_THREAD_ID.with(|s| {
     let value = *s.borrow();
@@ -593,8 +610,10 @@ where
       .parameters
       .into_iter()
       .map(libffi::middle::Type::try_from)
-      .collect::<Result<Vec<_>, _>>()?,
-    libffi::middle::Type::try_from(args.result)?,
+      .collect::<Result<Vec<_>, _>>()
+      .map_err(CallbackError::Other)?,
+    libffi::middle::Type::try_from(args.result)
+      .map_err(CallbackError::Other)?,
   );
 
   // SAFETY: CallbackInfo is leaked, is not null and stays valid as long as the callback exists.
@@ -624,14 +643,16 @@ pub fn op_ffi_unsafe_callback_close(
   state: &mut OpState,
   scope: &mut v8::HandleScope,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), CallbackError> {
   // SAFETY: This drops the closure and the callback info associated with it.
   // Any retained function pointers to the closure become dangling pointers.
   // It is up to the user to know that it is safe to call the `close()` on the
   // UnsafeCallback instance.
   unsafe {
-    let callback_resource =
-      state.resource_table.take::<UnsafeCallbackResource>(rid)?;
+    let callback_resource = state
+      .resource_table
+      .take::<UnsafeCallbackResource>(rid)
+      .map_err(CallbackError::Resource)?;
     let info = Box::from_raw(callback_resource.info);
     let _ = v8::Global::from_raw(scope, info.callback);
     let _ = v8::Global::from_raw(scope, info.context);
diff --git a/ext/ffi/dlfcn.rs b/ext/ffi/dlfcn.rs
index 10199bf858..53bdcbc5cc 100644
--- a/ext/ffi/dlfcn.rs
+++ b/ext/ffi/dlfcn.rs
@@ -6,8 +6,6 @@ use crate::symbol::Symbol;
 use crate::turbocall;
 use crate::turbocall::Turbocall;
 use crate::FfiPermissions;
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::GarbageCollected;
@@ -21,6 +19,22 @@ use std::collections::HashMap;
 use std::ffi::c_void;
 use std::rc::Rc;
 
+#[derive(Debug, thiserror::Error)]
+pub enum DlfcnError {
+  #[error("Failed to register symbol {symbol}: {error}")]
+  RegisterSymbol {
+    symbol: String,
+    #[source]
+    error: dlopen2::Error,
+  },
+  #[error(transparent)]
+  Dlopen(#[from] dlopen2::Error),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 pub struct DynamicLibraryResource {
   lib: Library,
   pub symbols: HashMap<String, Box<Symbol>>,
@@ -37,7 +51,7 @@ impl Resource for DynamicLibraryResource {
 }
 
 impl DynamicLibraryResource {
-  pub fn get_static(&self, symbol: String) -> Result<*mut c_void, AnyError> {
+  pub fn get_static(&self, symbol: String) -> Result<*mut c_void, DlfcnError> {
     // By default, Err returned by this function does not tell
     // which symbol wasn't exported. So we'll modify the error
     // message to include the name of symbol.
@@ -45,9 +59,7 @@ impl DynamicLibraryResource {
     // SAFETY: The obtained T symbol is the size of a pointer.
     match unsafe { self.lib.symbol::<*mut c_void>(&symbol) } {
       Ok(value) => Ok(Ok(value)),
-      Err(err) => Err(generic_error(format!(
-        "Failed to register symbol {symbol}: {err}"
-      ))),
+      Err(error) => Err(DlfcnError::RegisterSymbol { symbol, error }),
     }?
   }
 }
@@ -116,12 +128,14 @@ pub fn op_ffi_load<'scope, FP>(
   scope: &mut v8::HandleScope<'scope>,
   state: &mut OpState,
   #[serde] args: FfiLoadArgs,
-) -> Result<v8::Local<'scope, v8::Value>, AnyError>
+) -> Result<v8::Local<'scope, v8::Value>, DlfcnError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  let path = permissions.check_partial_with_path(&args.path)?;
+  let path = permissions
+    .check_partial_with_path(&args.path)
+    .map_err(DlfcnError::Permission)?;
 
   let lib = Library::open(&path).map_err(|e| {
     dlopen2::Error::OpeningLibraryError(std::io::Error::new(
@@ -152,15 +166,16 @@ where
           // SAFETY: The obtained T symbol is the size of a pointer.
           match unsafe { resource.lib.symbol::<*const c_void>(symbol) } {
             Ok(value) => Ok(value),
-            Err(err) => if foreign_fn.optional {
+            Err(error) => if foreign_fn.optional {
               let null: v8::Local<v8::Value> = v8::null(scope).into();
               let func_key = v8::String::new(scope, &symbol_key).unwrap();
               obj.set(scope, func_key.into(), null);
               break 'register_symbol;
             } else {
-              Err(generic_error(format!(
-                "Failed to register symbol {symbol}: {err}"
-              )))
+              Err(DlfcnError::RegisterSymbol {
+                symbol: symbol.to_owned(),
+                error,
+              })
             },
           }?;
 
@@ -171,8 +186,13 @@ where
             .clone()
             .into_iter()
             .map(libffi::middle::Type::try_from)
-            .collect::<Result<Vec<_>, _>>()?,
-          foreign_fn.result.clone().try_into()?,
+            .collect::<Result<Vec<_>, _>>()
+            .map_err(DlfcnError::Other)?,
+          foreign_fn
+            .result
+            .clone()
+            .try_into()
+            .map_err(DlfcnError::Other)?,
         );
 
         let func_key = v8::String::new(scope, &symbol_key).unwrap();
diff --git a/ext/ffi/ir.rs b/ext/ffi/ir.rs
index ebf64945b4..2e80842166 100644
--- a/ext/ffi/ir.rs
+++ b/ext/ffi/ir.rs
@@ -1,13 +1,55 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use crate::symbol::NativeType;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::v8;
 use libffi::middle::Arg;
 use std::ffi::c_void;
 use std::ptr;
 
+#[derive(Debug, thiserror::Error)]
+pub enum IRError {
+  #[error("Invalid FFI u8 type, expected boolean")]
+  InvalidU8ExpectedBoolean,
+  #[error("Invalid FFI u8 type, expected unsigned integer")]
+  InvalidU8ExpectedUnsignedInteger,
+  #[error("Invalid FFI i8 type, expected integer")]
+  InvalidI8,
+  #[error("Invalid FFI u16 type, expected unsigned integer")]
+  InvalidU16,
+  #[error("Invalid FFI i16 type, expected integer")]
+  InvalidI16,
+  #[error("Invalid FFI u32 type, expected unsigned integer")]
+  InvalidU32,
+  #[error("Invalid FFI i32 type, expected integer")]
+  InvalidI32,
+  #[error("Invalid FFI u64 type, expected unsigned integer")]
+  InvalidU64,
+  #[error("Invalid FFI i64 type, expected integer")]
+  InvalidI64,
+  #[error("Invalid FFI usize type, expected unsigned integer")]
+  InvalidUsize,
+  #[error("Invalid FFI isize type, expected integer")]
+  InvalidIsize,
+  #[error("Invalid FFI f32 type, expected number")]
+  InvalidF32,
+  #[error("Invalid FFI f64 type, expected number")]
+  InvalidF64,
+  #[error("Invalid FFI pointer type, expected null, or External")]
+  InvalidPointerType,
+  #[error(
+    "Invalid FFI buffer type, expected null, ArrayBuffer, or ArrayBufferView"
+  )]
+  InvalidBufferType,
+  #[error("Invalid FFI ArrayBufferView, expected data in the buffer")]
+  InvalidArrayBufferView,
+  #[error("Invalid FFI ArrayBuffer, expected data in buffer")]
+  InvalidArrayBuffer,
+  #[error("Invalid FFI struct type, expected ArrayBuffer, or ArrayBufferView")]
+  InvalidStructType,
+  #[error("Invalid FFI function type, expected null, or External")]
+  InvalidFunctionType,
+}
+
 pub struct OutBuffer(pub *mut u8);
 
 // SAFETY: OutBuffer is allocated by us in 00_ffi.js and is guaranteed to be
@@ -126,9 +168,9 @@ unsafe impl Send for NativeValue {}
 #[inline]
 pub fn ffi_parse_bool_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let bool_value = v8::Local::<v8::Boolean>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI u8 type, expected boolean"))?
+    .map_err(|_| IRError::InvalidU8ExpectedBoolean)?
     .is_true();
   Ok(NativeValue { bool_value })
 }
@@ -136,9 +178,9 @@ pub fn ffi_parse_bool_arg(
 #[inline]
 pub fn ffi_parse_u8_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let u8_value = v8::Local::<v8::Uint32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI u8 type, expected unsigned integer"))?
+    .map_err(|_| IRError::InvalidU8ExpectedUnsignedInteger)?
     .value() as u8;
   Ok(NativeValue { u8_value })
 }
@@ -146,9 +188,9 @@ pub fn ffi_parse_u8_arg(
 #[inline]
 pub fn ffi_parse_i8_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let i8_value = v8::Local::<v8::Int32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI i8 type, expected integer"))?
+    .map_err(|_| IRError::InvalidI8)?
     .value() as i8;
   Ok(NativeValue { i8_value })
 }
@@ -156,9 +198,9 @@ pub fn ffi_parse_i8_arg(
 #[inline]
 pub fn ffi_parse_u16_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let u16_value = v8::Local::<v8::Uint32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI u16 type, expected unsigned integer"))?
+    .map_err(|_| IRError::InvalidU16)?
     .value() as u16;
   Ok(NativeValue { u16_value })
 }
@@ -166,9 +208,9 @@ pub fn ffi_parse_u16_arg(
 #[inline]
 pub fn ffi_parse_i16_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let i16_value = v8::Local::<v8::Int32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI i16 type, expected integer"))?
+    .map_err(|_| IRError::InvalidI16)?
     .value() as i16;
   Ok(NativeValue { i16_value })
 }
@@ -176,9 +218,9 @@ pub fn ffi_parse_i16_arg(
 #[inline]
 pub fn ffi_parse_u32_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let u32_value = v8::Local::<v8::Uint32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI u32 type, expected unsigned integer"))?
+    .map_err(|_| IRError::InvalidU32)?
     .value();
   Ok(NativeValue { u32_value })
 }
@@ -186,9 +228,9 @@ pub fn ffi_parse_u32_arg(
 #[inline]
 pub fn ffi_parse_i32_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let i32_value = v8::Local::<v8::Int32>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI i32 type, expected integer"))?
+    .map_err(|_| IRError::InvalidI32)?
     .value();
   Ok(NativeValue { i32_value })
 }
@@ -197,7 +239,7 @@ pub fn ffi_parse_i32_arg(
 pub fn ffi_parse_u64_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. BigInt: Uncommon and not supported by Fast API, so optimise slow call for this case.
   // 2. Number: Common, supported by Fast API, so let that be the optimal case.
@@ -207,9 +249,7 @@ pub fn ffi_parse_u64_arg(
   } else if let Ok(value) = v8::Local::<v8::Number>::try_from(arg) {
     value.integer_value(scope).unwrap() as u64
   } else {
-    return Err(type_error(
-      "Invalid FFI u64 type, expected unsigned integer",
-    ));
+    return Err(IRError::InvalidU64);
   };
   Ok(NativeValue { u64_value })
 }
@@ -218,7 +258,7 @@ pub fn ffi_parse_u64_arg(
 pub fn ffi_parse_i64_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. BigInt: Uncommon and not supported by Fast API, so optimise slow call for this case.
   // 2. Number: Common, supported by Fast API, so let that be the optimal case.
@@ -228,7 +268,7 @@ pub fn ffi_parse_i64_arg(
   } else if let Ok(value) = v8::Local::<v8::Number>::try_from(arg) {
     value.integer_value(scope).unwrap()
   } else {
-    return Err(type_error("Invalid FFI i64 type, expected integer"));
+    return Err(IRError::InvalidI64);
   };
   Ok(NativeValue { i64_value })
 }
@@ -237,7 +277,7 @@ pub fn ffi_parse_i64_arg(
 pub fn ffi_parse_usize_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. BigInt: Uncommon and not supported by Fast API, so optimise slow call for this case.
   // 2. Number: Common, supported by Fast API, so let that be the optimal case.
@@ -247,7 +287,7 @@ pub fn ffi_parse_usize_arg(
     } else if let Ok(value) = v8::Local::<v8::Number>::try_from(arg) {
       value.integer_value(scope).unwrap() as usize
     } else {
-      return Err(type_error("Invalid FFI usize type, expected integer"));
+      return Err(IRError::InvalidUsize);
     };
   Ok(NativeValue { usize_value })
 }
@@ -256,7 +296,7 @@ pub fn ffi_parse_usize_arg(
 pub fn ffi_parse_isize_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. BigInt: Uncommon and not supported by Fast API, so optimise slow call for this case.
   // 2. Number: Common, supported by Fast API, so let that be the optimal case.
@@ -266,7 +306,7 @@ pub fn ffi_parse_isize_arg(
     } else if let Ok(value) = v8::Local::<v8::Number>::try_from(arg) {
       value.integer_value(scope).unwrap() as isize
     } else {
-      return Err(type_error("Invalid FFI isize type, expected integer"));
+      return Err(IRError::InvalidIsize);
     };
   Ok(NativeValue { isize_value })
 }
@@ -274,9 +314,9 @@ pub fn ffi_parse_isize_arg(
 #[inline]
 pub fn ffi_parse_f32_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let f32_value = v8::Local::<v8::Number>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI f32 type, expected number"))?
+    .map_err(|_| IRError::InvalidF32)?
     .value() as f32;
   Ok(NativeValue { f32_value })
 }
@@ -284,9 +324,9 @@ pub fn ffi_parse_f32_arg(
 #[inline]
 pub fn ffi_parse_f64_arg(
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let f64_value = v8::Local::<v8::Number>::try_from(arg)
-    .map_err(|_| type_error("Invalid FFI f64 type, expected number"))?
+    .map_err(|_| IRError::InvalidF64)?
     .value();
   Ok(NativeValue { f64_value })
 }
@@ -295,15 +335,13 @@ pub fn ffi_parse_f64_arg(
 pub fn ffi_parse_pointer_arg(
   _scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let pointer = if let Ok(value) = v8::Local::<v8::External>::try_from(arg) {
     value.value()
   } else if arg.is_null() {
     ptr::null_mut()
   } else {
-    return Err(type_error(
-      "Invalid FFI pointer type, expected null, or External",
-    ));
+    return Err(IRError::InvalidPointerType);
   };
   Ok(NativeValue { pointer })
 }
@@ -312,7 +350,7 @@ pub fn ffi_parse_pointer_arg(
 pub fn ffi_parse_buffer_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. ArrayBuffer: Fairly common and not supported by Fast API, optimise this case.
   // 2. ArrayBufferView: Common and supported by Fast API
@@ -328,9 +366,7 @@ pub fn ffi_parse_buffer_arg(
     let byte_offset = value.byte_offset();
     let pointer = value
       .buffer(scope)
-      .ok_or_else(|| {
-        type_error("Invalid FFI ArrayBufferView, expected data in the buffer")
-      })?
+      .ok_or(IRError::InvalidArrayBufferView)?
       .data();
     if let Some(non_null) = pointer {
       // SAFETY: Pointer is non-null, and V8 guarantees that the byte_offset
@@ -342,9 +378,7 @@ pub fn ffi_parse_buffer_arg(
   } else if arg.is_null() {
     ptr::null_mut()
   } else {
-    return Err(type_error(
-      "Invalid FFI buffer type, expected null, ArrayBuffer, or ArrayBufferView",
-    ));
+    return Err(IRError::InvalidBufferType);
   };
   Ok(NativeValue { pointer })
 }
@@ -353,7 +387,7 @@ pub fn ffi_parse_buffer_arg(
 pub fn ffi_parse_struct_arg(
   scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   // Order of checking:
   // 1. ArrayBuffer: Fairly common and not supported by Fast API, optimise this case.
   // 2. ArrayBufferView: Common and supported by Fast API
@@ -362,31 +396,23 @@ pub fn ffi_parse_struct_arg(
     if let Some(non_null) = value.data() {
       non_null.as_ptr()
     } else {
-      return Err(type_error(
-        "Invalid FFI ArrayBuffer, expected data in buffer",
-      ));
+      return Err(IRError::InvalidArrayBuffer);
     }
   } else if let Ok(value) = v8::Local::<v8::ArrayBufferView>::try_from(arg) {
     let byte_offset = value.byte_offset();
     let pointer = value
       .buffer(scope)
-      .ok_or_else(|| {
-        type_error("Invalid FFI ArrayBufferView, expected data in the buffer")
-      })?
+      .ok_or(IRError::InvalidArrayBufferView)?
       .data();
     if let Some(non_null) = pointer {
       // SAFETY: Pointer is non-null, and V8 guarantees that the byte_offset
       // is within the buffer backing store.
       unsafe { non_null.as_ptr().add(byte_offset) }
     } else {
-      return Err(type_error(
-        "Invalid FFI ArrayBufferView, expected data in buffer",
-      ));
+      return Err(IRError::InvalidArrayBufferView);
     }
   } else {
-    return Err(type_error(
-      "Invalid FFI struct type, expected ArrayBuffer, or ArrayBufferView",
-    ));
+    return Err(IRError::InvalidStructType);
   };
   Ok(NativeValue { pointer })
 }
@@ -395,15 +421,13 @@ pub fn ffi_parse_struct_arg(
 pub fn ffi_parse_function_arg(
   _scope: &mut v8::HandleScope,
   arg: v8::Local<v8::Value>,
-) -> Result<NativeValue, AnyError> {
+) -> Result<NativeValue, IRError> {
   let pointer = if let Ok(value) = v8::Local::<v8::External>::try_from(arg) {
     value.value()
   } else if arg.is_null() {
     ptr::null_mut()
   } else {
-    return Err(type_error(
-      "Invalid FFI function type, expected null, or External",
-    ));
+    return Err(IRError::InvalidFunctionType);
   };
   Ok(NativeValue { pointer })
 }
@@ -412,7 +436,7 @@ pub fn ffi_parse_args<'scope>(
   scope: &mut v8::HandleScope<'scope>,
   args: v8::Local<v8::Array>,
   parameter_types: &[NativeType],
-) -> Result<Vec<NativeValue>, AnyError>
+) -> Result<Vec<NativeValue>, IRError>
 where
   'scope: 'scope,
 {
diff --git a/ext/ffi/lib.rs b/ext/ffi/lib.rs
index 77ec3c85e3..237f8c3b05 100644
--- a/ext/ffi/lib.rs
+++ b/ext/ffi/lib.rs
@@ -29,6 +29,13 @@ use repr::*;
 use symbol::NativeType;
 use symbol::Symbol;
 
+pub use call::CallError;
+pub use callback::CallbackError;
+pub use dlfcn::DlfcnError;
+pub use ir::IRError;
+pub use r#static::StaticError;
+pub use repr::ReprError;
+
 #[cfg(not(target_pointer_width = "64"))]
 compile_error!("platform not supported");
 
diff --git a/ext/ffi/repr.rs b/ext/ffi/repr.rs
index 315e6d53bc..2f04f4feb4 100644
--- a/ext/ffi/repr.rs
+++ b/ext/ffi/repr.rs
@@ -1,9 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use crate::FfiPermissions;
-use deno_core::error::range_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::OpState;
@@ -12,16 +9,58 @@ use std::ffi::c_void;
 use std::ffi::CStr;
 use std::ptr;
 
+#[derive(Debug, thiserror::Error)]
+pub enum ReprError {
+  #[error("Invalid pointer to offset, pointer is null")]
+  InvalidOffset,
+  #[error("Invalid ArrayBuffer pointer, pointer is null")]
+  InvalidArrayBuffer,
+  #[error("Destination length is smaller than source length")]
+  DestinationLengthTooShort,
+  #[error("Invalid CString pointer, pointer is null")]
+  InvalidCString,
+  #[error("Invalid CString pointer, string exceeds max length")]
+  CStringTooLong,
+  #[error("Invalid bool pointer, pointer is null")]
+  InvalidBool,
+  #[error("Invalid u8 pointer, pointer is null")]
+  InvalidU8,
+  #[error("Invalid i8 pointer, pointer is null")]
+  InvalidI8,
+  #[error("Invalid u16 pointer, pointer is null")]
+  InvalidU16,
+  #[error("Invalid i16 pointer, pointer is null")]
+  InvalidI16,
+  #[error("Invalid u32 pointer, pointer is null")]
+  InvalidU32,
+  #[error("Invalid i32 pointer, pointer is null")]
+  InvalidI32,
+  #[error("Invalid u64 pointer, pointer is null")]
+  InvalidU64,
+  #[error("Invalid i64 pointer, pointer is null")]
+  InvalidI64,
+  #[error("Invalid f32 pointer, pointer is null")]
+  InvalidF32,
+  #[error("Invalid f64 pointer, pointer is null")]
+  InvalidF64,
+  #[error("Invalid pointer pointer, pointer is null")]
+  InvalidPointer,
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+}
+
 #[op2(fast)]
 pub fn op_ffi_ptr_create<FP>(
   state: &mut OpState,
   #[bigint] ptr_number: usize,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   Ok(ptr_number as *mut c_void)
 }
@@ -31,12 +70,14 @@ pub fn op_ffi_ptr_equals<FP>(
   state: &mut OpState,
   a: *const c_void,
   b: *const c_void,
-) -> Result<bool, AnyError>
+) -> Result<bool, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   Ok(a == b)
 }
@@ -45,12 +86,14 @@ where
 pub fn op_ffi_ptr_of<FP>(
   state: &mut OpState,
   #[anybuffer] buf: *const u8,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   Ok(buf as *mut c_void)
 }
@@ -59,12 +102,14 @@ where
 pub fn op_ffi_ptr_of_exact<FP>(
   state: &mut OpState,
   buf: v8::Local<v8::ArrayBufferView>,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   let Some(buf) = buf.get_backing_store() else {
     return Ok(0 as _);
@@ -80,15 +125,17 @@ pub fn op_ffi_ptr_offset<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid pointer to offset, pointer is null"));
+    return Err(ReprError::InvalidOffset);
   }
 
   // TODO(mmastrac): Create a RawPointer that can safely do pointer math.
@@ -110,12 +157,14 @@ unsafe extern "C" fn noop_deleter_callback(
 pub fn op_ffi_ptr_value<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
-) -> Result<usize, AnyError>
+) -> Result<usize, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   Ok(ptr as usize)
 }
@@ -127,15 +176,17 @@ pub fn op_ffi_get_buf<FP, 'scope>(
   ptr: *mut c_void,
   #[number] offset: isize,
   #[number] len: usize,
-) -> Result<v8::Local<'scope, v8::ArrayBuffer>, AnyError>
+) -> Result<v8::Local<'scope, v8::ArrayBuffer>, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid ArrayBuffer pointer, pointer is null"));
+    return Err(ReprError::InvalidArrayBuffer);
   }
 
   // SAFETY: Trust the user to have provided a real pointer, offset, and a valid matching size to it. Since this is a foreign pointer, we should not do any deletion.
@@ -144,7 +195,7 @@ where
       ptr.offset(offset),
       len,
       noop_deleter_callback,
-      std::ptr::null_mut(),
+      ptr::null_mut(),
     )
   }
   .make_shared();
@@ -159,19 +210,19 @@ pub fn op_ffi_buf_copy_into<FP>(
   #[number] offset: isize,
   #[anybuffer] dst: &mut [u8],
   #[number] len: usize,
-) -> Result<(), AnyError>
+) -> Result<(), ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if src.is_null() {
-    Err(type_error("Invalid ArrayBuffer pointer, pointer is null"))
+    Err(ReprError::InvalidArrayBuffer)
   } else if dst.len() < len {
-    Err(range_error(
-      "Destination length is smaller than source length",
-    ))
+    Err(ReprError::DestinationLengthTooShort)
   } else {
     let src = src as *const c_void;
 
@@ -190,24 +241,24 @@ pub fn op_ffi_cstr_read<FP, 'scope>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<v8::Local<'scope, v8::String>, AnyError>
+) -> Result<v8::Local<'scope, v8::String>, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid CString pointer, pointer is null"));
+    return Err(ReprError::InvalidCString);
   }
 
   let cstr =
   // SAFETY: Pointer and offset are user provided.
     unsafe { CStr::from_ptr(ptr.offset(offset) as *const c_char) }.to_bytes();
   let value = v8::String::new_from_utf8(scope, cstr, v8::NewStringType::Normal)
-    .ok_or_else(|| {
-      type_error("Invalid CString pointer, string exceeds max length")
-    })?;
+    .ok_or_else(|| ReprError::CStringTooLong)?;
   Ok(value)
 }
 
@@ -216,15 +267,17 @@ pub fn op_ffi_read_bool<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<bool, AnyError>
+) -> Result<bool, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid bool pointer, pointer is null"));
+    return Err(ReprError::InvalidBool);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -236,15 +289,17 @@ pub fn op_ffi_read_u8<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<u32, AnyError>
+) -> Result<u32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid u8 pointer, pointer is null"));
+    return Err(ReprError::InvalidU8);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -258,15 +313,17 @@ pub fn op_ffi_read_i8<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<i32, AnyError>
+) -> Result<i32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid i8 pointer, pointer is null"));
+    return Err(ReprError::InvalidI8);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -280,15 +337,17 @@ pub fn op_ffi_read_u16<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<u32, AnyError>
+) -> Result<u32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid u16 pointer, pointer is null"));
+    return Err(ReprError::InvalidU16);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -302,15 +361,17 @@ pub fn op_ffi_read_i16<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<i32, AnyError>
+) -> Result<i32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid i16 pointer, pointer is null"));
+    return Err(ReprError::InvalidI16);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -324,15 +385,17 @@ pub fn op_ffi_read_u32<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<u32, AnyError>
+) -> Result<u32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid u32 pointer, pointer is null"));
+    return Err(ReprError::InvalidU32);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -344,15 +407,17 @@ pub fn op_ffi_read_i32<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<i32, AnyError>
+) -> Result<i32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid i32 pointer, pointer is null"));
+    return Err(ReprError::InvalidI32);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -367,15 +432,17 @@ pub fn op_ffi_read_u64<FP>(
   // Note: The representation of 64-bit integers is function-wide. We cannot
   // choose to take this parameter as a number while returning a bigint.
   #[bigint] offset: isize,
-) -> Result<u64, AnyError>
+) -> Result<u64, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid u64 pointer, pointer is null"));
+    return Err(ReprError::InvalidU64);
   }
 
   let value =
@@ -393,15 +460,17 @@ pub fn op_ffi_read_i64<FP>(
   // Note: The representation of 64-bit integers is function-wide. We cannot
   // choose to take this parameter as a number while returning a bigint.
   #[bigint] offset: isize,
-) -> Result<i64, AnyError>
+) -> Result<i64, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid i64 pointer, pointer is null"));
+    return Err(ReprError::InvalidI64);
   }
 
   let value =
@@ -416,15 +485,17 @@ pub fn op_ffi_read_f32<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<f32, AnyError>
+) -> Result<f32, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid f32 pointer, pointer is null"));
+    return Err(ReprError::InvalidF32);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -436,15 +507,17 @@ pub fn op_ffi_read_f64<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<f64, AnyError>
+) -> Result<f64, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid f64 pointer, pointer is null"));
+    return Err(ReprError::InvalidF64);
   }
 
   // SAFETY: ptr and offset are user provided.
@@ -456,15 +529,17 @@ pub fn op_ffi_read_ptr<FP>(
   state: &mut OpState,
   ptr: *mut c_void,
   #[number] offset: isize,
-) -> Result<*mut c_void, AnyError>
+) -> Result<*mut c_void, ReprError>
 where
   FP: FfiPermissions + 'static,
 {
   let permissions = state.borrow_mut::<FP>();
-  permissions.check_partial_no_path()?;
+  permissions
+    .check_partial_no_path()
+    .map_err(ReprError::Permission)?;
 
   if ptr.is_null() {
-    return Err(type_error("Invalid pointer pointer, pointer is null"));
+    return Err(ReprError::InvalidPointer);
   }
 
   // SAFETY: ptr and offset are user provided.
diff --git a/ext/ffi/static.rs b/ext/ffi/static.rs
index f08605754b..61b4059336 100644
--- a/ext/ffi/static.rs
+++ b/ext/ffi/static.rs
@@ -2,14 +2,24 @@
 
 use crate::dlfcn::DynamicLibraryResource;
 use crate::symbol::NativeType;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::OpState;
 use deno_core::ResourceId;
 use std::ptr;
 
+#[derive(Debug, thiserror::Error)]
+pub enum StaticError {
+  #[error(transparent)]
+  Dlfcn(super::DlfcnError),
+  #[error("Invalid FFI static type 'void'")]
+  InvalidTypeVoid,
+  #[error("Invalid FFI static type 'struct'")]
+  InvalidTypeStruct,
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+}
+
 #[op2]
 pub fn op_ffi_get_static<'scope>(
   scope: &mut v8::HandleScope<'scope>,
@@ -18,24 +28,27 @@ pub fn op_ffi_get_static<'scope>(
   #[string] name: String,
   #[serde] static_type: NativeType,
   optional: bool,
-) -> Result<v8::Local<'scope, v8::Value>, AnyError> {
-  let resource = state.resource_table.get::<DynamicLibraryResource>(rid)?;
+) -> Result<v8::Local<'scope, v8::Value>, StaticError> {
+  let resource = state
+    .resource_table
+    .get::<DynamicLibraryResource>(rid)
+    .map_err(StaticError::Resource)?;
 
   let data_ptr = match resource.get_static(name) {
-    Ok(data_ptr) => Ok(data_ptr),
+    Ok(data_ptr) => data_ptr,
     Err(err) => {
       if optional {
         let null: v8::Local<v8::Value> = v8::null(scope).into();
         return Ok(null);
       } else {
-        Err(err)
+        return Err(StaticError::Dlfcn(err));
       }
     }
-  }?;
+  };
 
   Ok(match static_type {
     NativeType::Void => {
-      return Err(type_error("Invalid FFI static type 'void'"));
+      return Err(StaticError::InvalidTypeVoid);
     }
     NativeType::Bool => {
       // SAFETY: ptr is user provided
@@ -132,7 +145,7 @@ pub fn op_ffi_get_static<'scope>(
       external
     }
     NativeType::Struct(_) => {
-      return Err(type_error("Invalid FFI static type 'struct'"));
+      return Err(StaticError::InvalidTypeStruct);
     }
   })
 }
diff --git a/ext/fs/Cargo.toml b/ext/fs/Cargo.toml
index 606c00ad8c..0ccde7f7e2 100644
--- a/ext/fs/Cargo.toml
+++ b/ext/fs/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_fs"
-version = "0.81.0"
+version = "0.85.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -28,9 +28,10 @@ libc.workspace = true
 rand.workspace = true
 rayon = "1.8.0"
 serde.workspace = true
+thiserror.workspace = true
 
 [target.'cfg(unix)'.dependencies]
-nix.workspace = true
+nix = { workspace = true, features = ["fs", "user"] }
 
 [target.'cfg(windows)'.dependencies]
 winapi = { workspace = true, features = ["winbase"] }
diff --git a/ext/fs/lib.rs b/ext/fs/lib.rs
index bd49078b2e..cd2baf22a9 100644
--- a/ext/fs/lib.rs
+++ b/ext/fs/lib.rs
@@ -14,6 +14,8 @@ pub use crate::interface::FileSystemRc;
 pub use crate::interface::FsDirEntry;
 pub use crate::interface::FsFileType;
 pub use crate::interface::OpenOptions;
+pub use crate::ops::FsOpsError;
+pub use crate::ops::OperationError;
 pub use crate::std_fs::RealFs;
 pub use crate::sync::MaybeSend;
 pub use crate::sync::MaybeSync;
diff --git a/ext/fs/ops.rs b/ext/fs/ops.rs
index b13d3a7d1a..a3f59da4ea 100644
--- a/ext/fs/ops.rs
+++ b/ext/fs/ops.rs
@@ -1,6 +1,8 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use std::cell::RefCell;
+use std::error::Error;
+use std::fmt::Formatter;
 use std::io;
 use std::io::SeekFrom;
 use std::path::Path;
@@ -8,10 +10,6 @@ use std::path::PathBuf;
 use std::path::StripPrefixError;
 use std::rc::Rc;
 
-use deno_core::anyhow::bail;
-use deno_core::error::custom_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::CancelFuture;
 use deno_core::CancelHandle;
@@ -34,6 +32,67 @@ use crate::interface::FsFileType;
 use crate::FsPermissions;
 use crate::OpenOptions;
 
+#[derive(Debug, thiserror::Error)]
+pub enum FsOpsError {
+  #[error("{0}")]
+  Io(#[source] std::io::Error),
+  #[error("{0}")]
+  OperationError(#[source] OperationError),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("File name or path {0:?} is not valid UTF-8")]
+  InvalidUtf8(std::ffi::OsString),
+  #[error("{0}")]
+  StripPrefix(#[from] StripPrefixError),
+  #[error("{0}")]
+  Canceled(#[from] deno_core::Canceled),
+  #[error("Invalid seek mode: {0}")]
+  InvalidSeekMode(i32),
+  #[error("Invalid control character in prefix or suffix: {0:?}")]
+  InvalidControlCharacter(String),
+  #[error("Invalid character in prefix or suffix: {0:?}")]
+  InvalidCharacter(String),
+  #[cfg(windows)]
+  #[error("Invalid trailing character in suffix")]
+  InvalidTrailingCharacter,
+  #[error("Requires {err} access to {path}, {}", print_not_capable_info(*.standalone, .err))]
+  NotCapableAccess {
+    // NotCapable
+    standalone: bool,
+    err: &'static str,
+    path: String,
+  },
+  #[error("permission denied: {0}")]
+  NotCapable(&'static str), // NotCapable
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
+impl From<FsError> for FsOpsError {
+  fn from(err: FsError) -> Self {
+    match err {
+      FsError::Io(err) => FsOpsError::Io(err),
+      FsError::FileBusy => {
+        FsOpsError::Other(deno_core::error::resource_unavailable())
+      }
+      FsError::NotSupported => {
+        FsOpsError::Other(deno_core::error::not_supported())
+      }
+      FsError::NotCapable(err) => FsOpsError::NotCapable(err),
+    }
+  }
+}
+
+fn print_not_capable_info(standalone: bool, err: &'static str) -> String {
+  if standalone {
+    format!("specify the required permissions during compilation using `deno compile --allow-{err}`")
+  } else {
+    format!("run again with the --allow-{err} flag")
+  }
+}
+
 fn sync_permission_check<'a, P: FsPermissions + 'static>(
   permissions: &'a mut P,
   api_name: &'static str,
@@ -58,7 +117,7 @@ fn map_permission_error(
   operation: &'static str,
   error: FsError,
   path: &Path,
-) -> AnyError {
+) -> FsOpsError {
   match error {
     FsError::NotCapable(err) => {
       let path = format!("{path:?}");
@@ -67,14 +126,12 @@ fn map_permission_error(
       } else {
         (path.as_str(), "")
       };
-      let msg = if deno_permissions::is_standalone() {
-        format!(
-          "Requires {err} access to {path}{truncated}, specify the required permissions during compilation using `deno compile --allow-{err}`")
-      } else {
-        format!(
-          "Requires {err} access to {path}{truncated}, run again with the --allow-{err} flag")
-      };
-      custom_error("NotCapable", msg)
+
+      FsOpsError::NotCapableAccess {
+        standalone: deno_permissions::is_standalone(),
+        err,
+        path: format!("{path}{truncated}"),
+      }
     }
     err => Err::<(), _>(err)
       .context_path(operation, path)
@@ -85,7 +142,7 @@ fn map_permission_error(
 
 #[op2]
 #[string]
-pub fn op_fs_cwd<P>(state: &mut OpState) -> Result<String, AnyError>
+pub fn op_fs_cwd<P>(state: &mut OpState) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -93,7 +150,8 @@ where
   let path = fs.cwd()?;
   state
     .borrow_mut::<P>()
-    .check_read_blind(&path, "CWD", "Deno.cwd()")?;
+    .check_read_blind(&path, "CWD", "Deno.cwd()")
+    .map_err(FsOpsError::Permission)?;
   let path_str = path_into_string(path.into_os_string())?;
   Ok(path_str)
 }
@@ -102,13 +160,14 @@ where
 pub fn op_fs_chdir<P>(
   state: &mut OpState,
   #[string] directory: &str,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let d = state
     .borrow_mut::<P>()
-    .check_read(directory, "Deno.chdir()")?;
+    .check_read(directory, "Deno.chdir()")
+    .map_err(FsOpsError::Permission)?;
   state
     .borrow::<FileSystemRc>()
     .chdir(&d)
@@ -119,7 +178,7 @@ where
 pub fn op_fs_umask(
   state: &mut OpState,
   mask: Option<u32>,
-) -> Result<u32, AnyError>
+) -> Result<u32, FsOpsError>
 where
 {
   state.borrow::<FileSystemRc>().umask(mask).context("umask")
@@ -131,7 +190,7 @@ pub fn op_fs_open_sync<P>(
   state: &mut OpState,
   #[string] path: String,
   #[serde] options: Option<OpenOptions>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -158,7 +217,7 @@ pub async fn op_fs_open_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[serde] options: Option<OpenOptions>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -186,7 +245,7 @@ pub fn op_fs_mkdir_sync<P>(
   #[string] path: String,
   recursive: bool,
   mode: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -194,7 +253,8 @@ where
 
   let path = state
     .borrow_mut::<P>()
-    .check_write(&path, "Deno.mkdirSync()")?;
+    .check_write(&path, "Deno.mkdirSync()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.mkdir_sync(&path, recursive, Some(mode))
@@ -209,7 +269,7 @@ pub async fn op_fs_mkdir_async<P>(
   #[string] path: String,
   recursive: bool,
   mode: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -217,7 +277,10 @@ where
 
   let (fs, path) = {
     let mut state = state.borrow_mut();
-    let path = state.borrow_mut::<P>().check_write(&path, "Deno.mkdir()")?;
+    let path = state
+      .borrow_mut::<P>()
+      .check_write(&path, "Deno.mkdir()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -233,13 +296,14 @@ pub fn op_fs_chmod_sync<P>(
   state: &mut OpState,
   #[string] path: String,
   mode: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write(&path, "Deno.chmodSync()")?;
+    .check_write(&path, "Deno.chmodSync()")
+    .map_err(FsOpsError::Permission)?;
   let fs = state.borrow::<FileSystemRc>();
   fs.chmod_sync(&path, mode).context_path("chmod", &path)?;
   Ok(())
@@ -250,13 +314,16 @@ pub async fn op_fs_chmod_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   mode: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let (fs, path) = {
     let mut state = state.borrow_mut();
-    let path = state.borrow_mut::<P>().check_write(&path, "Deno.chmod()")?;
+    let path = state
+      .borrow_mut::<P>()
+      .check_write(&path, "Deno.chmod()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
   fs.chmod_async(path.clone(), mode)
@@ -271,13 +338,14 @@ pub fn op_fs_chown_sync<P>(
   #[string] path: String,
   uid: Option<u32>,
   gid: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write(&path, "Deno.chownSync()")?;
+    .check_write(&path, "Deno.chownSync()")
+    .map_err(FsOpsError::Permission)?;
   let fs = state.borrow::<FileSystemRc>();
   fs.chown_sync(&path, uid, gid)
     .context_path("chown", &path)?;
@@ -290,13 +358,16 @@ pub async fn op_fs_chown_async<P>(
   #[string] path: String,
   uid: Option<u32>,
   gid: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let (fs, path) = {
     let mut state = state.borrow_mut();
-    let path = state.borrow_mut::<P>().check_write(&path, "Deno.chown()")?;
+    let path = state
+      .borrow_mut::<P>()
+      .check_write(&path, "Deno.chown()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
   fs.chown_async(path.clone(), uid, gid)
@@ -310,13 +381,14 @@ pub fn op_fs_remove_sync<P>(
   state: &mut OpState,
   #[string] path: &str,
   recursive: bool,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write(path, "Deno.removeSync()")?;
+    .check_write(path, "Deno.removeSync()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.remove_sync(&path, recursive)
@@ -330,7 +402,7 @@ pub async fn op_fs_remove_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   recursive: bool,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -339,11 +411,13 @@ where
     let path = if recursive {
       state
         .borrow_mut::<P>()
-        .check_write(&path, "Deno.remove()")?
+        .check_write(&path, "Deno.remove()")
+        .map_err(FsOpsError::Permission)?
     } else {
       state
         .borrow_mut::<P>()
-        .check_write_partial(&path, "Deno.remove()")?
+        .check_write_partial(&path, "Deno.remove()")
+        .map_err(FsOpsError::Permission)?
     };
 
     (state.borrow::<FileSystemRc>().clone(), path)
@@ -361,13 +435,17 @@ pub fn op_fs_copy_file_sync<P>(
   state: &mut OpState,
   #[string] from: &str,
   #[string] to: &str,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let permissions = state.borrow_mut::<P>();
-  let from = permissions.check_read(from, "Deno.copyFileSync()")?;
-  let to = permissions.check_write(to, "Deno.copyFileSync()")?;
+  let from = permissions
+    .check_read(from, "Deno.copyFileSync()")
+    .map_err(FsOpsError::Permission)?;
+  let to = permissions
+    .check_write(to, "Deno.copyFileSync()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.copy_file_sync(&from, &to)
@@ -381,15 +459,19 @@ pub async fn op_fs_copy_file_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] from: String,
   #[string] to: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let (fs, from, to) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    let from = permissions.check_read(&from, "Deno.copyFile()")?;
-    let to = permissions.check_write(&to, "Deno.copyFile()")?;
+    let from = permissions
+      .check_read(&from, "Deno.copyFile()")
+      .map_err(FsOpsError::Permission)?;
+    let to = permissions
+      .check_write(&to, "Deno.copyFile()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), from, to)
   };
 
@@ -405,13 +487,14 @@ pub fn op_fs_stat_sync<P>(
   state: &mut OpState,
   #[string] path: String,
   #[buffer] stat_out_buf: &mut [u32],
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_read(&path, "Deno.statSync()")?;
+    .check_read(&path, "Deno.statSync()")
+    .map_err(FsOpsError::Permission)?;
   let fs = state.borrow::<FileSystemRc>();
   let stat = fs.stat_sync(&path).context_path("stat", &path)?;
   let serializable_stat = SerializableStat::from(stat);
@@ -424,14 +507,16 @@ where
 pub async fn op_fs_stat_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<SerializableStat, AnyError>
+) -> Result<SerializableStat, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let (fs, path) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    let path = permissions.check_read(&path, "Deno.stat()")?;
+    let path = permissions
+      .check_read(&path, "Deno.stat()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
   let stat = fs
@@ -446,13 +531,14 @@ pub fn op_fs_lstat_sync<P>(
   state: &mut OpState,
   #[string] path: String,
   #[buffer] stat_out_buf: &mut [u32],
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_read(&path, "Deno.lstatSync()")?;
+    .check_read(&path, "Deno.lstatSync()")
+    .map_err(FsOpsError::Permission)?;
   let fs = state.borrow::<FileSystemRc>();
   let stat = fs.lstat_sync(&path).context_path("lstat", &path)?;
   let serializable_stat = SerializableStat::from(stat);
@@ -465,14 +551,16 @@ where
 pub async fn op_fs_lstat_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<SerializableStat, AnyError>
+) -> Result<SerializableStat, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let (fs, path) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    let path = permissions.check_read(&path, "Deno.lstat()")?;
+    let path = permissions
+      .check_read(&path, "Deno.lstat()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
   let stat = fs
@@ -487,15 +575,19 @@ where
 pub fn op_fs_realpath_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let fs = state.borrow::<FileSystemRc>().clone();
   let permissions = state.borrow_mut::<P>();
-  let path = permissions.check_read(&path, "Deno.realPathSync()")?;
+  let path = permissions
+    .check_read(&path, "Deno.realPathSync()")
+    .map_err(FsOpsError::Permission)?;
   if path.is_relative() {
-    permissions.check_read_blind(&fs.cwd()?, "CWD", "Deno.realPathSync()")?;
+    permissions
+      .check_read_blind(&fs.cwd()?, "CWD", "Deno.realPathSync()")
+      .map_err(FsOpsError::Permission)?;
   }
 
   let resolved_path =
@@ -510,7 +602,7 @@ where
 pub async fn op_fs_realpath_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -518,9 +610,13 @@ where
     let mut state = state.borrow_mut();
     let fs = state.borrow::<FileSystemRc>().clone();
     let permissions = state.borrow_mut::<P>();
-    let path = permissions.check_read(&path, "Deno.realPath()")?;
+    let path = permissions
+      .check_read(&path, "Deno.realPath()")
+      .map_err(FsOpsError::Permission)?;
     if path.is_relative() {
-      permissions.check_read_blind(&fs.cwd()?, "CWD", "Deno.realPath()")?;
+      permissions
+        .check_read_blind(&fs.cwd()?, "CWD", "Deno.realPath()")
+        .map_err(FsOpsError::Permission)?;
     }
     (fs, path)
   };
@@ -538,13 +634,14 @@ where
 pub fn op_fs_read_dir_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<Vec<FsDirEntry>, AnyError>
+) -> Result<Vec<FsDirEntry>, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_read(&path, "Deno.readDirSync()")?;
+    .check_read(&path, "Deno.readDirSync()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   let entries = fs.read_dir_sync(&path).context_path("readdir", &path)?;
@@ -557,7 +654,7 @@ where
 pub async fn op_fs_read_dir_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<Vec<FsDirEntry>, AnyError>
+) -> Result<Vec<FsDirEntry>, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -565,7 +662,8 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_read(&path, "Deno.readDir()")?;
+      .check_read(&path, "Deno.readDir()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -582,14 +680,20 @@ pub fn op_fs_rename_sync<P>(
   state: &mut OpState,
   #[string] oldpath: String,
   #[string] newpath: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let permissions = state.borrow_mut::<P>();
-  let _ = permissions.check_read(&oldpath, "Deno.renameSync()")?;
-  let oldpath = permissions.check_write(&oldpath, "Deno.renameSync()")?;
-  let newpath = permissions.check_write(&newpath, "Deno.renameSync()")?;
+  let _ = permissions
+    .check_read(&oldpath, "Deno.renameSync()")
+    .map_err(FsOpsError::Permission)?;
+  let oldpath = permissions
+    .check_write(&oldpath, "Deno.renameSync()")
+    .map_err(FsOpsError::Permission)?;
+  let newpath = permissions
+    .check_write(&newpath, "Deno.renameSync()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.rename_sync(&oldpath, &newpath)
@@ -603,16 +707,22 @@ pub async fn op_fs_rename_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] oldpath: String,
   #[string] newpath: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let (fs, oldpath, newpath) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    _ = permissions.check_read(&oldpath, "Deno.rename()")?;
-    let oldpath = permissions.check_write(&oldpath, "Deno.rename()")?;
-    let newpath = permissions.check_write(&newpath, "Deno.rename()")?;
+    _ = permissions
+      .check_read(&oldpath, "Deno.rename()")
+      .map_err(FsOpsError::Permission)?;
+    let oldpath = permissions
+      .check_write(&oldpath, "Deno.rename()")
+      .map_err(FsOpsError::Permission)?;
+    let newpath = permissions
+      .check_write(&newpath, "Deno.rename()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), oldpath, newpath)
   };
 
@@ -628,15 +738,23 @@ pub fn op_fs_link_sync<P>(
   state: &mut OpState,
   #[string] oldpath: &str,
   #[string] newpath: &str,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let permissions = state.borrow_mut::<P>();
-  _ = permissions.check_read(oldpath, "Deno.linkSync()")?;
-  let oldpath = permissions.check_write(oldpath, "Deno.linkSync()")?;
-  _ = permissions.check_read(newpath, "Deno.linkSync()")?;
-  let newpath = permissions.check_write(newpath, "Deno.linkSync()")?;
+  _ = permissions
+    .check_read(oldpath, "Deno.linkSync()")
+    .map_err(FsOpsError::Permission)?;
+  let oldpath = permissions
+    .check_write(oldpath, "Deno.linkSync()")
+    .map_err(FsOpsError::Permission)?;
+  _ = permissions
+    .check_read(newpath, "Deno.linkSync()")
+    .map_err(FsOpsError::Permission)?;
+  let newpath = permissions
+    .check_write(newpath, "Deno.linkSync()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.link_sync(&oldpath, &newpath)
@@ -650,17 +768,25 @@ pub async fn op_fs_link_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] oldpath: String,
   #[string] newpath: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let (fs, oldpath, newpath) = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    _ = permissions.check_read(&oldpath, "Deno.link()")?;
-    let oldpath = permissions.check_write(&oldpath, "Deno.link()")?;
-    _ = permissions.check_read(&newpath, "Deno.link()")?;
-    let newpath = permissions.check_write(&newpath, "Deno.link()")?;
+    _ = permissions
+      .check_read(&oldpath, "Deno.link()")
+      .map_err(FsOpsError::Permission)?;
+    let oldpath = permissions
+      .check_write(&oldpath, "Deno.link()")
+      .map_err(FsOpsError::Permission)?;
+    _ = permissions
+      .check_read(&newpath, "Deno.link()")
+      .map_err(FsOpsError::Permission)?;
+    let newpath = permissions
+      .check_write(&newpath, "Deno.link()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), oldpath, newpath)
   };
 
@@ -677,7 +803,7 @@ pub fn op_fs_symlink_sync<P>(
   #[string] oldpath: &str,
   #[string] newpath: &str,
   #[serde] file_type: Option<FsFileType>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -685,8 +811,12 @@ where
   let newpath = PathBuf::from(newpath);
 
   let permissions = state.borrow_mut::<P>();
-  permissions.check_write_all("Deno.symlinkSync()")?;
-  permissions.check_read_all("Deno.symlinkSync()")?;
+  permissions
+    .check_write_all("Deno.symlinkSync()")
+    .map_err(FsOpsError::Permission)?;
+  permissions
+    .check_read_all("Deno.symlinkSync()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.symlink_sync(&oldpath, &newpath, file_type)
@@ -701,7 +831,7 @@ pub async fn op_fs_symlink_async<P>(
   #[string] oldpath: String,
   #[string] newpath: String,
   #[serde] file_type: Option<FsFileType>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -711,8 +841,12 @@ where
   let fs = {
     let mut state = state.borrow_mut();
     let permissions = state.borrow_mut::<P>();
-    permissions.check_write_all("Deno.symlink()")?;
-    permissions.check_read_all("Deno.symlink()")?;
+    permissions
+      .check_write_all("Deno.symlink()")
+      .map_err(FsOpsError::Permission)?;
+    permissions
+      .check_read_all("Deno.symlink()")
+      .map_err(FsOpsError::Permission)?;
     state.borrow::<FileSystemRc>().clone()
   };
 
@@ -728,13 +862,14 @@ where
 pub fn op_fs_read_link_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_read(&path, "Deno.readLink()")?;
+    .check_read(&path, "Deno.readLink()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
 
@@ -748,7 +883,7 @@ where
 pub async fn op_fs_read_link_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -756,7 +891,8 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_read(&path, "Deno.readLink()")?;
+      .check_read(&path, "Deno.readLink()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -773,13 +909,14 @@ pub fn op_fs_truncate_sync<P>(
   state: &mut OpState,
   #[string] path: &str,
   #[number] len: u64,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write(path, "Deno.truncateSync()")?;
+    .check_write(path, "Deno.truncateSync()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.truncate_sync(&path, len)
@@ -793,7 +930,7 @@ pub async fn op_fs_truncate_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[number] len: u64,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -801,7 +938,8 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_write(&path, "Deno.truncate()")?;
+      .check_write(&path, "Deno.truncate()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -820,11 +958,14 @@ pub fn op_fs_utime_sync<P>(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
-  let path = state.borrow_mut::<P>().check_write(path, "Deno.utime()")?;
+  let path = state
+    .borrow_mut::<P>()
+    .check_write(path, "Deno.utime()")
+    .map_err(FsOpsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.utime_sync(&path, atime_secs, atime_nanos, mtime_secs, mtime_nanos)
@@ -841,13 +982,16 @@ pub async fn op_fs_utime_async<P>(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let (fs, path) = {
     let mut state = state.borrow_mut();
-    let path = state.borrow_mut::<P>().check_write(&path, "Deno.utime()")?;
+    let path = state
+      .borrow_mut::<P>()
+      .check_write(&path, "Deno.utime()")
+      .map_err(FsOpsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -871,7 +1015,7 @@ pub fn op_fs_make_temp_dir_sync<P>(
   #[string] dir_arg: Option<String>,
   #[string] prefix: Option<String>,
   #[string] suffix: Option<String>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -913,7 +1057,7 @@ pub async fn op_fs_make_temp_dir_async<P>(
   #[string] dir_arg: Option<String>,
   #[string] prefix: Option<String>,
   #[string] suffix: Option<String>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -959,7 +1103,7 @@ pub fn op_fs_make_temp_file_sync<P>(
   #[string] dir_arg: Option<String>,
   #[string] prefix: Option<String>,
   #[string] suffix: Option<String>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1007,7 +1151,7 @@ pub async fn op_fs_make_temp_file_async<P>(
   #[string] dir_arg: Option<String>,
   #[string] prefix: Option<String>,
   #[string] suffix: Option<String>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1069,18 +1213,22 @@ fn make_temp_check_sync<P>(
   state: &mut OpState,
   dir: Option<&str>,
   api_name: &str,
-) -> Result<(PathBuf, FileSystemRc), AnyError>
+) -> Result<(PathBuf, FileSystemRc), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let fs = state.borrow::<FileSystemRc>().clone();
   let dir = match dir {
-    Some(dir) => state.borrow_mut::<P>().check_write(dir, api_name)?,
+    Some(dir) => state
+      .borrow_mut::<P>()
+      .check_write(dir, api_name)
+      .map_err(FsOpsError::Permission)?,
     None => {
       let dir = fs.tmp_dir().context("tmpdir")?;
       state
         .borrow_mut::<P>()
-        .check_write_blind(&dir, "TMP", api_name)?;
+        .check_write_blind(&dir, "TMP", api_name)
+        .map_err(FsOpsError::Permission)?;
       dir
     }
   };
@@ -1091,19 +1239,23 @@ fn make_temp_check_async<P>(
   state: Rc<RefCell<OpState>>,
   dir: Option<&str>,
   api_name: &str,
-) -> Result<(PathBuf, FileSystemRc), AnyError>
+) -> Result<(PathBuf, FileSystemRc), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
   let mut state = state.borrow_mut();
   let fs = state.borrow::<FileSystemRc>().clone();
   let dir = match dir {
-    Some(dir) => state.borrow_mut::<P>().check_write(dir, api_name)?,
+    Some(dir) => state
+      .borrow_mut::<P>()
+      .check_write(dir, api_name)
+      .map_err(FsOpsError::Permission)?,
     None => {
       let dir = fs.tmp_dir().context("tmpdir")?;
       state
         .borrow_mut::<P>()
-        .check_write_blind(&dir, "TMP", api_name)?;
+        .check_write_blind(&dir, "TMP", api_name)
+        .map_err(FsOpsError::Permission)?;
       dir
     }
   };
@@ -1116,10 +1268,10 @@ where
 fn validate_temporary_filename_component(
   component: &str,
   #[allow(unused_variables)] suffix: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), FsOpsError> {
   // Ban ASCII and Unicode control characters: these will often fail
   if let Some(c) = component.matches(|c: char| c.is_control()).next() {
-    bail!("Invalid control character in prefix or suffix: {:?}", c);
+    return Err(FsOpsError::InvalidControlCharacter(c.to_string()));
   }
   // Windows has the most restrictive filenames. As temp files aren't normal files, we just
   // use this set of banned characters for all platforms because wildcard-like files can also
@@ -1135,13 +1287,13 @@ fn validate_temporary_filename_component(
     .matches(|c: char| "<>:\"/\\|?*".contains(c))
     .next()
   {
-    bail!("Invalid character in prefix or suffix: {:?}", c);
+    return Err(FsOpsError::InvalidCharacter(c.to_string()));
   }
 
   // This check is only for Windows
   #[cfg(windows)]
   if suffix && component.ends_with(|c: char| ". ".contains(c)) {
-    bail!("Invalid trailing character in suffix");
+    return Err(FsOpsError::InvalidTrailingCharacter);
   }
 
   Ok(())
@@ -1152,7 +1304,7 @@ fn tmp_name(
   dir: &Path,
   prefix: Option<&str>,
   suffix: Option<&str>,
-) -> Result<PathBuf, AnyError> {
+) -> Result<PathBuf, FsOpsError> {
   let prefix = prefix.unwrap_or("");
   validate_temporary_filename_component(prefix, false)?;
   let suffix = suffix.unwrap_or("");
@@ -1179,7 +1331,7 @@ pub fn op_fs_write_file_sync<P>(
   create: bool,
   create_new: bool,
   #[buffer] data: JsBuffer,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1207,7 +1359,7 @@ pub async fn op_fs_write_file_async<P>(
   create_new: bool,
   #[buffer] data: JsBuffer,
   #[smi] cancel_rid: Option<ResourceId>,
-) -> Result<(), AnyError>
+) -> Result<(), FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1255,7 +1407,7 @@ where
 pub fn op_fs_read_file_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<ToJsBuffer, AnyError>
+) -> Result<ToJsBuffer, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1277,7 +1429,7 @@ pub async fn op_fs_read_file_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[smi] cancel_rid: Option<ResourceId>,
-) -> Result<ToJsBuffer, AnyError>
+) -> Result<ToJsBuffer, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1318,7 +1470,7 @@ where
 pub fn op_fs_read_file_text_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1340,7 +1492,7 @@ pub async fn op_fs_read_file_text_async<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[smi] cancel_rid: Option<ResourceId>,
-) -> Result<String, AnyError>
+) -> Result<String, FsOpsError>
 where
   P: FsPermissions + 'static,
 {
@@ -1377,13 +1529,13 @@ where
   Ok(str)
 }
 
-fn to_seek_from(offset: i64, whence: i32) -> Result<SeekFrom, AnyError> {
+fn to_seek_from(offset: i64, whence: i32) -> Result<SeekFrom, FsOpsError> {
   let seek_from = match whence {
     0 => SeekFrom::Start(offset as u64),
     1 => SeekFrom::Current(offset),
     2 => SeekFrom::End(offset),
     _ => {
-      return Err(type_error(format!("Invalid seek mode: {whence}")));
+      return Err(FsOpsError::InvalidSeekMode(whence));
     }
   };
   Ok(seek_from)
@@ -1396,9 +1548,10 @@ pub fn op_fs_seek_sync(
   #[smi] rid: ResourceId,
   #[number] offset: i64,
   #[smi] whence: i32,
-) -> Result<u64, AnyError> {
+) -> Result<u64, FsOpsError> {
   let pos = to_seek_from(offset, whence)?;
-  let file = FileResource::get_file(state, rid)?;
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   let cursor = file.seek_sync(pos)?;
   Ok(cursor)
 }
@@ -1410,9 +1563,10 @@ pub async fn op_fs_seek_async(
   #[smi] rid: ResourceId,
   #[number] offset: i64,
   #[smi] whence: i32,
-) -> Result<u64, AnyError> {
+) -> Result<u64, FsOpsError> {
   let pos = to_seek_from(offset, whence)?;
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   let cursor = file.seek_async(pos).await?;
   Ok(cursor)
 }
@@ -1421,8 +1575,9 @@ pub async fn op_fs_seek_async(
 pub fn op_fs_file_sync_data_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.datasync_sync()?;
   Ok(())
 }
@@ -1431,8 +1586,9 @@ pub fn op_fs_file_sync_data_sync(
 pub async fn op_fs_file_sync_data_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.datasync_async().await?;
   Ok(())
 }
@@ -1441,8 +1597,9 @@ pub async fn op_fs_file_sync_data_async(
 pub fn op_fs_file_sync_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.sync_sync()?;
   Ok(())
 }
@@ -1451,8 +1608,9 @@ pub fn op_fs_file_sync_sync(
 pub async fn op_fs_file_sync_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.sync_async().await?;
   Ok(())
 }
@@ -1462,8 +1620,9 @@ pub fn op_fs_file_stat_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[buffer] stat_out_buf: &mut [u32],
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   let stat = file.stat_sync()?;
   let serializable_stat = SerializableStat::from(stat);
   serializable_stat.write(stat_out_buf);
@@ -1475,8 +1634,9 @@ pub fn op_fs_file_stat_sync(
 pub async fn op_fs_file_stat_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<SerializableStat, AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<SerializableStat, FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   let stat = file.stat_async().await?;
   Ok(stat.into())
 }
@@ -1486,8 +1646,9 @@ pub fn op_fs_flock_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   exclusive: bool,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.lock_sync(exclusive)?;
   Ok(())
 }
@@ -1497,8 +1658,9 @@ pub async fn op_fs_flock_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   exclusive: bool,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.lock_async(exclusive).await?;
   Ok(())
 }
@@ -1507,8 +1669,9 @@ pub async fn op_fs_flock_async(
 pub fn op_fs_funlock_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.unlock_sync()?;
   Ok(())
 }
@@ -1517,8 +1680,9 @@ pub fn op_fs_funlock_sync(
 pub async fn op_fs_funlock_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.unlock_async().await?;
   Ok(())
 }
@@ -1528,8 +1692,9 @@ pub fn op_fs_ftruncate_sync(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[number] len: u64,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.truncate_sync(len)?;
   Ok(())
 }
@@ -1539,8 +1704,9 @@ pub async fn op_fs_file_truncate_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[number] len: u64,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file.truncate_async(len).await?;
   Ok(())
 }
@@ -1553,8 +1719,9 @@ pub fn op_fs_futime_sync(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(state, rid)?;
+) -> Result<(), FsOpsError> {
+  let file =
+    FileResource::get_file(state, rid).map_err(FsOpsError::Resource)?;
   file.utime_sync(atime_secs, atime_nanos, mtime_secs, mtime_nanos)?;
   Ok(())
 }
@@ -1567,42 +1734,64 @@ pub async fn op_fs_futime_async(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError> {
-  let file = FileResource::get_file(&state.borrow(), rid)?;
+) -> Result<(), FsOpsError> {
+  let file = FileResource::get_file(&state.borrow(), rid)
+    .map_err(FsOpsError::Resource)?;
   file
     .utime_async(atime_secs, atime_nanos, mtime_secs, mtime_nanos)
     .await?;
   Ok(())
 }
 
-trait WithContext {
-  fn context<E: Into<Box<dyn std::error::Error + Send + Sync>>>(
-    self,
-    desc: E,
-  ) -> AnyError;
+#[derive(Debug)]
+pub struct OperationError {
+  operation: &'static str,
+  kind: OperationErrorKind,
+  pub err: FsError,
 }
 
-impl WithContext for FsError {
-  fn context<E: Into<Box<dyn std::error::Error + Send + Sync>>>(
-    self,
-    desc: E,
-  ) -> AnyError {
-    match self {
-      FsError::Io(io) => {
-        AnyError::new(io::Error::new(io.kind(), desc)).context(io)
+impl std::fmt::Display for OperationError {
+  fn fmt(&self, f: &mut Formatter<'_>) -> std::fmt::Result {
+    if let FsError::Io(e) = &self.err {
+      std::fmt::Display::fmt(&e, f)?;
+      f.write_str(": ")?;
+    }
+
+    f.write_str(self.operation)?;
+
+    match &self.kind {
+      OperationErrorKind::Bare => Ok(()),
+      OperationErrorKind::WithPath(path) => write!(f, " '{}'", path.display()),
+      OperationErrorKind::WithTwoPaths(from, to) => {
+        write!(f, " '{}' -> '{}'", from.display(), to.display())
       }
-      _ => self.into(),
     }
   }
 }
 
+impl std::error::Error for OperationError {
+  fn source(&self) -> Option<&(dyn Error + 'static)> {
+    if let FsError::Io(err) = &self.err {
+      Some(err)
+    } else {
+      None
+    }
+  }
+}
+
+#[derive(Debug)]
+pub enum OperationErrorKind {
+  Bare,
+  WithPath(PathBuf),
+  WithTwoPaths(PathBuf, PathBuf),
+}
+
 trait MapErrContext {
   type R;
 
-  fn context_fn<F, E>(self, f: F) -> Self::R
+  fn context_fn<F>(self, f: F) -> Self::R
   where
-    F: FnOnce() -> E,
-    E: Into<Box<dyn std::error::Error + Send + Sync>>;
+    F: FnOnce(FsError) -> OperationError;
 
   fn context(self, desc: &'static str) -> Self::R;
 
@@ -1617,25 +1806,29 @@ trait MapErrContext {
 }
 
 impl<T> MapErrContext for Result<T, FsError> {
-  type R = Result<T, AnyError>;
+  type R = Result<T, FsOpsError>;
 
-  fn context_fn<F, E>(self, f: F) -> Self::R
+  fn context_fn<F>(self, f: F) -> Self::R
   where
-    F: FnOnce() -> E,
-    E: Into<Box<dyn std::error::Error + Send + Sync>>,
+    F: FnOnce(FsError) -> OperationError,
   {
-    self.map_err(|err| {
-      let message = f();
-      err.context(message)
+    self.map_err(|err| FsOpsError::OperationError(f(err)))
+  }
+
+  fn context(self, operation: &'static str) -> Self::R {
+    self.context_fn(move |err| OperationError {
+      operation,
+      kind: OperationErrorKind::Bare,
+      err,
     })
   }
 
-  fn context(self, desc: &'static str) -> Self::R {
-    self.context_fn(move || desc)
-  }
-
   fn context_path(self, operation: &'static str, path: &Path) -> Self::R {
-    self.context_fn(|| format!("{operation} '{}'", path.display()))
+    self.context_fn(|err| OperationError {
+      operation,
+      kind: OperationErrorKind::WithPath(path.to_path_buf()),
+      err,
+    })
   }
 
   fn context_two_path(
@@ -1644,21 +1837,19 @@ impl<T> MapErrContext for Result<T, FsError> {
     oldpath: &Path,
     newpath: &Path,
   ) -> Self::R {
-    self.context_fn(|| {
-      format!(
-        "{operation} '{}' -> '{}'",
-        oldpath.display(),
-        newpath.display()
-      )
+    self.context_fn(|err| OperationError {
+      operation,
+      kind: OperationErrorKind::WithTwoPaths(
+        oldpath.to_path_buf(),
+        newpath.to_path_buf(),
+      ),
+      err,
     })
   }
 }
 
-fn path_into_string(s: std::ffi::OsString) -> Result<String, AnyError> {
-  s.into_string().map_err(|s| {
-    let message = format!("File name or path {s:?} is not valid UTF-8");
-    custom_error("InvalidData", message)
-  })
+fn path_into_string(s: std::ffi::OsString) -> Result<String, FsOpsError> {
+  s.into_string().map_err(FsOpsError::InvalidUtf8)
 }
 
 macro_rules! create_struct_writer {
diff --git a/ext/fs/std_fs.rs b/ext/fs/std_fs.rs
index 41a8569ba8..1a83c97c53 100644
--- a/ext/fs/std_fs.rs
+++ b/ext/fs/std_fs.rs
@@ -929,7 +929,7 @@ fn exists(path: &Path) -> bool {
 }
 
 fn realpath(path: &Path) -> FsResult<PathBuf> {
-  Ok(deno_core::strip_unc_prefix(path.canonicalize()?))
+  Ok(deno_path_util::strip_unc_prefix(path.canonicalize()?))
 }
 
 fn read_dir(path: &Path) -> FsResult<Vec<FsDirEntry>> {
diff --git a/ext/http/00_serve.ts b/ext/http/00_serve.ts
index 3b9b085a22..1b70cf2129 100644
--- a/ext/http/00_serve.ts
+++ b/ext/http/00_serve.ts
@@ -76,7 +76,11 @@ import {
   ReadableStreamPrototype,
   resourceForReadableStream,
 } from "ext:deno_web/06_streams.js";
-import { listen, listenOptionApiName, TcpConn } from "ext:deno_net/01_net.js";
+import {
+  listen,
+  listenOptionApiName,
+  UpgradedConn,
+} from "ext:deno_net/01_net.js";
 import { hasTlsKeyPairOptions, listenTls } from "ext:deno_net/02_tls.js";
 import { SymbolAsyncDispose } from "ext:deno_web/00_infra.js";
 
@@ -189,7 +193,7 @@ class InnerRequest {
 
       const upgradeRid = op_http_upgrade_raw(external);
 
-      const conn = new TcpConn(
+      const conn = new UpgradedConn(
         upgradeRid,
         underlyingConn?.remoteAddr,
         underlyingConn?.localAddr,
diff --git a/ext/http/Cargo.toml b/ext/http/Cargo.toml
index b7637bec33..a1a4cb20be 100644
--- a/ext/http/Cargo.toml
+++ b/ext/http/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_http"
-version = "0.169.0"
+version = "0.173.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/http/fly_accept_encoding.rs b/ext/http/fly_accept_encoding.rs
index 94e3368767..4d6fd2231e 100644
--- a/ext/http/fly_accept_encoding.rs
+++ b/ext/http/fly_accept_encoding.rs
@@ -119,7 +119,7 @@ fn encodings_iter_inner<'s>(
       };
       Some(Ok((encoding, qval)))
     })
-    .map(|r| r?) // flatten Result<Result<...
+    .flatten()
 }
 
 #[cfg(test)]
diff --git a/ext/http/http_next.rs b/ext/http/http_next.rs
index efe1b88c93..56c46de925 100644
--- a/ext/http/http_next.rs
+++ b/ext/http/http_next.rs
@@ -19,7 +19,6 @@ use crate::service::SignallingRc;
 use crate::websocket_upgrade::WebSocketUpgrade;
 use crate::LocalExecutor;
 use cache_control::CacheControl;
-use deno_core::error::AnyError;
 use deno_core::external;
 use deno_core::futures::future::poll_fn;
 use deno_core::futures::TryFutureExt;
@@ -146,12 +145,32 @@ macro_rules! clone_external {
   }};
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpNextError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(#[from] io::Error),
+  #[error(transparent)]
+  WebSocketUpgrade(crate::websocket_upgrade::WebSocketUpgradeError),
+  #[error("{0}")]
+  Hyper(#[from] hyper::Error),
+  #[error(transparent)]
+  JoinError(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error(transparent)]
+  HttpPropertyExtractor(deno_core::error::AnyError),
+  #[error(transparent)]
+  UpgradeUnavailable(#[from] crate::service::UpgradeUnavailableError),
+}
+
 #[op2(fast)]
 #[smi]
 pub fn op_http_upgrade_raw(
   state: &mut OpState,
   external: *const c_void,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpNextError> {
   // SAFETY: external is deleted before calling this op.
   let http = unsafe { take_external!(external, "op_http_upgrade_raw") };
 
@@ -177,7 +196,7 @@ pub fn op_http_upgrade_raw(
           upgraded.write_all(&bytes).await?;
           break upgraded;
         }
-        Err(err) => return Err(err),
+        Err(err) => return Err(HttpNextError::WebSocketUpgrade(err)),
       }
     };
 
@@ -193,7 +212,7 @@ pub fn op_http_upgrade_raw(
         }
         read_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, HttpNextError>(())
     });
     spawn(async move {
       let mut buf = [0; 1024];
@@ -204,7 +223,7 @@ pub fn op_http_upgrade_raw(
         }
         upgraded_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, HttpNextError>(())
     });
 
     Ok(())
@@ -223,7 +242,7 @@ pub async fn op_http_upgrade_websocket_next(
   state: Rc<RefCell<OpState>>,
   external: *const c_void,
   #[serde] headers: Vec<(ByteString, ByteString)>,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpNextError> {
   let http =
     // SAFETY: external is deleted before calling this op.
     unsafe { take_external!(external, "op_http_upgrade_websocket_next") };
@@ -246,7 +265,11 @@ pub async fn op_http_upgrade_websocket_next(
 
   // Stage 3: take the extracted raw network stream and upgrade it to a websocket, then return it
   let (stream, bytes) = extract_network_stream(upgraded);
-  ws_create_server_stream(&mut state.borrow_mut(), stream, bytes)
+  Ok(ws_create_server_stream(
+    &mut state.borrow_mut(),
+    stream,
+    bytes,
+  ))
 }
 
 #[op2(fast)]
@@ -296,7 +319,7 @@ where
   let authority: v8::Local<v8::Value> = match request_properties.authority {
     Some(authority) => v8::String::new_from_utf8(
       scope,
-      authority.as_ref(),
+      authority.as_bytes(),
       v8::NewStringType::Normal,
     )
     .unwrap()
@@ -305,15 +328,25 @@ where
   };
 
   // Only extract the path part - we handle authority elsewhere
-  let path = match &request_parts.uri.path_and_query() {
-    Some(path_and_query) => path_and_query.to_string(),
-    None => "".to_owned(),
+  let path = match request_parts.uri.path_and_query() {
+    Some(path_and_query) => {
+      let path = path_and_query.as_str();
+      if matches!(path.as_bytes().first(), Some(b'/' | b'*')) {
+        Cow::Borrowed(path)
+      } else {
+        Cow::Owned(format!("/{}", path))
+      }
+    }
+    None => Cow::Borrowed(""),
   };
 
-  let path: v8::Local<v8::Value> =
-    v8::String::new_from_utf8(scope, path.as_ref(), v8::NewStringType::Normal)
-      .unwrap()
-      .into();
+  let path: v8::Local<v8::Value> = v8::String::new_from_utf8(
+    scope,
+    path.as_bytes(),
+    v8::NewStringType::Normal,
+  )
+  .unwrap()
+  .into();
 
   let peer_address: v8::Local<v8::Value> = v8::String::new_from_utf8(
     scope,
@@ -676,7 +709,7 @@ pub async fn op_http_set_response_body_resource(
   #[smi] stream_rid: ResourceId,
   auto_close: bool,
   status: u16,
-) -> Result<bool, AnyError> {
+) -> Result<bool, HttpNextError> {
   let http =
     // SAFETY: op is called with external.
     unsafe { clone_external!(external, "op_http_set_response_body_resource") };
@@ -691,9 +724,15 @@ pub async fn op_http_set_response_body_resource(
   let resource = {
     let mut state = state.borrow_mut();
     if auto_close {
-      state.resource_table.take_any(stream_rid)?
+      state
+        .resource_table
+        .take_any(stream_rid)
+        .map_err(HttpNextError::Resource)?
     } else {
-      state.resource_table.get_any(stream_rid)?
+      state
+        .resource_table
+        .get_any(stream_rid)
+        .map_err(HttpNextError::Resource)?
     }
   };
 
@@ -800,17 +839,17 @@ async fn serve_http2_autodetect(
   io: impl HttpServeStream,
   svc: impl HttpService<Incoming, ResBody = HttpRecordResponse> + 'static,
   cancel: Rc<CancelHandle>,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpNextError> {
   let prefix = NetworkStreamPrefixCheck::new(io, HTTP2_PREFIX);
   let (matches, io) = prefix.match_prefix().await?;
   if matches {
     serve_http2_unconditional(io, svc, cancel)
       .await
-      .map_err(|e| e.into())
+      .map_err(HttpNextError::Hyper)
   } else {
     serve_http11_unconditional(io, svc, cancel)
       .await
-      .map_err(|e| e.into())
+      .map_err(HttpNextError::Hyper)
   }
 }
 
@@ -819,7 +858,7 @@ fn serve_https(
   request_info: HttpConnectionProperties,
   lifetime: HttpLifetime,
   tx: tokio::sync::mpsc::Sender<Rc<HttpRecord>>,
-) -> JoinHandle<Result<(), AnyError>> {
+) -> JoinHandle<Result<(), HttpNextError>> {
   let HttpLifetime {
     server_state,
     connection_cancel_handle,
@@ -838,11 +877,11 @@ fn serve_https(
       if Some(TLS_ALPN_HTTP_2) == handshake.as_deref() {
         serve_http2_unconditional(io, svc, listen_cancel_handle)
           .await
-          .map_err(|e| e.into())
+          .map_err(HttpNextError::Hyper)
       } else if Some(TLS_ALPN_HTTP_11) == handshake.as_deref() {
         serve_http11_unconditional(io, svc, listen_cancel_handle)
           .await
-          .map_err(|e| e.into())
+          .map_err(HttpNextError::Hyper)
       } else {
         serve_http2_autodetect(io, svc, listen_cancel_handle).await
       }
@@ -856,7 +895,7 @@ fn serve_http(
   request_info: HttpConnectionProperties,
   lifetime: HttpLifetime,
   tx: tokio::sync::mpsc::Sender<Rc<HttpRecord>>,
-) -> JoinHandle<Result<(), AnyError>> {
+) -> JoinHandle<Result<(), HttpNextError>> {
   let HttpLifetime {
     server_state,
     connection_cancel_handle,
@@ -877,7 +916,7 @@ fn serve_http_on<HTTP>(
   listen_properties: &HttpListenProperties,
   lifetime: HttpLifetime,
   tx: tokio::sync::mpsc::Sender<Rc<HttpRecord>>,
-) -> JoinHandle<Result<(), AnyError>>
+) -> JoinHandle<Result<(), HttpNextError>>
 where
   HTTP: HttpPropertyExtractor,
 {
@@ -908,7 +947,7 @@ struct HttpLifetime {
 }
 
 struct HttpJoinHandle {
-  join_handle: AsyncRefCell<Option<JoinHandle<Result<(), AnyError>>>>,
+  join_handle: AsyncRefCell<Option<JoinHandle<Result<(), HttpNextError>>>>,
   connection_cancel_handle: Rc<CancelHandle>,
   listen_cancel_handle: Rc<CancelHandle>,
   rx: AsyncRefCell<tokio::sync::mpsc::Receiver<Rc<HttpRecord>>>,
@@ -968,12 +1007,13 @@ impl Drop for HttpJoinHandle {
 pub fn op_http_serve<HTTP>(
   state: Rc<RefCell<OpState>>,
   #[smi] listener_rid: ResourceId,
-) -> Result<(ResourceId, &'static str, String), AnyError>
+) -> Result<(ResourceId, &'static str, String), HttpNextError>
 where
   HTTP: HttpPropertyExtractor,
 {
   let listener =
-    HTTP::get_listener_for_rid(&mut state.borrow_mut(), listener_rid)?;
+    HTTP::get_listener_for_rid(&mut state.borrow_mut(), listener_rid)
+      .map_err(HttpNextError::Resource)?;
 
   let listen_properties = HTTP::listen_properties_from_listener(&listener)?;
 
@@ -988,7 +1028,8 @@ where
     loop {
       let conn = HTTP::accept_connection_from_listener(&listener)
         .try_or_cancel(listen_cancel_clone.clone())
-        .await?;
+        .await
+        .map_err(HttpNextError::HttpPropertyExtractor)?;
       serve_http_on::<HTTP>(
         conn,
         &listen_properties_clone,
@@ -997,7 +1038,7 @@ where
       );
     }
     #[allow(unreachable_code)]
-    Ok::<_, AnyError>(())
+    Ok::<_, HttpNextError>(())
   });
 
   // Set the handle after we start the future
@@ -1017,25 +1058,25 @@ where
 pub fn op_http_serve_on<HTTP>(
   state: Rc<RefCell<OpState>>,
   #[smi] connection_rid: ResourceId,
-) -> Result<(ResourceId, &'static str, String), AnyError>
+) -> Result<(ResourceId, &'static str, String), HttpNextError>
 where
   HTTP: HttpPropertyExtractor,
 {
   let connection =
-    HTTP::get_connection_for_rid(&mut state.borrow_mut(), connection_rid)?;
+    HTTP::get_connection_for_rid(&mut state.borrow_mut(), connection_rid)
+      .map_err(HttpNextError::Resource)?;
 
   let listen_properties = HTTP::listen_properties_from_connection(&connection)?;
 
   let (tx, rx) = tokio::sync::mpsc::channel(10);
   let resource: Rc<HttpJoinHandle> = Rc::new(HttpJoinHandle::new(rx));
 
-  let handle: JoinHandle<Result<(), deno_core::anyhow::Error>> =
-    serve_http_on::<HTTP>(
-      connection,
-      &listen_properties,
-      resource.lifetime(),
-      tx,
-    );
+  let handle = serve_http_on::<HTTP>(
+    connection,
+    &listen_properties,
+    resource.lifetime(),
+    tx,
+  );
 
   // Set the handle after we start the future
   *RcRef::map(&resource, |this| &this.join_handle)
@@ -1081,12 +1122,13 @@ pub fn op_http_try_wait(
 pub async fn op_http_wait(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<*const c_void, AnyError> {
+) -> Result<*const c_void, HttpNextError> {
   // We will get the join handle initially, as we might be consuming requests still
   let join_handle = state
     .borrow_mut()
     .resource_table
-    .get::<HttpJoinHandle>(rid)?;
+    .get::<HttpJoinHandle>(rid)
+    .map_err(HttpNextError::Resource)?;
 
   let cancel = join_handle.listen_cancel_handle();
   let next = async {
@@ -1113,13 +1155,12 @@ pub async fn op_http_wait(
 
   // Filter out shutdown (ENOTCONN) errors
   if let Err(err) = res {
-    if let Some(err) = err.source() {
-      if let Some(err) = err.downcast_ref::<io::Error>() {
-        if err.kind() == io::ErrorKind::NotConnected {
-          return Ok(null());
-        }
+    if let HttpNextError::Io(err) = &err {
+      if err.kind() == io::ErrorKind::NotConnected {
+        return Ok(null());
       }
     }
+
     return Err(err);
   }
 
@@ -1132,7 +1173,7 @@ pub fn op_http_cancel(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   graceful: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let join_handle = state.resource_table.get::<HttpJoinHandle>(rid)?;
 
   if graceful {
@@ -1152,11 +1193,12 @@ pub async fn op_http_close(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   graceful: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpNextError> {
   let join_handle = state
     .borrow_mut()
     .resource_table
-    .take::<HttpJoinHandle>(rid)?;
+    .take::<HttpJoinHandle>(rid)
+    .map_err(HttpNextError::Resource)?;
 
   if graceful {
     http_general_trace!("graceful shutdown");
@@ -1202,23 +1244,26 @@ impl UpgradeStream {
     }
   }
 
-  async fn read(self: Rc<Self>, buf: &mut [u8]) -> Result<usize, AnyError> {
+  async fn read(
+    self: Rc<Self>,
+    buf: &mut [u8],
+  ) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let read = RcRef::map(self, |this| &this.read);
       let mut read = read.borrow_mut().await;
-      Ok(Pin::new(&mut *read).read(buf).await?)
+      Pin::new(&mut *read).read(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
   }
 
-  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, AnyError> {
+  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let write = RcRef::map(self, |this| &this.write);
       let mut write = write.borrow_mut().await;
-      Ok(Pin::new(&mut *write).write(buf).await?)
+      Pin::new(&mut *write).write(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
@@ -1228,7 +1273,7 @@ impl UpgradeStream {
     self: Rc<Self>,
     buf1: &[u8],
     buf2: &[u8],
-  ) -> Result<usize, AnyError> {
+  ) -> Result<usize, std::io::Error> {
     let mut wr = RcRef::map(self, |r| &r.write).borrow_mut().await;
 
     let total = buf1.len() + buf2.len();
@@ -1281,9 +1326,12 @@ pub async fn op_raw_write_vectored(
   #[smi] rid: ResourceId,
   #[buffer] buf1: JsBuffer,
   #[buffer] buf2: JsBuffer,
-) -> Result<usize, AnyError> {
-  let resource: Rc<UpgradeStream> =
-    state.borrow().resource_table.get::<UpgradeStream>(rid)?;
+) -> Result<usize, HttpNextError> {
+  let resource: Rc<UpgradeStream> = state
+    .borrow()
+    .resource_table
+    .get::<UpgradeStream>(rid)
+    .map_err(HttpNextError::Resource)?;
   let nwritten = resource.write_vectored(&buf1, &buf2).await?;
   Ok(nwritten)
 }
diff --git a/ext/http/lib.rs b/ext/http/lib.rs
index 934f8a0024..6243804a14 100644
--- a/ext/http/lib.rs
+++ b/ext/http/lib.rs
@@ -6,8 +6,6 @@ use async_compression::Level;
 use base64::prelude::BASE64_STANDARD;
 use base64::Engine;
 use cache_control::CacheControl;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::futures::channel::mpsc;
 use deno_core::futures::channel::oneshot;
 use deno_core::futures::future::pending;
@@ -89,11 +87,14 @@ mod service;
 mod websocket_upgrade;
 
 use fly_accept_encoding::Encoding;
+pub use http_next::HttpNextError;
 pub use request_properties::DefaultHttpPropertyExtractor;
 pub use request_properties::HttpConnectionProperties;
 pub use request_properties::HttpListenProperties;
 pub use request_properties::HttpPropertyExtractor;
 pub use request_properties::HttpRequestProperties;
+pub use service::UpgradeUnavailableError;
+pub use websocket_upgrade::WebSocketUpgradeError;
 
 deno_core::extension!(
   deno_http,
@@ -134,6 +135,38 @@ deno_core::extension!(
   esm = ["00_serve.ts", "01_http.js", "02_websocket.ts"],
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error("{0}")]
+  HyperV014(#[source] Arc<hyper_v014::Error>),
+  #[error("{0}")]
+  InvalidHeaderName(#[from] hyper_v014::header::InvalidHeaderName),
+  #[error("{0}")]
+  InvalidHeaderValue(#[from] hyper_v014::header::InvalidHeaderValue),
+  #[error("{0}")]
+  Http(#[from] hyper_v014::http::Error),
+  #[error("response headers already sent")]
+  ResponseHeadersAlreadySent,
+  #[error("connection closed while sending response")]
+  ConnectionClosedWhileSendingResponse,
+  #[error("already in use")]
+  AlreadyInUse,
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error("no response headers")]
+  NoResponseHeaders,
+  #[error("response already completed")]
+  ResponseAlreadyCompleted,
+  #[error("cannot upgrade because request body was used")]
+  UpgradeBodyUsed,
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 pub enum HttpSocketAddr {
   IpSocket(std::net::SocketAddr),
   #[cfg(unix)]
@@ -216,7 +249,7 @@ impl HttpConnResource {
       String,
       String,
     )>,
-    AnyError,
+    HttpError,
   > {
     let fut = async {
       let (request_tx, request_rx) = oneshot::channel();
@@ -259,8 +292,8 @@ impl HttpConnResource {
   }
 
   /// A future that completes when this HTTP connection is closed or errors.
-  async fn closed(&self) -> Result<(), AnyError> {
-    self.closed_fut.clone().map_err(AnyError::from).await
+  async fn closed(&self) -> Result<(), HttpError> {
+    self.closed_fut.clone().map_err(HttpError::HyperV014).await
   }
 }
 
@@ -280,14 +313,13 @@ pub fn http_create_conn_resource<S, A>(
   io: S,
   addr: A,
   scheme: &'static str,
-) -> Result<ResourceId, AnyError>
+) -> ResourceId
 where
   S: AsyncRead + AsyncWrite + Unpin + Send + 'static,
   A: Into<HttpSocketAddr>,
 {
   let conn = HttpConnResource::new(io, scheme, addr.into());
-  let rid = state.resource_table.add(conn);
-  Ok(rid)
+  state.resource_table.add(conn)
 }
 
 /// An object that implements the `hyper::Service` trait, through which Hyper
@@ -423,7 +455,9 @@ impl Resource for HttpStreamReadResource {
             // safely call `await` on it without creating a race condition.
             Some(_) => match body.as_mut().next().await.unwrap() {
               Ok(chunk) => assert!(chunk.is_empty()),
-              Err(err) => break Err(AnyError::from(err)),
+              Err(err) => {
+                break Err(HttpError::HyperV014(Arc::new(err)).into())
+              }
             },
             None => break Ok(BufView::empty()),
           }
@@ -545,8 +579,12 @@ struct NextRequestResponse(
 async fn op_http_accept(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<NextRequestResponse>, AnyError> {
-  let conn = state.borrow().resource_table.get::<HttpConnResource>(rid)?;
+) -> Result<Option<NextRequestResponse>, HttpError> {
+  let conn = state
+    .borrow()
+    .resource_table
+    .get::<HttpConnResource>(rid)
+    .map_err(HttpError::Resource)?;
 
   match conn.accept().await {
     Ok(Some((read_stream, write_stream, method, url))) => {
@@ -657,11 +695,12 @@ async fn op_http_write_headers(
   #[smi] status: u16,
   #[serde] headers: Vec<(ByteString, ByteString)>,
   #[serde] data: Option<StringOrBuffer>,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let stream = state
     .borrow_mut()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
 
   // Track supported encoding
   let encoding = stream.accept_encoding;
@@ -708,14 +747,14 @@ async fn op_http_write_headers(
   let mut old_wr = RcRef::map(&stream, |r| &r.wr).borrow_mut().await;
   let response_tx = match replace(&mut *old_wr, new_wr) {
     HttpResponseWriter::Headers(response_tx) => response_tx,
-    _ => return Err(http_error("response headers already sent")),
+    _ => return Err(HttpError::ResponseHeadersAlreadySent),
   };
 
   match response_tx.send(body) {
     Ok(_) => Ok(()),
     Err(_) => {
       stream.conn.closed().await?;
-      Err(http_error("connection closed while sending response"))
+      Err(HttpError::ConnectionClosedWhileSendingResponse)
     }
   }
 }
@@ -725,11 +764,14 @@ async fn op_http_write_headers(
 fn op_http_headers(
   state: &mut OpState,
   #[smi] rid: u32,
-) -> Result<Vec<(ByteString, ByteString)>, AnyError> {
-  let stream = state.resource_table.get::<HttpStreamReadResource>(rid)?;
+) -> Result<Vec<(ByteString, ByteString)>, HttpError> {
+  let stream = state
+    .resource_table
+    .get::<HttpStreamReadResource>(rid)
+    .map_err(HttpError::Resource)?;
   let rd = RcRef::map(&stream, |r| &r.rd)
     .try_borrow()
-    .ok_or_else(|| http_error("already in use"))?;
+    .ok_or(HttpError::AlreadyInUse)?;
   match &*rd {
     HttpRequestReader::Headers(request) => Ok(req_headers(request.headers())),
     HttpRequestReader::Body(headers, _) => Ok(req_headers(headers)),
@@ -741,7 +783,7 @@ fn http_response(
   data: Option<StringOrBuffer>,
   compressing: bool,
   encoding: Encoding,
-) -> Result<(HttpResponseWriter, hyper_v014::Body), AnyError> {
+) -> Result<(HttpResponseWriter, hyper_v014::Body), HttpError> {
   // Gzip, after level 1, doesn't produce significant size difference.
   // This default matches nginx default gzip compression level (1):
   // https://nginx.org/en/docs/http/ngx_http_gzip_module.html#gzip_comp_level
@@ -878,25 +920,34 @@ async fn op_http_write_resource(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[smi] stream: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let http_stream = state
     .borrow()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut wr = RcRef::map(&http_stream, |r| &r.wr).borrow_mut().await;
-  let resource = state.borrow().resource_table.get_any(stream)?;
+  let resource = state
+    .borrow()
+    .resource_table
+    .get_any(stream)
+    .map_err(HttpError::Resource)?;
   loop {
     match *wr {
       HttpResponseWriter::Headers(_) => {
-        return Err(http_error("no response headers"))
+        return Err(HttpError::NoResponseHeaders)
       }
       HttpResponseWriter::Closed => {
-        return Err(http_error("response already completed"))
+        return Err(HttpError::ResponseAlreadyCompleted)
       }
       _ => {}
     };
 
-    let view = resource.clone().read(64 * 1024).await?; // 64KB
+    let view = resource
+      .clone()
+      .read(64 * 1024)
+      .await
+      .map_err(HttpError::Other)?; // 64KB
     if view.is_empty() {
       break;
     }
@@ -937,16 +988,17 @@ async fn op_http_write(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[buffer] buf: JsBuffer,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let stream = state
     .borrow()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut wr = RcRef::map(&stream, |r| &r.wr).borrow_mut().await;
 
   match &mut *wr {
-    HttpResponseWriter::Headers(_) => Err(http_error("no response headers")),
-    HttpResponseWriter::Closed => Err(http_error("response already completed")),
+    HttpResponseWriter::Headers(_) => Err(HttpError::NoResponseHeaders),
+    HttpResponseWriter::Closed => Err(HttpError::ResponseAlreadyCompleted),
     HttpResponseWriter::Body { writer, .. } => {
       let mut result = writer.write_all(&buf).await;
       if result.is_ok() {
@@ -961,7 +1013,7 @@ async fn op_http_write(
           stream.conn.closed().await?;
           // If there was no connection error, drop body_tx.
           *wr = HttpResponseWriter::Closed;
-          Err(http_error("response already completed"))
+          Err(HttpError::ResponseAlreadyCompleted)
         }
       }
     }
@@ -975,7 +1027,7 @@ async fn op_http_write(
           stream.conn.closed().await?;
           // If there was no connection error, drop body_tx.
           *wr = HttpResponseWriter::Closed;
-          Err(http_error("response already completed"))
+          Err(HttpError::ResponseAlreadyCompleted)
         }
       }
     }
@@ -989,11 +1041,12 @@ async fn op_http_write(
 async fn op_http_shutdown(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), HttpError> {
   let stream = state
     .borrow()
     .resource_table
-    .get::<HttpStreamWriteResource>(rid)?;
+    .get::<HttpStreamWriteResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut wr = RcRef::map(&stream, |r| &r.wr).borrow_mut().await;
   let wr = take(&mut *wr);
   match wr {
@@ -1022,14 +1075,12 @@ async fn op_http_shutdown(
 
 #[op2]
 #[string]
-fn op_http_websocket_accept_header(
-  #[string] key: String,
-) -> Result<String, AnyError> {
+fn op_http_websocket_accept_header(#[string] key: String) -> String {
   let digest = ring::digest::digest(
     &ring::digest::SHA1_FOR_LEGACY_USE_ONLY,
     format!("{key}258EAFA5-E914-47DA-95CA-C5AB0DC85B11").as_bytes(),
   );
-  Ok(BASE64_STANDARD.encode(digest))
+  BASE64_STANDARD.encode(digest)
 }
 
 #[op2(async)]
@@ -1037,25 +1088,29 @@ fn op_http_websocket_accept_header(
 async fn op_http_upgrade_websocket(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpError> {
   let stream = state
     .borrow_mut()
     .resource_table
-    .get::<HttpStreamReadResource>(rid)?;
+    .get::<HttpStreamReadResource>(rid)
+    .map_err(HttpError::Resource)?;
   let mut rd = RcRef::map(&stream, |r| &r.rd).borrow_mut().await;
 
   let request = match &mut *rd {
     HttpRequestReader::Headers(request) => request,
-    _ => {
-      return Err(http_error("cannot upgrade because request body was used"))
-    }
+    _ => return Err(HttpError::UpgradeBodyUsed),
   };
 
-  let (transport, bytes) =
-    extract_network_stream(hyper_v014::upgrade::on(request).await?);
-  let ws_rid =
-    ws_create_server_stream(&mut state.borrow_mut(), transport, bytes)?;
-  Ok(ws_rid)
+  let (transport, bytes) = extract_network_stream(
+    hyper_v014::upgrade::on(request)
+      .await
+      .map_err(|err| HttpError::HyperV014(Arc::new(err)))?,
+  );
+  Ok(ws_create_server_stream(
+    &mut state.borrow_mut(),
+    transport,
+    bytes,
+  ))
 }
 
 // Needed so hyper can use non Send futures
@@ -1082,10 +1137,6 @@ where
   }
 }
 
-fn http_error(message: &'static str) -> AnyError {
-  custom_error("Http", message)
-}
-
 /// Filters out the ever-surprising 'shutdown ENOTCONN' errors.
 fn filter_enotconn(
   result: Result<(), hyper_v014::Error>,
diff --git a/ext/http/request_body.rs b/ext/http/request_body.rs
index 45df12457c..f1c3f358ea 100644
--- a/ext/http/request_body.rs
+++ b/ext/http/request_body.rs
@@ -1,9 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 use bytes::Bytes;
-use deno_core::error::AnyError;
 use deno_core::futures::stream::Peekable;
 use deno_core::futures::Stream;
 use deno_core::futures::StreamExt;
+use deno_core::futures::TryFutureExt;
 use deno_core::AsyncRefCell;
 use deno_core::AsyncResult;
 use deno_core::BufView;
@@ -22,7 +22,7 @@ use std::task::Poll;
 struct ReadFuture(Incoming);
 
 impl Stream for ReadFuture {
-  type Item = Result<Bytes, AnyError>;
+  type Item = Result<Bytes, hyper::Error>;
 
   fn poll_next(
     self: Pin<&mut Self>,
@@ -37,13 +37,13 @@ impl Stream for ReadFuture {
           if let Ok(data) = frame.into_data() {
             // Ensure that we never yield an empty frame
             if !data.is_empty() {
-              break Poll::Ready(Some(Ok::<_, AnyError>(data)));
+              break Poll::Ready(Some(Ok(data)));
             }
           }
           // Loop again so we don't lose the waker
           continue;
         }
-        Some(Err(e)) => Poll::Ready(Some(Err(e.into()))),
+        Some(Err(e)) => Poll::Ready(Some(Err(e))),
         None => Poll::Ready(None),
       };
     }
@@ -58,7 +58,7 @@ impl HttpRequestBody {
     Self(AsyncRefCell::new(ReadFuture(body).peekable()), size_hint)
   }
 
-  async fn read(self: Rc<Self>, limit: usize) -> Result<BufView, AnyError> {
+  async fn read(self: Rc<Self>, limit: usize) -> Result<BufView, hyper::Error> {
     let peekable = RcRef::map(self, |this| &this.0);
     let mut peekable = peekable.borrow_mut().await;
     match Pin::new(&mut *peekable).peek_mut().await {
@@ -82,7 +82,7 @@ impl Resource for HttpRequestBody {
   }
 
   fn read(self: Rc<Self>, limit: usize) -> AsyncResult<BufView> {
-    Box::pin(HttpRequestBody::read(self, limit))
+    Box::pin(HttpRequestBody::read(self, limit).map_err(Into::into))
   }
 
   fn size_hint(&self) -> (u64, Option<u64>) {
diff --git a/ext/http/request_properties.rs b/ext/http/request_properties.rs
index 1422c7417d..39d35a79f1 100644
--- a/ext/http/request_properties.rs
+++ b/ext/http/request_properties.rs
@@ -34,8 +34,8 @@ pub struct HttpConnectionProperties {
   pub stream_type: NetworkStreamType,
 }
 
-pub struct HttpRequestProperties {
-  pub authority: Option<String>,
+pub struct HttpRequestProperties<'a> {
+  pub authority: Option<Cow<'a, str>>,
 }
 
 /// Pluggable trait to determine listen, connection and request properties
@@ -84,11 +84,11 @@ pub trait HttpPropertyExtractor {
   ) -> NetworkStream;
 
   /// Determines the request properties.
-  fn request_properties(
-    connection_properties: &HttpConnectionProperties,
-    uri: &Uri,
-    headers: &HeaderMap,
-  ) -> HttpRequestProperties;
+  fn request_properties<'a>(
+    connection_properties: &'a HttpConnectionProperties,
+    uri: &'a Uri,
+    headers: &'a HeaderMap,
+  ) -> HttpRequestProperties<'a>;
 }
 
 pub struct DefaultHttpPropertyExtractor {}
@@ -180,18 +180,17 @@ impl HttpPropertyExtractor for DefaultHttpPropertyExtractor {
     }
   }
 
-  fn request_properties(
-    connection_properties: &HttpConnectionProperties,
-    uri: &Uri,
-    headers: &HeaderMap,
-  ) -> HttpRequestProperties {
+  fn request_properties<'a>(
+    connection_properties: &'a HttpConnectionProperties,
+    uri: &'a Uri,
+    headers: &'a HeaderMap,
+  ) -> HttpRequestProperties<'a> {
     let authority = req_host(
       uri,
       headers,
       connection_properties.stream_type,
       connection_properties.local_port.unwrap_or_default(),
-    )
-    .map(|s| s.into_owned());
+    );
 
     HttpRequestProperties { authority }
   }
diff --git a/ext/http/service.rs b/ext/http/service.rs
index 787e9babf8..75f93d77c2 100644
--- a/ext/http/service.rs
+++ b/ext/http/service.rs
@@ -2,7 +2,6 @@
 use crate::request_properties::HttpConnectionProperties;
 use crate::response_body::ResponseBytesInner;
 use crate::response_body::ResponseStreamResult;
-use deno_core::error::AnyError;
 use deno_core::futures::ready;
 use deno_core::BufView;
 use deno_core::OpState;
@@ -206,6 +205,10 @@ pub(crate) async fn handle_request(
   Ok(response)
 }
 
+#[derive(Debug, thiserror::Error)]
+#[error("upgrade unavailable")]
+pub struct UpgradeUnavailableError;
+
 struct HttpRecordInner {
   server_state: SignallingRc<HttpServerState>,
   request_info: HttpConnectionProperties,
@@ -344,14 +347,14 @@ impl HttpRecord {
   }
 
   /// Perform the Hyper upgrade on this record.
-  pub fn upgrade(&self) -> Result<OnUpgrade, AnyError> {
+  pub fn upgrade(&self) -> Result<OnUpgrade, UpgradeUnavailableError> {
     // Manually perform the upgrade. We're peeking into hyper's underlying machinery here a bit
     self
       .self_mut()
       .request_parts
       .extensions
       .remove::<OnUpgrade>()
-      .ok_or_else(|| AnyError::msg("upgrade unavailable"))
+      .ok_or(UpgradeUnavailableError)
   }
 
   /// Take the Hyper body from this record.
@@ -515,7 +518,7 @@ pub struct HttpRecordResponse(ManuallyDrop<Rc<HttpRecord>>);
 
 impl Body for HttpRecordResponse {
   type Data = BufView;
-  type Error = AnyError;
+  type Error = deno_core::error::AnyError;
 
   fn poll_frame(
     self: Pin<&mut Self>,
@@ -640,7 +643,7 @@ mod tests {
   }
 
   #[tokio::test]
-  async fn test_handle_request() -> Result<(), AnyError> {
+  async fn test_handle_request() -> Result<(), deno_core::error::AnyError> {
     let (tx, mut rx) = tokio::sync::mpsc::channel(10);
     let server_state = HttpServerState::new();
     let server_state_check = server_state.clone();
diff --git a/ext/http/websocket_upgrade.rs b/ext/http/websocket_upgrade.rs
index 4dead767a3..af9504717e 100644
--- a/ext/http/websocket_upgrade.rs
+++ b/ext/http/websocket_upgrade.rs
@@ -4,7 +4,6 @@ use std::marker::PhantomData;
 
 use bytes::Bytes;
 use bytes::BytesMut;
-use deno_core::error::AnyError;
 use httparse::Status;
 use hyper::header::HeaderName;
 use hyper::header::HeaderValue;
@@ -13,12 +12,30 @@ use memmem::Searcher;
 use memmem::TwoWaySearcher;
 use once_cell::sync::OnceCell;
 
-use crate::http_error;
+#[derive(Debug, thiserror::Error)]
+pub enum WebSocketUpgradeError {
+  #[error("invalid headers")]
+  InvalidHeaders,
+  #[error("{0}")]
+  HttpParse(#[from] httparse::Error),
+  #[error("{0}")]
+  Http(#[from] http::Error),
+  #[error("{0}")]
+  Utf8(#[from] std::str::Utf8Error),
+  #[error("{0}")]
+  InvalidHeaderName(#[from] http::header::InvalidHeaderName),
+  #[error("{0}")]
+  InvalidHeaderValue(#[from] http::header::InvalidHeaderValue),
+  #[error("invalid HTTP status line")]
+  InvalidHttpStatusLine,
+  #[error("attempted to write to completed upgrade buffer")]
+  UpgradeBufferAlreadyCompleted,
+}
 
 /// Given a buffer that ends in `\n\n` or `\r\n\r\n`, returns a parsed [`Request<Body>`].
 fn parse_response<T: Default>(
   header_bytes: &[u8],
-) -> Result<(usize, Response<T>), AnyError> {
+) -> Result<(usize, Response<T>), WebSocketUpgradeError> {
   let mut headers = [httparse::EMPTY_HEADER; 16];
   let status = httparse::parse_headers(header_bytes, &mut headers)?;
   match status {
@@ -32,7 +49,7 @@ fn parse_response<T: Default>(
       }
       Ok((index, resp))
     }
-    _ => Err(http_error("invalid headers")),
+    _ => Err(WebSocketUpgradeError::InvalidHeaders),
   }
 }
 
@@ -69,11 +86,14 @@ pub struct WebSocketUpgrade<T: Default> {
 impl<T: Default> WebSocketUpgrade<T> {
   /// Ensures that the status line starts with "HTTP/1.1 101 " which matches all of the node.js
   /// WebSocket libraries that are known. We don't care about the trailing status text.
-  fn validate_status(&self, status: &[u8]) -> Result<(), AnyError> {
+  fn validate_status(
+    &self,
+    status: &[u8],
+  ) -> Result<(), WebSocketUpgradeError> {
     if status.starts_with(b"HTTP/1.1 101 ") {
       Ok(())
     } else {
-      Err(http_error("invalid HTTP status line"))
+      Err(WebSocketUpgradeError::InvalidHttpStatusLine)
     }
   }
 
@@ -82,7 +102,7 @@ impl<T: Default> WebSocketUpgrade<T> {
   pub fn write(
     &mut self,
     bytes: &[u8],
-  ) -> Result<Option<(Response<T>, Bytes)>, AnyError> {
+  ) -> Result<Option<(Response<T>, Bytes)>, WebSocketUpgradeError> {
     use WebSocketUpgradeState::*;
 
     match self.state {
@@ -142,9 +162,7 @@ impl<T: Default> WebSocketUpgrade<T> {
           Ok(None)
         }
       }
-      Complete => {
-        Err(http_error("attempted to write to completed upgrade buffer"))
-      }
+      Complete => Err(WebSocketUpgradeError::UpgradeBufferAlreadyCompleted),
     }
   }
 }
@@ -157,8 +175,8 @@ mod tests {
   type ExpectedResponseAndHead = Option<(Response<Body>, &'static [u8])>;
 
   fn assert_response(
-    result: Result<Option<(Response<Body>, Bytes)>, AnyError>,
-    expected: Result<ExpectedResponseAndHead, &'static str>,
+    result: Result<Option<(Response<Body>, Bytes)>, WebSocketUpgradeError>,
+    expected: Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
     chunk_info: Option<(usize, usize)>,
   ) {
     let formatted = format!("{result:?}");
@@ -189,8 +207,8 @@ mod tests {
         "Expected Ok(None), was {formatted}",
       ),
       Err(e) => assert_eq!(
-        e,
-        result.err().map(|e| format!("{e:?}")).unwrap_or_default(),
+        format!("{e:?}"),
+        format!("{:?}", result.unwrap_err()),
         "Expected error, was {formatted}",
       ),
     }
@@ -198,7 +216,7 @@ mod tests {
 
   fn validate_upgrade_all_at_once(
     s: &str,
-    expected: Result<ExpectedResponseAndHead, &'static str>,
+    expected: Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
   ) {
     let mut upgrade = WebSocketUpgrade::default();
     let res = upgrade.write(s.as_bytes());
@@ -209,7 +227,7 @@ mod tests {
   fn validate_upgrade_chunks(
     s: &str,
     size: usize,
-    expected: Result<ExpectedResponseAndHead, &'static str>,
+    expected: Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
   ) {
     let chunk_info = Some((s.as_bytes().len(), size));
     let mut upgrade = WebSocketUpgrade::default();
@@ -226,7 +244,7 @@ mod tests {
 
   fn validate_upgrade(
     s: &str,
-    expected: fn() -> Result<ExpectedResponseAndHead, &'static str>,
+    expected: fn() -> Result<ExpectedResponseAndHead, WebSocketUpgradeError>,
   ) {
     validate_upgrade_all_at_once(s, expected());
     validate_upgrade_chunks(s, 1, expected());
@@ -315,7 +333,7 @@ mod tests {
   #[test]
   fn upgrade_invalid_status() {
     validate_upgrade("HTTP/1.1 200 OK\nConnection: Upgrade\n\n", || {
-      Err("invalid HTTP status line")
+      Err(WebSocketUpgradeError::InvalidHttpStatusLine)
     });
   }
 
@@ -327,7 +345,11 @@ mod tests {
       .join("\n");
     validate_upgrade(
       &format!("HTTP/1.1 101 Switching Protocols\n{headers}\n\n"),
-      || Err("too many headers"),
+      || {
+        Err(WebSocketUpgradeError::HttpParse(
+          httparse::Error::TooManyHeaders,
+        ))
+      },
     );
   }
 }
diff --git a/ext/io/Cargo.toml b/ext/io/Cargo.toml
index d45834a8fe..7e858d298c 100644
--- a/ext/io/Cargo.toml
+++ b/ext/io/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_io"
-version = "0.81.0"
+version = "0.85.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/io/bi_pipe.rs b/ext/io/bi_pipe.rs
index 402e383ac9..3492e2f441 100644
--- a/ext/io/bi_pipe.rs
+++ b/ext/io/bi_pipe.rs
@@ -2,7 +2,6 @@
 
 use std::rc::Rc;
 
-use deno_core::error::AnyError;
 use deno_core::AsyncRefCell;
 use deno_core::AsyncResult;
 use deno_core::CancelHandle;
@@ -71,13 +70,16 @@ impl BiPipeResource {
   pub async fn read(
     self: Rc<Self>,
     data: &mut [u8],
-  ) -> Result<usize, AnyError> {
+  ) -> Result<usize, std::io::Error> {
     let mut rd = RcRef::map(&self, |r| &r.read_half).borrow_mut().await;
     let cancel_handle = RcRef::map(&self, |r| &r.cancel);
-    Ok(rd.read(data).try_or_cancel(cancel_handle).await?)
+    rd.read(data).try_or_cancel(cancel_handle).await
   }
 
-  pub async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, AnyError> {
+  pub async fn write(
+    self: Rc<Self>,
+    data: &[u8],
+  ) -> Result<usize, std::io::Error> {
     let mut wr = RcRef::map(self, |r| &r.write_half).borrow_mut().await;
     let nwritten = wr.write(data).await?;
     wr.flush().await?;
@@ -181,9 +183,10 @@ fn from_raw(
 ) -> Result<(BiPipeRead, BiPipeWrite), std::io::Error> {
   use std::os::fd::FromRawFd;
   // Safety: The fd is part of a pair of connected sockets
-  let unix_stream = tokio::net::UnixStream::from_std(unsafe {
-    std::os::unix::net::UnixStream::from_raw_fd(stream)
-  })?;
+  let unix_stream =
+    unsafe { std::os::unix::net::UnixStream::from_raw_fd(stream) };
+  unix_stream.set_nonblocking(true)?;
+  let unix_stream = tokio::net::UnixStream::from_std(unix_stream)?;
   let (read, write) = unix_stream.into_split();
   Ok((BiPipeRead { inner: read }, BiPipeWrite { inner: write }))
 }
@@ -270,15 +273,15 @@ impl_async_write!(for BiPipe -> self.write_end);
 
 /// Creates both sides of a bidirectional pipe, returning the raw
 /// handles to the underlying OS resources.
-pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError>
-{
+pub fn bi_pipe_pair_raw(
+) -> Result<(RawBiPipeHandle, RawBiPipeHandle), std::io::Error> {
   #[cfg(unix)]
   {
     // SockFlag is broken on macOS
     // https://github.com/nix-rust/nix/issues/861
     let mut fds = [-1, -1];
     #[cfg(not(target_os = "macos"))]
-    let flags = libc::SOCK_CLOEXEC | libc::SOCK_NONBLOCK;
+    let flags = libc::SOCK_CLOEXEC;
 
     #[cfg(target_os = "macos")]
     let flags = 0;
@@ -293,19 +296,19 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
       )
     };
     if ret != 0 {
-      return Err(std::io::Error::last_os_error().into());
+      return Err(std::io::Error::last_os_error());
     }
 
     if cfg!(target_os = "macos") {
       let fcntl = |fd: i32, flag: libc::c_int| -> Result<(), std::io::Error> {
         // SAFETY: libc call, fd is valid
-        let flags = unsafe { libc::fcntl(fd, libc::F_GETFL) };
+        let flags = unsafe { libc::fcntl(fd, libc::F_GETFD) };
 
         if flags == -1 {
           return Err(fail(fds));
         }
         // SAFETY: libc call, fd is valid
-        let ret = unsafe { libc::fcntl(fd, libc::F_SETFL, flags | flag) };
+        let ret = unsafe { libc::fcntl(fd, libc::F_SETFD, flags | flag) };
         if ret == -1 {
           return Err(fail(fds));
         }
@@ -321,13 +324,9 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
         std::io::Error::last_os_error()
       }
 
-      // SOCK_NONBLOCK is not supported on macOS.
-      (fcntl)(fds[0], libc::O_NONBLOCK)?;
-      (fcntl)(fds[1], libc::O_NONBLOCK)?;
-
       // SOCK_CLOEXEC is not supported on macOS.
-      (fcntl)(fds[0], libc::FD_CLOEXEC)?;
-      (fcntl)(fds[1], libc::FD_CLOEXEC)?;
+      fcntl(fds[0], libc::FD_CLOEXEC)?;
+      fcntl(fds[1], libc::FD_CLOEXEC)?;
     }
 
     let fd1 = fds[0];
@@ -389,7 +388,7 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
             continue;
           }
 
-          return Err(err.into());
+          return Err(err);
         }
 
         break (path, hd1);
@@ -411,7 +410,7 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
         0,
       );
       if hd2 == INVALID_HANDLE_VALUE {
-        return Err(io::Error::last_os_error().into());
+        return Err(io::Error::last_os_error());
       }
 
       // Will not block because we have create the pair.
@@ -419,7 +418,7 @@ pub fn bi_pipe_pair_raw() -> Result<(RawBiPipeHandle, RawBiPipeHandle), AnyError
         let err = std::io::Error::last_os_error();
         if err.raw_os_error() != Some(ERROR_PIPE_CONNECTED as i32) {
           CloseHandle(hd2);
-          return Err(err.into());
+          return Err(err);
         }
       }
 
diff --git a/ext/io/fs.rs b/ext/io/fs.rs
index 3798c1429d..8854265209 100644
--- a/ext/io/fs.rs
+++ b/ext/io/fs.rs
@@ -1,15 +1,12 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use std::borrow::Cow;
+use std::fmt::Formatter;
 use std::io;
 use std::rc::Rc;
 use std::time::SystemTime;
 use std::time::UNIX_EPOCH;
 
-use deno_core::error::custom_error;
-use deno_core::error::not_supported;
-use deno_core::error::resource_unavailable;
-use deno_core::error::AnyError;
 use deno_core::BufMutView;
 use deno_core::BufView;
 use deno_core::OpState;
@@ -25,6 +22,21 @@ pub enum FsError {
   NotCapable(&'static str),
 }
 
+impl std::fmt::Display for FsError {
+  fn fmt(&self, f: &mut Formatter<'_>) -> std::fmt::Result {
+    match self {
+      FsError::Io(err) => std::fmt::Display::fmt(err, f),
+      FsError::FileBusy => f.write_str("file busy"),
+      FsError::NotSupported => f.write_str("not supported"),
+      FsError::NotCapable(err) => {
+        f.write_str(&format!("requires {err} access"))
+      }
+    }
+  }
+}
+
+impl std::error::Error for FsError {}
+
 impl FsError {
   pub fn kind(&self) -> io::ErrorKind {
     match self {
@@ -59,19 +71,6 @@ impl From<io::ErrorKind> for FsError {
   }
 }
 
-impl From<FsError> for AnyError {
-  fn from(err: FsError) -> Self {
-    match err {
-      FsError::Io(err) => AnyError::from(err),
-      FsError::FileBusy => resource_unavailable(),
-      FsError::NotSupported => not_supported(),
-      FsError::NotCapable(err) => {
-        custom_error("NotCapable", format!("permission denied: {err}"))
-      }
-    }
-  }
-}
-
 impl From<JoinError> for FsError {
   fn from(err: JoinError) -> Self {
     if err.is_cancelled() {
@@ -266,9 +265,9 @@ impl FileResource {
     state: &OpState,
     rid: ResourceId,
     f: F,
-  ) -> Result<R, AnyError>
+  ) -> Result<R, deno_core::error::AnyError>
   where
-    F: FnOnce(Rc<FileResource>) -> Result<R, AnyError>,
+    F: FnOnce(Rc<FileResource>) -> Result<R, deno_core::error::AnyError>,
   {
     let resource = state.resource_table.get::<FileResource>(rid)?;
     f(resource)
@@ -277,7 +276,7 @@ impl FileResource {
   pub fn get_file(
     state: &OpState,
     rid: ResourceId,
-  ) -> Result<Rc<dyn File>, AnyError> {
+  ) -> Result<Rc<dyn File>, deno_core::error::AnyError> {
     let resource = state.resource_table.get::<FileResource>(rid)?;
     Ok(resource.file())
   }
@@ -286,9 +285,9 @@ impl FileResource {
     state: &OpState,
     rid: ResourceId,
     f: F,
-  ) -> Result<R, AnyError>
+  ) -> Result<R, deno_core::error::AnyError>
   where
-    F: FnOnce(Rc<dyn File>) -> Result<R, AnyError>,
+    F: FnOnce(Rc<dyn File>) -> Result<R, deno_core::error::AnyError>,
   {
     Self::with_resource(state, rid, |r| f(r.file.clone()))
   }
@@ -303,10 +302,7 @@ impl deno_core::Resource for FileResource {
     Cow::Borrowed(&self.name)
   }
 
-  fn read(
-    self: Rc<Self>,
-    limit: usize,
-  ) -> deno_core::AsyncResult<deno_core::BufView> {
+  fn read(self: Rc<Self>, limit: usize) -> deno_core::AsyncResult<BufView> {
     Box::pin(async move {
       self
         .file
@@ -319,8 +315,8 @@ impl deno_core::Resource for FileResource {
 
   fn read_byob(
     self: Rc<Self>,
-    buf: deno_core::BufMutView,
-  ) -> deno_core::AsyncResult<(usize, deno_core::BufMutView)> {
+    buf: BufMutView,
+  ) -> deno_core::AsyncResult<(usize, BufMutView)> {
     Box::pin(async move {
       self
         .file
@@ -333,17 +329,14 @@ impl deno_core::Resource for FileResource {
 
   fn write(
     self: Rc<Self>,
-    buf: deno_core::BufView,
+    buf: BufView,
   ) -> deno_core::AsyncResult<deno_core::WriteOutcome> {
     Box::pin(async move {
       self.file.clone().write(buf).await.map_err(|err| err.into())
     })
   }
 
-  fn write_all(
-    self: Rc<Self>,
-    buf: deno_core::BufView,
-  ) -> deno_core::AsyncResult<()> {
+  fn write_all(self: Rc<Self>, buf: BufView) -> deno_core::AsyncResult<()> {
     Box::pin(async move {
       self
         .file
diff --git a/ext/io/lib.rs b/ext/io/lib.rs
index a07d64ae37..5d183aa464 100644
--- a/ext/io/lib.rs
+++ b/ext/io/lib.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::unsync::spawn_blocking;
 use deno_core::unsync::TaskQueue;
@@ -48,6 +47,7 @@ use winapi::um::processenv::GetStdHandle;
 #[cfg(windows)]
 use winapi::um::winbase;
 
+use deno_core::futures::TryFutureExt;
 #[cfg(windows)]
 use parking_lot::Condvar;
 #[cfg(windows)]
@@ -348,13 +348,13 @@ where
     RcRef::map(self, |r| &r.stream).borrow_mut()
   }
 
-  async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, AnyError> {
+  async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, io::Error> {
     let mut stream = self.borrow_mut().await;
     let nwritten = stream.write(data).await?;
     Ok(nwritten)
   }
 
-  async fn shutdown(self: Rc<Self>) -> Result<(), AnyError> {
+  async fn shutdown(self: Rc<Self>) -> Result<(), io::Error> {
     let mut stream = self.borrow_mut().await;
     stream.shutdown().await?;
     Ok(())
@@ -396,7 +396,7 @@ where
     self.cancel_handle.cancel()
   }
 
-  async fn read(self: Rc<Self>, data: &mut [u8]) -> Result<usize, AnyError> {
+  async fn read(self: Rc<Self>, data: &mut [u8]) -> Result<usize, io::Error> {
     let mut rd = self.borrow_mut().await;
     let nread = rd.read(data).try_or_cancel(self.cancel_handle()).await?;
     Ok(nread)
@@ -417,7 +417,7 @@ impl Resource for ChildStdinResource {
   deno_core::impl_writable!();
 
   fn shutdown(self: Rc<Self>) -> AsyncResult<()> {
-    Box::pin(self.shutdown())
+    Box::pin(self.shutdown().map_err(|e| e.into()))
   }
 }
 
@@ -1010,7 +1010,7 @@ pub fn op_print(
   state: &mut OpState,
   #[string] msg: &str,
   is_err: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let rid = if is_err { 2 } else { 1 };
   FileResource::with_file(state, rid, move |file| {
     Ok(file.write_all_sync(msg.as_bytes())?)
diff --git a/ext/kv/Cargo.toml b/ext/kv/Cargo.toml
index 14c3514ffd..bbd2349011 100644
--- a/ext/kv/Cargo.toml
+++ b/ext/kv/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_kv"
-version = "0.79.0"
+version = "0.83.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -36,6 +36,7 @@ prost.workspace = true
 rand.workspace = true
 rusqlite.workspace = true
 serde.workspace = true
+thiserror.workspace = true
 url.workspace = true
 
 [build-dependencies]
diff --git a/ext/kv/lib.rs b/ext/kv/lib.rs
index 13e4f1662f..a4ccfe3d63 100644
--- a/ext/kv/lib.rs
+++ b/ext/kv/lib.rs
@@ -12,15 +12,11 @@ use std::num::NonZeroU32;
 use std::rc::Rc;
 use std::time::Duration;
 
-use anyhow::bail;
 use base64::prelude::BASE64_URL_SAFE;
 use base64::Engine;
 use chrono::DateTime;
 use chrono::Utc;
-use deno_core::anyhow::Context;
 use deno_core::error::get_custom_error_class;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::StreamExt;
 use deno_core::op2;
 use deno_core::serde_v8::AnyValue;
@@ -118,12 +114,72 @@ impl Resource for DatabaseWatcherResource {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum KvError {
+  #[error(transparent)]
+  DatabaseHandler(deno_core::error::AnyError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("Too many ranges (max {0})")]
+  TooManyRanges(usize),
+  #[error("Too many entries (max {0})")]
+  TooManyEntries(usize),
+  #[error("Too many checks (max {0})")]
+  TooManyChecks(usize),
+  #[error("Too many mutations (max {0})")]
+  TooManyMutations(usize),
+  #[error("Too many keys (max {0})")]
+  TooManyKeys(usize),
+  #[error("limit must be greater than 0")]
+  InvalidLimit,
+  #[error("Invalid boundary key")]
+  InvalidBoundaryKey,
+  #[error("Key too large for read (max {0} bytes)")]
+  KeyTooLargeToRead(usize),
+  #[error("Key too large for write (max {0} bytes)")]
+  KeyTooLargeToWrite(usize),
+  #[error("Total mutation size too large (max {0} bytes)")]
+  TotalMutationTooLarge(usize),
+  #[error("Total key size too large (max {0} bytes)")]
+  TotalKeyTooLarge(usize),
+  #[error(transparent)]
+  Kv(deno_core::error::AnyError),
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  #[error("Queue message not found")]
+  QueueMessageNotFound,
+  #[error("Start key is not in the keyspace defined by prefix")]
+  StartKeyNotInKeyspace,
+  #[error("End key is not in the keyspace defined by prefix")]
+  EndKeyNotInKeyspace,
+  #[error("Start key is greater than end key")]
+  StartKeyGreaterThanEndKey,
+  #[error("Invalid check")]
+  InvalidCheck(#[source] KvCheckError),
+  #[error("Invalid mutation")]
+  InvalidMutation(#[source] KvMutationError),
+  #[error("Invalid enqueue")]
+  InvalidEnqueue(#[source] std::io::Error),
+  #[error("key cannot be empty")]
+  EmptyKey, // TypeError
+  #[error("Value too large (max {0} bytes)")]
+  ValueTooLarge(usize), // TypeError
+  #[error("enqueue payload too large (max {0} bytes)")]
+  EnqueuePayloadTooLarge(usize), // TypeError
+  #[error("invalid cursor")]
+  InvalidCursor,
+  #[error("cursor out of bounds")]
+  CursorOutOfBounds,
+  #[error("Invalid range")]
+  InvalidRange,
+}
+
 #[op2(async)]
 #[smi]
 async fn op_kv_database_open<DBH>(
   state: Rc<RefCell<OpState>>,
   #[string] path: Option<String>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
@@ -134,7 +190,10 @@ where
       .check_or_exit(UNSTABLE_FEATURE_NAME, "Deno.openKv");
     state.borrow::<Rc<DBH>>().clone()
   };
-  let db = handler.open(state.clone(), path).await?;
+  let db = handler
+    .open(state.clone(), path)
+    .await
+    .map_err(KvError::DatabaseHandler)?;
   let rid = state.borrow_mut().resource_table.add(DatabaseResource {
     db,
     cancel_handle: CancelHandle::new_rc(),
@@ -184,8 +243,8 @@ enum ToV8Value {
 }
 
 impl TryFrom<FromV8Value> for KvValue {
-  type Error = AnyError;
-  fn try_from(value: FromV8Value) -> Result<Self, AnyError> {
+  type Error = num_bigint::TryFromBigIntError<num_bigint::BigInt>;
+  fn try_from(value: FromV8Value) -> Result<Self, Self::Error> {
     Ok(match value {
       FromV8Value::V8(buf) => KvValue::V8(buf.to_vec()),
       FromV8Value::Bytes(buf) => KvValue::Bytes(buf.to_vec()),
@@ -214,8 +273,8 @@ struct ToV8KvEntry {
 }
 
 impl TryFrom<KvEntry> for ToV8KvEntry {
-  type Error = AnyError;
-  fn try_from(entry: KvEntry) -> Result<Self, AnyError> {
+  type Error = std::io::Error;
+  fn try_from(entry: KvEntry) -> Result<Self, Self::Error> {
     Ok(ToV8KvEntry {
       key: decode_key(&entry.key)?
         .0
@@ -261,14 +320,16 @@ async fn op_kv_snapshot_read<DBH>(
   #[smi] rid: ResourceId,
   #[serde] ranges: Vec<SnapshotReadRange>,
   #[serde] consistency: V8Consistency,
-) -> Result<Vec<Vec<ToV8KvEntry>>, AnyError>
+) -> Result<Vec<Vec<ToV8KvEntry>>, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
   let db = {
     let state = state.borrow();
-    let resource =
-      state.resource_table.get::<DatabaseResource<DBH::DB>>(rid)?;
+    let resource = state
+      .resource_table
+      .get::<DatabaseResource<DBH::DB>>(rid)
+      .map_err(KvError::Resource)?;
     resource.db.clone()
   };
 
@@ -278,10 +339,7 @@ where
   };
 
   if ranges.len() > config.max_read_ranges {
-    return Err(type_error(format!(
-      "Too many ranges (max {})",
-      config.max_read_ranges
-    )));
+    return Err(KvError::TooManyRanges(config.max_read_ranges));
   }
 
   let mut total_entries = 0usize;
@@ -300,33 +358,32 @@ where
       Ok(ReadRange {
         start,
         end,
-        limit: NonZeroU32::new(limit)
-          .with_context(|| "limit must be greater than 0")?,
+        limit: NonZeroU32::new(limit).ok_or(KvError::InvalidLimit)?,
         reverse,
       })
     })
-    .collect::<Result<Vec<_>, AnyError>>()?;
+    .collect::<Result<Vec<_>, KvError>>()?;
 
   if total_entries > config.max_read_entries {
-    return Err(type_error(format!(
-      "Too many entries (max {})",
-      config.max_read_entries
-    )));
+    return Err(KvError::TooManyEntries(config.max_read_entries));
   }
 
   let opts = SnapshotReadOptions {
     consistency: consistency.into(),
   };
-  let output_ranges = db.snapshot_read(read_ranges, opts).await?;
+  let output_ranges = db
+    .snapshot_read(read_ranges, opts)
+    .await
+    .map_err(KvError::Kv)?;
   let output_ranges = output_ranges
     .into_iter()
     .map(|x| {
       x.entries
         .into_iter()
         .map(TryInto::try_into)
-        .collect::<Result<Vec<_>, AnyError>>()
+        .collect::<Result<Vec<_>, std::io::Error>>()
     })
-    .collect::<Result<Vec<_>, AnyError>>()?;
+    .collect::<Result<Vec<_>, std::io::Error>>()?;
   Ok(output_ranges)
 }
 
@@ -345,7 +402,7 @@ impl<QMH: QueueMessageHandle + 'static> Resource for QueueMessageResource<QMH> {
 async fn op_kv_dequeue_next_message<DBH>(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<(ToJsBuffer, ResourceId)>, AnyError>
+) -> Result<Option<(ToJsBuffer, ResourceId)>, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
@@ -358,17 +415,19 @@ where
           if get_custom_error_class(&err) == Some("BadResource") {
             return Ok(None);
           } else {
-            return Err(err);
+            return Err(KvError::Resource(err));
           }
         }
       };
     resource.db.clone()
   };
 
-  let Some(mut handle) = db.dequeue_next_message().await? else {
+  let Some(mut handle) =
+    db.dequeue_next_message().await.map_err(KvError::Kv)?
+  else {
     return Ok(None);
   };
-  let payload = handle.take_payload().await?.into();
+  let payload = handle.take_payload().await.map_err(KvError::Kv)?.into();
   let handle_rid = {
     let mut state = state.borrow_mut();
     state.resource_table.add(QueueMessageResource { handle })
@@ -382,18 +441,18 @@ fn op_kv_watch<DBH>(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[serde] keys: Vec<KvKey>,
-) -> Result<ResourceId, AnyError>
+) -> Result<ResourceId, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
-  let resource = state.resource_table.get::<DatabaseResource<DBH::DB>>(rid)?;
+  let resource = state
+    .resource_table
+    .get::<DatabaseResource<DBH::DB>>(rid)
+    .map_err(KvError::Resource)?;
   let config = state.borrow::<Rc<KvConfig>>().clone();
 
   if keys.len() > config.max_watched_keys {
-    return Err(type_error(format!(
-      "Too many keys (max {})",
-      config.max_watched_keys
-    )));
+    return Err(KvError::TooManyKeys(config.max_watched_keys));
   }
 
   let keys: Vec<Vec<u8>> = keys
@@ -428,10 +487,13 @@ enum WatchEntry {
 async fn op_kv_watch_next(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<Vec<WatchEntry>>, AnyError> {
+) -> Result<Option<Vec<WatchEntry>>, KvError> {
   let resource = {
     let state = state.borrow();
-    let resource = state.resource_table.get::<DatabaseWatcherResource>(rid)?;
+    let resource = state
+      .resource_table
+      .get::<DatabaseWatcherResource>(rid)
+      .map_err(KvError::Resource)?;
     resource.clone()
   };
 
@@ -457,7 +519,7 @@ async fn op_kv_watch_next(
     return Ok(None);
   };
 
-  let entries = res?;
+  let entries = res.map_err(KvError::Kv)?;
   let entries = entries
     .into_iter()
     .map(|entry| {
@@ -468,7 +530,7 @@ async fn op_kv_watch_next(
         WatchKeyOutput::Unchanged => WatchEntry::Unchanged,
       })
     })
-    .collect::<Result<_, anyhow::Error>>()?;
+    .collect::<Result<_, KvError>>()?;
 
   Ok(Some(entries))
 }
@@ -478,7 +540,7 @@ async fn op_kv_finish_dequeued_message<DBH>(
   state: Rc<RefCell<OpState>>,
   #[smi] handle_rid: ResourceId,
   success: bool,
-) -> Result<(), AnyError>
+) -> Result<(), KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
@@ -487,9 +549,9 @@ where
     let handle = state
       .resource_table
       .take::<QueueMessageResource<<<DBH>::DB as Database>::QMH>>(handle_rid)
-      .map_err(|_| type_error("Queue message not found"))?;
+      .map_err(|_| KvError::QueueMessageNotFound)?;
     Rc::try_unwrap(handle)
-      .map_err(|_| type_error("Queue message not found"))?
+      .map_err(|_| KvError::QueueMessageNotFound)?
       .handle
   };
   // if we fail to finish the message, there is not much we can do and the
@@ -500,32 +562,52 @@ where
   Ok(())
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum KvCheckError {
+  #[error("invalid versionstamp")]
+  InvalidVersionstamp,
+  #[error(transparent)]
+  Io(std::io::Error),
+}
+
 type V8KvCheck = (KvKey, Option<ByteString>);
 
-fn check_from_v8(value: V8KvCheck) -> Result<Check, AnyError> {
+fn check_from_v8(value: V8KvCheck) -> Result<Check, KvCheckError> {
   let versionstamp = match value.1 {
     Some(data) => {
       let mut out = [0u8; 10];
       if data.len() != out.len() * 2 {
-        bail!(type_error("invalid versionstamp"));
+        return Err(KvCheckError::InvalidVersionstamp);
       }
       faster_hex::hex_decode(&data, &mut out)
-        .map_err(|_| type_error("invalid versionstamp"))?;
+        .map_err(|_| KvCheckError::InvalidVersionstamp)?;
       Some(out)
     }
     None => None,
   };
   Ok(Check {
-    key: encode_v8_key(value.0)?,
+    key: encode_v8_key(value.0).map_err(KvCheckError::Io)?,
     versionstamp,
   })
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum KvMutationError {
+  #[error(transparent)]
+  BigInt(#[from] num_bigint::TryFromBigIntError<num_bigint::BigInt>),
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  #[error("Invalid mutation '{0}' with value")]
+  InvalidMutationWithValue(String),
+  #[error("Invalid mutation '{0}' without value")]
+  InvalidMutationWithoutValue(String),
+}
+
 type V8KvMutation = (KvKey, String, Option<FromV8Value>, Option<u64>);
 
 fn mutation_from_v8(
   (value, current_timstamp): (V8KvMutation, DateTime<Utc>),
-) -> Result<Mutation, AnyError> {
+) -> Result<Mutation, KvMutationError> {
   let key = encode_v8_key(value.0)?;
   let kind = match (value.1.as_str(), value.2) {
     ("set", Some(value)) => MutationKind::Set(value.try_into()?),
@@ -542,10 +624,10 @@ fn mutation_from_v8(
       MutationKind::SetSuffixVersionstampedKey(value.try_into()?)
     }
     (op, Some(_)) => {
-      return Err(type_error(format!("Invalid mutation '{op}' with value")))
+      return Err(KvMutationError::InvalidMutationWithValue(op.to_string()))
     }
     (op, None) => {
-      return Err(type_error(format!("Invalid mutation '{op}' without value")))
+      return Err(KvMutationError::InvalidMutationWithoutValue(op.to_string()))
     }
   };
   Ok(Mutation {
@@ -562,7 +644,7 @@ type V8Enqueue = (JsBuffer, u64, Vec<KvKey>, Option<Vec<u32>>);
 fn enqueue_from_v8(
   value: V8Enqueue,
   current_timestamp: DateTime<Utc>,
-) -> Result<Enqueue, AnyError> {
+) -> Result<Enqueue, std::io::Error> {
   Ok(Enqueue {
     payload: value.0.to_vec(),
     deadline: current_timestamp
@@ -597,7 +679,7 @@ impl RawSelector {
     prefix: Option<KvKey>,
     start: Option<KvKey>,
     end: Option<KvKey>,
-  ) -> Result<Self, AnyError> {
+  ) -> Result<Self, KvError> {
     let prefix = prefix.map(encode_v8_key).transpose()?;
     let start = start.map(encode_v8_key).transpose()?;
     let end = end.map(encode_v8_key).transpose()?;
@@ -610,9 +692,7 @@ impl RawSelector {
       }),
       (Some(prefix), Some(start), None) => {
         if !start.starts_with(&prefix) || start.len() == prefix.len() {
-          return Err(type_error(
-            "Start key is not in the keyspace defined by prefix",
-          ));
+          return Err(KvError::StartKeyNotInKeyspace);
         }
         Ok(Self::Prefixed {
           prefix,
@@ -622,9 +702,7 @@ impl RawSelector {
       }
       (Some(prefix), None, Some(end)) => {
         if !end.starts_with(&prefix) || end.len() == prefix.len() {
-          return Err(type_error(
-            "End key is not in the keyspace defined by prefix",
-          ));
+          return Err(KvError::EndKeyNotInKeyspace);
         }
         Ok(Self::Prefixed {
           prefix,
@@ -634,7 +712,7 @@ impl RawSelector {
       }
       (None, Some(start), Some(end)) => {
         if start > end {
-          return Err(type_error("Start key is greater than end key"));
+          return Err(KvError::StartKeyGreaterThanEndKey);
         }
         Ok(Self::Range { start, end })
       }
@@ -642,7 +720,7 @@ impl RawSelector {
         let end = start.iter().copied().chain(Some(0)).collect();
         Ok(Self::Range { start, end })
       }
-      _ => Err(type_error("Invalid range")),
+      _ => Err(KvError::InvalidRange),
     }
   }
 
@@ -701,10 +779,10 @@ fn common_prefix_for_bytes<'a>(a: &'a [u8], b: &'a [u8]) -> &'a [u8] {
 fn encode_cursor(
   selector: &RawSelector,
   boundary_key: &[u8],
-) -> Result<String, AnyError> {
+) -> Result<String, KvError> {
   let common_prefix = selector.common_prefix();
   if !boundary_key.starts_with(common_prefix) {
-    return Err(type_error("Invalid boundary key"));
+    return Err(KvError::InvalidBoundaryKey);
   }
   Ok(BASE64_URL_SAFE.encode(&boundary_key[common_prefix.len()..]))
 }
@@ -713,7 +791,7 @@ fn decode_selector_and_cursor(
   selector: &RawSelector,
   reverse: bool,
   cursor: Option<&ByteString>,
-) -> Result<(Vec<u8>, Vec<u8>), AnyError> {
+) -> Result<(Vec<u8>, Vec<u8>), KvError> {
   let Some(cursor) = cursor else {
     return Ok((selector.range_start_key(), selector.range_end_key()));
   };
@@ -721,7 +799,7 @@ fn decode_selector_and_cursor(
   let common_prefix = selector.common_prefix();
   let cursor = BASE64_URL_SAFE
     .decode(cursor)
-    .map_err(|_| type_error("invalid cursor"))?;
+    .map_err(|_| KvError::InvalidCursor)?;
 
   let first_key: Vec<u8>;
   let last_key: Vec<u8>;
@@ -746,13 +824,13 @@ fn decode_selector_and_cursor(
   // Defend against out-of-bounds reading
   if let Some(start) = selector.start() {
     if &first_key[..] < start {
-      return Err(type_error("cursor out of bounds"));
+      return Err(KvError::CursorOutOfBounds);
     }
   }
 
   if let Some(end) = selector.end() {
     if &last_key[..] > end {
-      return Err(type_error("cursor out of bounds"));
+      return Err(KvError::CursorOutOfBounds);
     }
   }
 
@@ -767,15 +845,17 @@ async fn op_kv_atomic_write<DBH>(
   #[serde] checks: Vec<V8KvCheck>,
   #[serde] mutations: Vec<V8KvMutation>,
   #[serde] enqueues: Vec<V8Enqueue>,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, KvError>
 where
   DBH: DatabaseHandler + 'static,
 {
   let current_timestamp = chrono::Utc::now();
   let db = {
     let state = state.borrow();
-    let resource =
-      state.resource_table.get::<DatabaseResource<DBH::DB>>(rid)?;
+    let resource = state
+      .resource_table
+      .get::<DatabaseResource<DBH::DB>>(rid)
+      .map_err(KvError::Resource)?;
     resource.db.clone()
   };
 
@@ -785,34 +865,28 @@ where
   };
 
   if checks.len() > config.max_checks {
-    return Err(type_error(format!(
-      "Too many checks (max {})",
-      config.max_checks
-    )));
+    return Err(KvError::TooManyChecks(config.max_checks));
   }
 
   if mutations.len() + enqueues.len() > config.max_mutations {
-    return Err(type_error(format!(
-      "Too many mutations (max {})",
-      config.max_mutations
-    )));
+    return Err(KvError::TooManyMutations(config.max_mutations));
   }
 
   let checks = checks
     .into_iter()
     .map(check_from_v8)
-    .collect::<Result<Vec<Check>, AnyError>>()
-    .with_context(|| "invalid check")?;
+    .collect::<Result<Vec<Check>, KvCheckError>>()
+    .map_err(KvError::InvalidCheck)?;
   let mutations = mutations
     .into_iter()
     .map(|mutation| mutation_from_v8((mutation, current_timestamp)))
-    .collect::<Result<Vec<Mutation>, AnyError>>()
-    .with_context(|| "Invalid mutation")?;
+    .collect::<Result<Vec<Mutation>, KvMutationError>>()
+    .map_err(KvError::InvalidMutation)?;
   let enqueues = enqueues
     .into_iter()
     .map(|e| enqueue_from_v8(e, current_timestamp))
-    .collect::<Result<Vec<Enqueue>, AnyError>>()
-    .with_context(|| "invalid enqueue")?;
+    .collect::<Result<Vec<Enqueue>, std::io::Error>>()
+    .map_err(KvError::InvalidEnqueue)?;
 
   let mut total_payload_size = 0usize;
   let mut total_key_size = 0usize;
@@ -823,7 +897,7 @@ where
     .chain(mutations.iter().map(|m| &m.key))
   {
     if key.is_empty() {
-      return Err(type_error("key cannot be empty"));
+      return Err(KvError::EmptyKey);
     }
 
     total_payload_size += check_write_key_size(key, &config)?;
@@ -847,17 +921,13 @@ where
   }
 
   if total_payload_size > config.max_total_mutation_size_bytes {
-    return Err(type_error(format!(
-      "Total mutation size too large (max {} bytes)",
-      config.max_total_mutation_size_bytes
-    )));
+    return Err(KvError::TotalMutationTooLarge(
+      config.max_total_mutation_size_bytes,
+    ));
   }
 
   if total_key_size > config.max_total_key_size_bytes {
-    return Err(type_error(format!(
-      "Total key size too large (max {} bytes)",
-      config.max_total_key_size_bytes
-    )));
+    return Err(KvError::TotalKeyTooLarge(config.max_total_key_size_bytes));
   }
 
   let atomic_write = AtomicWrite {
@@ -866,7 +936,7 @@ where
     enqueues,
   };
 
-  let result = db.atomic_write(atomic_write).await?;
+  let result = db.atomic_write(atomic_write).await.map_err(KvError::Kv)?;
 
   Ok(result.map(|res| faster_hex::hex_string(&res.versionstamp)))
 }
@@ -879,19 +949,16 @@ type EncodeCursorRangeSelector = (Option<KvKey>, Option<KvKey>, Option<KvKey>);
 fn op_kv_encode_cursor(
   #[serde] (prefix, start, end): EncodeCursorRangeSelector,
   #[serde] boundary_key: KvKey,
-) -> Result<String, AnyError> {
+) -> Result<String, KvError> {
   let selector = RawSelector::from_tuple(prefix, start, end)?;
   let boundary_key = encode_v8_key(boundary_key)?;
   let cursor = encode_cursor(&selector, &boundary_key)?;
   Ok(cursor)
 }
 
-fn check_read_key_size(key: &[u8], config: &KvConfig) -> Result<(), AnyError> {
+fn check_read_key_size(key: &[u8], config: &KvConfig) -> Result<(), KvError> {
   if key.len() > config.max_read_key_size_bytes {
-    Err(type_error(format!(
-      "Key too large for read (max {} bytes)",
-      config.max_read_key_size_bytes
-    )))
+    Err(KvError::KeyTooLargeToRead(config.max_read_key_size_bytes))
   } else {
     Ok(())
   }
@@ -900,12 +967,9 @@ fn check_read_key_size(key: &[u8], config: &KvConfig) -> Result<(), AnyError> {
 fn check_write_key_size(
   key: &[u8],
   config: &KvConfig,
-) -> Result<usize, AnyError> {
+) -> Result<usize, KvError> {
   if key.len() > config.max_write_key_size_bytes {
-    Err(type_error(format!(
-      "Key too large for write (max {} bytes)",
-      config.max_write_key_size_bytes
-    )))
+    Err(KvError::KeyTooLargeToWrite(config.max_write_key_size_bytes))
   } else {
     Ok(key.len())
   }
@@ -914,7 +978,7 @@ fn check_write_key_size(
 fn check_value_size(
   value: &KvValue,
   config: &KvConfig,
-) -> Result<usize, AnyError> {
+) -> Result<usize, KvError> {
   let payload = match value {
     KvValue::Bytes(x) => x,
     KvValue::V8(x) => x,
@@ -922,10 +986,7 @@ fn check_value_size(
   };
 
   if payload.len() > config.max_value_size_bytes {
-    Err(type_error(format!(
-      "Value too large (max {} bytes)",
-      config.max_value_size_bytes
-    )))
+    Err(KvError::ValueTooLarge(config.max_value_size_bytes))
   } else {
     Ok(payload.len())
   }
@@ -934,12 +995,9 @@ fn check_value_size(
 fn check_enqueue_payload_size(
   payload: &[u8],
   config: &KvConfig,
-) -> Result<usize, AnyError> {
+) -> Result<usize, KvError> {
   if payload.len() > config.max_value_size_bytes {
-    Err(type_error(format!(
-      "enqueue payload too large (max {} bytes)",
-      config.max_value_size_bytes
-    )))
+    Err(KvError::EnqueuePayloadTooLarge(config.max_value_size_bytes))
   } else {
     Ok(payload.len())
   }
diff --git a/ext/napi/Cargo.toml b/ext/napi/Cargo.toml
index ade789ff80..c31367118e 100644
--- a/ext/napi/Cargo.toml
+++ b/ext/napi/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_napi"
-version = "0.102.0"
+version = "0.106.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -16,4 +16,14 @@ path = "lib.rs"
 [dependencies]
 deno_core.workspace = true
 deno_permissions.workspace = true
+libc.workspace = true
 libloading = { version = "0.7" }
+log.workspace = true
+napi_sym.workspace = true
+thiserror.workspace = true
+
+[target.'cfg(windows)'.dependencies]
+windows-sys.workspace = true
+
+[dev-dependencies]
+libuv-sys-lite = "=1.48.2"
diff --git a/ext/napi/README.md b/ext/napi/README.md
index e69de29bb2..b479295244 100644
--- a/ext/napi/README.md
+++ b/ext/napi/README.md
@@ -0,0 +1,114 @@
+# napi
+
+This directory contains source for Deno's Node-API implementation. It depends on
+`napi_sym` and `deno_napi`.
+
+Files are generally organized the same as in Node.js's implementation to ease in
+ensuring compatibility.
+
+## Adding a new function
+
+Add the symbol name to
+[`cli/napi_sym/symbol_exports.json`](../napi_sym/symbol_exports.json).
+
+```diff
+{
+  "symbols": [
+    ...
+    "napi_get_undefined",
+-   "napi_get_null"
++   "napi_get_null",
++   "napi_get_boolean"
+  ]
+}
+```
+
+Determine where to place the implementation. `napi_get_boolean` is related to JS
+values so we will place it in `js_native_api.rs`. If something is not clear,
+just create a new file module.
+
+See [`napi_sym`](../napi_sym/) for writing the implementation:
+
+```rust
+#[napi_sym::napi_sym]
+fn napi_get_boolean(
+  env: *mut Env,
+  value: bool,
+  result: *mut napi_value,
+) -> Result {
+  // ...
+  Ok(())
+}
+```
+
+Update the generated symbol lists using the script:
+
+```
+deno run --allow-write tools/napi/generate_symbols_lists.js
+```
+
+Add a test in [`/tests/napi`](../../tests/napi/). You can also refer to Node.js
+test suite for Node-API.
+
+```js
+// tests/napi/boolean_test.js
+import { assertEquals, loadTestLibrary } from "./common.js";
+const lib = loadTestLibrary();
+Deno.test("napi get boolean", function () {
+  assertEquals(lib.test_get_boolean(true), true);
+  assertEquals(lib.test_get_boolean(false), false);
+});
+```
+
+```rust
+// tests/napi/src/boolean.rs
+
+use napi_sys::Status::napi_ok;
+use napi_sys::ValueType::napi_boolean;
+use napi_sys::*;
+
+extern "C" fn test_boolean(
+  env: napi_env,
+  info: napi_callback_info,
+) -> napi_value {
+  let (args, argc, _) = crate::get_callback_info!(env, info, 1);
+  assert_eq!(argc, 1);
+
+  let mut ty = -1;
+  assert!(unsafe { napi_typeof(env, args[0], &mut ty) } == napi_ok);
+  assert_eq!(ty, napi_boolean);
+
+  // Use napi_get_boolean here...
+
+  value
+}
+
+pub fn init(env: napi_env, exports: napi_value) {
+  let properties = &[crate::new_property!(env, "test_boolean\0", test_boolean)];
+
+  unsafe {
+    napi_define_properties(env, exports, properties.len(), properties.as_ptr())
+  };
+}
+```
+
+```diff
+// tests/napi/src/lib.rs
+
++ mod boolean;
+
+...
+
+#[no_mangle]
+unsafe extern "C" fn napi_register_module_v1(
+  env: napi_env,
+  exports: napi_value,
+) -> napi_value {
+  ...
++ boolean::init(env, exports);
+
+  exports
+}
+```
+
+Run the test using `cargo test -p tests/napi`.
diff --git a/ext/napi/build.rs b/ext/napi/build.rs
new file mode 100644
index 0000000000..8705830a95
--- /dev/null
+++ b/ext/napi/build.rs
@@ -0,0 +1,22 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+
+fn main() {
+  let symbols_file_name = match std::env::consts::OS {
+    "android" | "freebsd" | "openbsd" => {
+      "generated_symbol_exports_list_linux.def".to_string()
+    }
+    os => format!("generated_symbol_exports_list_{}.def", os),
+  };
+  let symbols_path = std::path::Path::new(".")
+    .join(symbols_file_name)
+    .canonicalize()
+    .expect(
+        "Missing symbols list! Generate using tools/napi/generate_symbols_lists.js",
+    );
+
+  println!("cargo:rustc-rerun-if-changed={}", symbols_path.display());
+
+  let path = std::path::PathBuf::from(std::env::var("OUT_DIR").unwrap())
+    .join("napi_symbol_path.txt");
+  std::fs::write(path, symbols_path.as_os_str().as_encoded_bytes()).unwrap();
+}
diff --git a/cli/napi/generated_symbol_exports_list_linux.def b/ext/napi/generated_symbol_exports_list_linux.def
similarity index 100%
rename from cli/napi/generated_symbol_exports_list_linux.def
rename to ext/napi/generated_symbol_exports_list_linux.def
diff --git a/cli/napi/generated_symbol_exports_list_macos.def b/ext/napi/generated_symbol_exports_list_macos.def
similarity index 100%
rename from cli/napi/generated_symbol_exports_list_macos.def
rename to ext/napi/generated_symbol_exports_list_macos.def
diff --git a/cli/napi/generated_symbol_exports_list_windows.def b/ext/napi/generated_symbol_exports_list_windows.def
similarity index 100%
rename from cli/napi/generated_symbol_exports_list_windows.def
rename to ext/napi/generated_symbol_exports_list_windows.def
diff --git a/cli/napi/js_native_api.rs b/ext/napi/js_native_api.rs
similarity index 98%
rename from cli/napi/js_native_api.rs
rename to ext/napi/js_native_api.rs
index e922d8c3f2..53a12d6eba 100644
--- a/cli/napi/js_native_api.rs
+++ b/ext/napi/js_native_api.rs
@@ -5,7 +5,7 @@
 
 const NAPI_VERSION: u32 = 9;
 
-use deno_runtime::deno_napi::*;
+use crate::*;
 use libc::INT_MAX;
 
 use super::util::check_new_from_utf8;
@@ -17,9 +17,9 @@ use super::util::napi_set_last_error;
 use super::util::v8_name_from_property_descriptor;
 use crate::check_arg;
 use crate::check_env;
-use deno_runtime::deno_napi::function::create_function;
-use deno_runtime::deno_napi::function::create_function_template;
-use deno_runtime::deno_napi::function::CallbackInfo;
+use crate::function::create_function;
+use crate::function::create_function_template;
+use crate::function::CallbackInfo;
 use napi_sym::napi_sym;
 use std::ptr::NonNull;
 
@@ -264,6 +264,16 @@ fn napi_define_class<'s>(
       Err(status) => return status,
     };
 
+    let mut accessor_property = v8::PropertyAttribute::NONE;
+
+    if p.attributes & napi_enumerable == 0 {
+      accessor_property = accessor_property | v8::PropertyAttribute::DONT_ENUM;
+    }
+    if p.attributes & napi_configurable == 0 {
+      accessor_property =
+        accessor_property | v8::PropertyAttribute::DONT_DELETE;
+    }
+
     if p.getter.is_some() || p.setter.is_some() {
       let getter = p.getter.map(|g| {
         create_function_template(&mut env.scope(), env_ptr, None, g, p.data)
@@ -271,8 +281,6 @@ fn napi_define_class<'s>(
       let setter = p.setter.map(|s| {
         create_function_template(&mut env.scope(), env_ptr, None, s, p.data)
       });
-
-      let mut accessor_property = v8::PropertyAttribute::NONE;
       if getter.is_some()
         && setter.is_some()
         && (p.attributes & napi_writable) == 0
@@ -280,15 +288,6 @@ fn napi_define_class<'s>(
         accessor_property =
           accessor_property | v8::PropertyAttribute::READ_ONLY;
       }
-      if p.attributes & napi_enumerable == 0 {
-        accessor_property =
-          accessor_property | v8::PropertyAttribute::DONT_ENUM;
-      }
-      if p.attributes & napi_configurable == 0 {
-        accessor_property =
-          accessor_property | v8::PropertyAttribute::DONT_DELETE;
-      }
-
       let proto = tpl.prototype_template(&mut env.scope());
       proto.set_accessor_property(name, getter, setter, accessor_property);
     } else if let Some(method) = p.method {
@@ -300,10 +299,14 @@ fn napi_define_class<'s>(
         p.data,
       );
       let proto = tpl.prototype_template(&mut env.scope());
-      proto.set(name, function.into());
+      proto.set_with_attr(name, function.into(), accessor_property);
     } else {
       let proto = tpl.prototype_template(&mut env.scope());
-      proto.set(name, p.value.unwrap().into());
+      if (p.attributes & napi_writable) == 0 {
+        accessor_property =
+          accessor_property | v8::PropertyAttribute::READ_ONLY;
+      }
+      proto.set_with_attr(name, p.value.unwrap().into(), accessor_property);
     }
   }
 
@@ -1080,7 +1083,7 @@ fn napi_create_string_latin1(
 }
 
 #[napi_sym]
-fn napi_create_string_utf8(
+pub(crate) fn napi_create_string_utf8(
   env_ptr: *mut Env,
   string: *const c_char,
   length: usize,
@@ -1644,7 +1647,7 @@ fn napi_get_cb_info(
     check_arg!(env, argc);
     let argc = unsafe { *argc as usize };
     for i in 0..argc {
-      let mut arg = args.get(i as _);
+      let arg = args.get(i as _);
       unsafe {
         *argv.add(i) = arg.into();
       }
@@ -1694,15 +1697,14 @@ fn napi_get_new_target(
 }
 
 #[napi_sym]
-fn napi_call_function(
-  env_ptr: *mut Env,
-  recv: napi_value,
-  func: napi_value,
+fn napi_call_function<'s>(
+  env: &'s mut Env,
+  recv: napi_value<'s>,
+  func: napi_value<'s>,
   argc: usize,
-  argv: *const napi_value,
-  result: *mut napi_value,
+  argv: *const napi_value<'s>,
+  result: *mut napi_value<'s>,
 ) -> napi_status {
-  let env = check_env!(env_ptr);
   check_arg!(env, recv);
   let args = if argc > 0 {
     check_arg!(env, argv);
@@ -1716,11 +1718,11 @@ fn napi_call_function(
   let Some(func) =
     func.and_then(|f| v8::Local::<v8::Function>::try_from(f).ok())
   else {
-    return napi_set_last_error(env, napi_function_expected);
+    return napi_function_expected;
   };
 
   let Some(v) = func.call(&mut env.scope(), recv.unwrap(), args) else {
-    return napi_set_last_error(env_ptr, napi_generic_failure);
+    return napi_generic_failure;
   };
 
   if !result.is_null() {
@@ -1729,7 +1731,7 @@ fn napi_call_function(
     }
   }
 
-  return napi_clear_last_error(env_ptr);
+  napi_ok
 }
 
 #[napi_sym]
diff --git a/ext/napi/lib.rs b/ext/napi/lib.rs
index 4500c66fd4..20f924bdbf 100644
--- a/ext/napi/lib.rs
+++ b/ext/napi/lib.rs
@@ -5,9 +5,23 @@
 #![allow(clippy::undocumented_unsafe_blocks)]
 #![deny(clippy::missing_safety_doc)]
 
+//! Symbols to be exported are now defined in this JSON file.
+//! The `#[napi_sym]` macro checks for missing entries and panics.
+//!
+//! `./tools/napi/generate_symbols_list.js` is used to generate the LINK `cli/exports.def` on Windows,
+//! which is also checked into git.
+//!
+//! To add a new napi function:
+//! 1. Place `#[napi_sym]` on top of your implementation.
+//! 2. Add the function's identifier to this JSON list.
+//! 3. Finally, run `tools/napi/generate_symbols_list.js` to update `ext/napi/generated_symbol_exports_list_*.def`.
+
+pub mod js_native_api;
+pub mod node_api;
+pub mod util;
+pub mod uv;
+
 use core::ptr::NonNull;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::parking_lot::RwLock;
 use deno_core::url::Url;
@@ -20,6 +34,18 @@ use std::path::PathBuf;
 use std::rc::Rc;
 use std::thread_local;
 
+#[derive(Debug, thiserror::Error)]
+pub enum NApiError {
+  #[error("Invalid path")]
+  InvalidPath,
+  #[error(transparent)]
+  LibLoading(#[from] libloading::Error),
+  #[error("Unable to find register Node-API module at {}", .0.display())]
+  ModuleNotFound(PathBuf),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+}
+
 #[cfg(unix)]
 use libloading::os::unix::*;
 
@@ -482,14 +508,20 @@ deno_core::extension!(deno_napi,
 
 pub trait NapiPermissions {
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
-  fn check(&mut self, path: &str) -> std::result::Result<PathBuf, AnyError>;
+  fn check(
+    &mut self,
+    path: &str,
+  ) -> Result<PathBuf, deno_core::error::AnyError>;
 }
 
 // NOTE(bartlomieju): for now, NAPI uses `--allow-ffi` flag, but that might
 // change in the future.
 impl NapiPermissions for deno_permissions::PermissionsContainer {
   #[inline(always)]
-  fn check(&mut self, path: &str) -> Result<PathBuf, AnyError> {
+  fn check(
+    &mut self,
+    path: &str,
+  ) -> Result<PathBuf, deno_core::error::AnyError> {
     deno_permissions::PermissionsContainer::check_ffi(self, path)
   }
 }
@@ -512,7 +544,7 @@ fn op_napi_open<NP, 'scope>(
   global: v8::Local<'scope, v8::Object>,
   buffer_constructor: v8::Local<'scope, v8::Function>,
   report_error: v8::Local<'scope, v8::Function>,
-) -> std::result::Result<v8::Local<'scope, v8::Value>, AnyError>
+) -> Result<v8::Local<'scope, v8::Value>, NApiError>
 where
   NP: NapiPermissions + 'static,
 {
@@ -521,7 +553,7 @@ where
   let (async_work_sender, cleanup_hooks, external_ops_tracker, path) = {
     let mut op_state = op_state.borrow_mut();
     let permissions = op_state.borrow_mut::<NP>();
-    let path = permissions.check(&path)?;
+    let path = permissions.check(&path).map_err(NApiError::Permission)?;
     let napi_state = op_state.borrow::<NapiState>();
     (
       op_state.borrow::<V8CrossThreadTaskSpawner>().clone(),
@@ -540,7 +572,7 @@ where
   let type_tag = v8::Global::new(scope, type_tag);
 
   let url_filename =
-    Url::from_file_path(&path).map_err(|_| type_error("Invalid path"))?;
+    Url::from_file_path(&path).map_err(|_| NApiError::InvalidPath)?;
   let env_shared =
     EnvShared::new(napi_wrap, type_tag, format!("{url_filename}\0"));
 
@@ -565,17 +597,11 @@ where
 
   // SAFETY: opening a DLL calls dlopen
   #[cfg(unix)]
-  let library = match unsafe { Library::open(Some(&path), flags) } {
-    Ok(lib) => lib,
-    Err(e) => return Err(type_error(e.to_string())),
-  };
+  let library = unsafe { Library::open(Some(&path), flags) }?;
 
   // SAFETY: opening a DLL calls dlopen
   #[cfg(not(unix))]
-  let library = match unsafe { Library::load_with_flags(&path, flags) } {
-    Ok(lib) => lib,
-    Err(e) => return Err(type_error(e.to_string())),
-  };
+  let library = unsafe { Library::load_with_flags(&path, flags) }?;
 
   let maybe_module = MODULE_TO_REGISTER.with(|cell| {
     let mut slot = cell.borrow_mut();
@@ -610,10 +636,7 @@ where
     // SAFETY: we are going blind, calling the register function on the other side.
     unsafe { init(env_ptr, exports.into()) }
   } else {
-    return Err(type_error(format!(
-      "Unable to find register Node-API module at {}",
-      path.display()
-    )));
+    return Err(NApiError::ModuleNotFound(path));
   };
 
   let exports = maybe_exports.unwrap_or(exports.into());
@@ -624,3 +647,34 @@ where
 
   Ok(exports)
 }
+
+#[allow(clippy::print_stdout)]
+pub fn print_linker_flags(name: &str) {
+  let symbols_path =
+    include_str!(concat!(env!("OUT_DIR"), "/napi_symbol_path.txt"));
+
+  #[cfg(target_os = "windows")]
+  println!("cargo:rustc-link-arg-bin={name}=/DEF:{}", symbols_path);
+
+  #[cfg(target_os = "macos")]
+  println!(
+    "cargo:rustc-link-arg-bin={name}=-Wl,-exported_symbols_list,{}",
+    symbols_path,
+  );
+
+  #[cfg(any(
+    target_os = "linux",
+    target_os = "freebsd",
+    target_os = "openbsd"
+  ))]
+  println!(
+    "cargo:rustc-link-arg-bin={name}=-Wl,--export-dynamic-symbol-list={}",
+    symbols_path,
+  );
+
+  #[cfg(target_os = "android")]
+  println!(
+    "cargo:rustc-link-arg-bin={name}=-Wl,--export-dynamic-symbol-list={}",
+    symbols_path,
+  );
+}
diff --git a/cli/napi/node_api.rs b/ext/napi/node_api.rs
similarity index 98%
rename from cli/napi/node_api.rs
rename to ext/napi/node_api.rs
index 2efb71c267..186ae42c48 100644
--- a/cli/napi/node_api.rs
+++ b/ext/napi/node_api.rs
@@ -9,10 +9,10 @@ use super::util::napi_set_last_error;
 use super::util::SendPtr;
 use crate::check_arg;
 use crate::check_env;
+use crate::*;
 use deno_core::parking_lot::Condvar;
 use deno_core::parking_lot::Mutex;
 use deno_core::V8CrossThreadTaskSpawner;
-use deno_runtime::deno_napi::*;
 use napi_sym::napi_sym;
 use std::sync::atomic::AtomicBool;
 use std::sync::atomic::AtomicU8;
@@ -488,7 +488,7 @@ impl AsyncWork {
 }
 
 #[napi_sym]
-fn napi_create_async_work(
+pub(crate) fn napi_create_async_work(
   env: *mut Env,
   async_resource: napi_value,
   async_resource_name: napi_value,
@@ -537,7 +537,10 @@ fn napi_create_async_work(
 }
 
 #[napi_sym]
-fn napi_delete_async_work(env: *mut Env, work: napi_async_work) -> napi_status {
+pub(crate) fn napi_delete_async_work(
+  env: *mut Env,
+  work: napi_async_work,
+) -> napi_status {
   let env = check_env!(env);
   check_arg!(env, work);
 
@@ -560,7 +563,10 @@ fn napi_get_uv_event_loop(
 }
 
 #[napi_sym]
-fn napi_queue_async_work(env: *mut Env, work: napi_async_work) -> napi_status {
+pub(crate) fn napi_queue_async_work(
+  env: *mut Env,
+  work: napi_async_work,
+) -> napi_status {
   let env = check_env!(env);
   check_arg!(env, work);
 
@@ -692,7 +698,7 @@ impl Drop for TsFn {
 
     if let Some(finalizer) = self.thread_finalize_cb {
       unsafe {
-        (finalizer)(self.env as _, self.thread_finalize_data, ptr::null_mut());
+        (finalizer)(self.env as _, self.thread_finalize_data, self.context);
       }
     }
   }
@@ -897,7 +903,7 @@ fn napi_create_threadsafe_function(
   };
   let resource_name = resource_name.to_rust_string_lossy(&mut env.scope());
 
-  let mut tsfn = Box::new(TsFn {
+  let tsfn = Box::new(TsFn {
     env,
     func,
     max_queue_size,
diff --git a/cli/napi/sym/Cargo.toml b/ext/napi/sym/Cargo.toml
similarity index 95%
rename from cli/napi/sym/Cargo.toml
rename to ext/napi/sym/Cargo.toml
index fef749fc46..c23054eb40 100644
--- a/cli/napi/sym/Cargo.toml
+++ b/ext/napi/sym/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "napi_sym"
-version = "0.101.0"
+version = "0.105.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/cli/napi/sym/README.md b/ext/napi/sym/README.md
similarity index 92%
rename from cli/napi/sym/README.md
rename to ext/napi/sym/README.md
index de08a8e174..66eb4bff26 100644
--- a/cli/napi/sym/README.md
+++ b/ext/napi/sym/README.md
@@ -2,7 +2,8 @@
 
 A proc_macro for Deno's Node-API implementation. It does the following things:
 
-- Marks the symbol as `#[no_mangle]` and rewrites it as `pub extern "C" $name`.
+- Marks the symbol as `#[no_mangle]` and rewrites it as
+  `unsafe extern "C" $name`.
 - Asserts that the function symbol is present in
   [`symbol_exports.json`](./symbol_exports.json).
 - Maps `deno_napi::Result` to raw `napi_result`.
diff --git a/cli/napi/sym/lib.rs b/ext/napi/sym/lib.rs
similarity index 100%
rename from cli/napi/sym/lib.rs
rename to ext/napi/sym/lib.rs
diff --git a/cli/napi/sym/symbol_exports.json b/ext/napi/sym/symbol_exports.json
similarity index 100%
rename from cli/napi/sym/symbol_exports.json
rename to ext/napi/sym/symbol_exports.json
diff --git a/cli/napi/util.rs b/ext/napi/util.rs
similarity index 84%
rename from cli/napi/util.rs
rename to ext/napi/util.rs
index 63d8effbf2..21e9d433aa 100644
--- a/cli/napi/util.rs
+++ b/ext/napi/util.rs
@@ -1,9 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_runtime::deno_napi::*;
+use crate::*;
 use libc::INT_MAX;
 
 #[repr(transparent)]
-pub struct SendPtr<T>(pub *const T);
+pub(crate) struct SendPtr<T>(pub *const T);
 
 impl<T> SendPtr<T> {
   // silly function to get around `clippy::redundant_locals`
@@ -37,7 +37,7 @@ impl Drop for BufferFinalizer {
   }
 }
 
-pub extern "C" fn backing_store_deleter_callback(
+pub(crate) extern "C" fn backing_store_deleter_callback(
   data: *mut c_void,
   _byte_length: usize,
   deleter_data: *mut c_void,
@@ -50,7 +50,7 @@ pub extern "C" fn backing_store_deleter_callback(
   drop(finalizer);
 }
 
-pub fn make_external_backing_store(
+pub(crate) fn make_external_backing_store(
   env: *mut Env,
   data: *mut c_void,
   byte_length: usize,
@@ -90,9 +90,7 @@ macro_rules! check_env {
 macro_rules! return_error_status_if_false {
   ($env: expr, $condition: expr, $status: ident) => {
     if !$condition {
-      return Err(
-        $crate::napi::util::napi_set_last_error($env, $status).into(),
-      );
+      return Err($crate::util::napi_set_last_error($env, $status).into());
     }
   };
 }
@@ -101,7 +99,7 @@ macro_rules! return_error_status_if_false {
 macro_rules! return_status_if_false {
   ($env: expr, $condition: expr, $status: ident) => {
     if !$condition {
-      return $crate::napi::util::napi_set_last_error($env, $status);
+      return $crate::util::napi_set_last_error($env, $status);
     }
   };
 }
@@ -222,7 +220,7 @@ macro_rules! check_arg {
   ($env: expr, $ptr: expr) => {
     $crate::return_status_if_false!(
       $env,
-      !$crate::napi::util::Nullable::is_null(&$ptr),
+      !$crate::util::Nullable::is_null(&$ptr),
       napi_invalid_arg
     );
   };
@@ -230,17 +228,17 @@ macro_rules! check_arg {
 
 #[macro_export]
 macro_rules! napi_wrap {
-  ( $( # $attr:tt )* fn $name:ident $( < $( $x:lifetime ),* > )? ( $env:ident : & $( $lt:lifetime )? mut Env $( , $ident:ident : $ty:ty )* $(,)? ) -> napi_status $body:block ) => {
-    $( # $attr )*
+  ( $( # [ $attr:meta ] )* $vis:vis fn $name:ident $( < $( $x:lifetime ),* > )? ( $env:ident : & $( $lt:lifetime )? mut Env $( , $ident:ident : $ty:ty )* $(,)? ) -> napi_status $body:block ) => {
+    $( # [ $attr ] )*
     #[no_mangle]
-    pub unsafe extern "C" fn $name $( < $( $x ),* > )? ( env_ptr : *mut Env , $( $ident : $ty ),* ) -> napi_status {
+    $vis unsafe extern "C" fn $name $( < $( $x ),* > )? ( env_ptr : *mut Env , $( $ident : $ty ),* ) -> napi_status {
       let env: & $( $lt )? mut Env = $crate::check_env!(env_ptr);
 
       if env.last_exception.is_some() {
         return napi_pending_exception;
       }
 
-      $crate::napi::util::napi_clear_last_error(env);
+      $crate::util::napi_clear_last_error(env);
 
       let scope_env = unsafe { &mut *env_ptr };
       let scope = &mut scope_env.scope();
@@ -259,21 +257,21 @@ macro_rules! napi_wrap {
         let env = unsafe { &mut *env_ptr };
         let global = v8::Global::new(env.isolate(), exception);
         env.last_exception = Some(global);
-        return $crate::napi::util::napi_set_last_error(env_ptr, napi_pending_exception);
+        return $crate::util::napi_set_last_error(env_ptr, napi_pending_exception);
       }
 
       if result != napi_ok {
-        return $crate::napi::util::napi_set_last_error(env_ptr, result);
+        return $crate::util::napi_set_last_error(env_ptr, result);
       }
 
       return result;
     }
   };
 
-  ( $( # $attr:tt )* fn $name:ident $( < $( $x:lifetime ),* > )? ( $( $ident:ident : $ty:ty ),* $(,)? ) -> napi_status $body:block ) => {
-    $( # $attr )*
+  ( $( # [ $attr:meta ] )* $vis:vis fn $name:ident $( < $( $x:lifetime ),* > )? ( $( $ident:ident : $ty:ty ),* $(,)? ) -> napi_status $body:block ) => {
+    $( # [ $attr ] )*
     #[no_mangle]
-    pub unsafe extern "C" fn $name $( < $( $x ),* > )? ( $( $ident : $ty ),* ) -> napi_status {
+    $vis unsafe extern "C" fn $name $( < $( $x ),* > )? ( $( $ident : $ty ),* ) -> napi_status {
       #[inline(always)]
       fn inner $( < $( $x ),* > )? ( $( $ident : $ty ),* ) -> napi_status $body
 
diff --git a/cli/napi/uv.rs b/ext/napi/uv.rs
similarity index 95%
rename from cli/napi/uv.rs
rename to ext/napi/uv.rs
index d4cb5c0b36..6f728a92b3 100644
--- a/cli/napi/uv.rs
+++ b/ext/napi/uv.rs
@@ -1,7 +1,7 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use crate::*;
 use deno_core::parking_lot::Mutex;
-use deno_runtime::deno_napi::*;
 use std::mem::MaybeUninit;
 use std::ptr::addr_of_mut;
 
@@ -16,10 +16,10 @@ fn assert_ok(res: c_int) -> c_int {
   res
 }
 
-use crate::napi::js_native_api::napi_create_string_utf8;
-use crate::napi::node_api::napi_create_async_work;
-use crate::napi::node_api::napi_delete_async_work;
-use crate::napi::node_api::napi_queue_async_work;
+use js_native_api::napi_create_string_utf8;
+use node_api::napi_create_async_work;
+use node_api::napi_delete_async_work;
+use node_api::napi_queue_async_work;
 use std::ffi::c_int;
 
 const UV_MUTEX_SIZE: usize = {
diff --git a/ext/net/01_net.js b/ext/net/01_net.js
index 5b894947ee..c3e5f9e5ca 100644
--- a/ext/net/01_net.js
+++ b/ext/net/01_net.js
@@ -194,6 +194,20 @@ class Conn {
   }
 }
 
+class UpgradedConn extends Conn {
+  #rid = 0;
+
+  constructor(rid, remoteAddr, localAddr) {
+    super(rid, remoteAddr, localAddr);
+    ObjectDefineProperty(this, internalRidSymbol, {
+      __proto__: null,
+      enumerable: false,
+      value: rid,
+    });
+    this.#rid = rid;
+  }
+}
+
 class TcpConn extends Conn {
   #rid = 0;
 
@@ -601,5 +615,6 @@ export {
   resolveDns,
   TcpConn,
   UnixConn,
+  UpgradedConn,
   validatePort,
 };
diff --git a/ext/net/Cargo.toml b/ext/net/Cargo.toml
index 9f72456b90..5ffd1b4504 100644
--- a/ext/net/Cargo.toml
+++ b/ext/net/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_net"
-version = "0.163.0"
+version = "0.167.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -21,6 +21,7 @@ pin-project.workspace = true
 rustls-tokio-stream.workspace = true
 serde.workspace = true
 socket2.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
 trust-dns-proto = "0.23"
 trust-dns-resolver = { version = "0.23", features = ["tokio-runtime", "serde-config"] }
diff --git a/ext/net/io.rs b/ext/net/io.rs
index f3aed3fcbd..2907fa398b 100644
--- a/ext/net/io.rs
+++ b/ext/net/io.rs
@@ -1,7 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
+use deno_core::futures::TryFutureExt;
 use deno_core::AsyncMutFuture;
 use deno_core::AsyncRefCell;
 use deno_core::AsyncResult;
@@ -69,25 +68,36 @@ where
   pub async fn read(
     self: Rc<Self>,
     data: &mut [u8],
-  ) -> Result<usize, AnyError> {
+  ) -> Result<usize, std::io::Error> {
     let mut rd = self.rd_borrow_mut().await;
     let nread = rd.read(data).try_or_cancel(self.cancel_handle()).await?;
     Ok(nread)
   }
 
-  pub async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, AnyError> {
+  pub async fn write(
+    self: Rc<Self>,
+    data: &[u8],
+  ) -> Result<usize, std::io::Error> {
     let mut wr = self.wr_borrow_mut().await;
     let nwritten = wr.write(data).await?;
     Ok(nwritten)
   }
 
-  pub async fn shutdown(self: Rc<Self>) -> Result<(), AnyError> {
+  pub async fn shutdown(self: Rc<Self>) -> Result<(), std::io::Error> {
     let mut wr = self.wr_borrow_mut().await;
     wr.shutdown().await?;
     Ok(())
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum MapError {
+  #[error("{0}")]
+  Io(std::io::Error),
+  #[error("Unable to get resources")]
+  NoResources,
+}
+
 pub type TcpStreamResource =
   FullDuplexResource<tcp::OwnedReadHalf, tcp::OwnedWriteHalf>;
 
@@ -100,7 +110,7 @@ impl Resource for TcpStreamResource {
   }
 
   fn shutdown(self: Rc<Self>) -> AsyncResult<()> {
-    Box::pin(self.shutdown())
+    Box::pin(self.shutdown().map_err(Into::into))
   }
 
   fn close(self: Rc<Self>) {
@@ -109,31 +119,30 @@ impl Resource for TcpStreamResource {
 }
 
 impl TcpStreamResource {
-  pub fn set_nodelay(self: Rc<Self>, nodelay: bool) -> Result<(), AnyError> {
-    self.map_socket(Box::new(move |socket| Ok(socket.set_nodelay(nodelay)?)))
+  pub fn set_nodelay(self: Rc<Self>, nodelay: bool) -> Result<(), MapError> {
+    self.map_socket(Box::new(move |socket| socket.set_nodelay(nodelay)))
   }
 
   pub fn set_keepalive(
     self: Rc<Self>,
     keepalive: bool,
-  ) -> Result<(), AnyError> {
-    self
-      .map_socket(Box::new(move |socket| Ok(socket.set_keepalive(keepalive)?)))
+  ) -> Result<(), MapError> {
+    self.map_socket(Box::new(move |socket| socket.set_keepalive(keepalive)))
   }
 
   #[allow(clippy::type_complexity)]
   fn map_socket(
     self: Rc<Self>,
-    map: Box<dyn FnOnce(SockRef) -> Result<(), AnyError>>,
-  ) -> Result<(), AnyError> {
+    map: Box<dyn FnOnce(SockRef) -> Result<(), std::io::Error>>,
+  ) -> Result<(), MapError> {
     if let Some(wr) = RcRef::map(self, |r| &r.wr).try_borrow() {
       let stream = wr.as_ref().as_ref();
       let socket = socket2::SockRef::from(stream);
 
-      return map(socket);
+      return map(socket).map_err(MapError::Io);
     }
 
-    Err(generic_error("Unable to get resources"))
+    Err(MapError::NoResources)
   }
 }
 
@@ -153,7 +162,9 @@ impl UnixStreamResource {
     unreachable!()
   }
   #[allow(clippy::unused_async)]
-  pub async fn shutdown(self: Rc<Self>) -> Result<(), AnyError> {
+  pub async fn shutdown(
+    self: Rc<Self>,
+  ) -> Result<(), deno_core::error::AnyError> {
     unreachable!()
   }
   pub fn cancel_read_ops(&self) {
@@ -170,7 +181,7 @@ impl Resource for UnixStreamResource {
   }
 
   fn shutdown(self: Rc<Self>) -> AsyncResult<()> {
-    Box::pin(self.shutdown())
+    Box::pin(self.shutdown().map_err(Into::into))
   }
 
   fn close(self: Rc<Self>) {
diff --git a/ext/net/ops.rs b/ext/net/ops.rs
index 5248493f41..0f92dead0c 100644
--- a/ext/net/ops.rs
+++ b/ext/net/ops.rs
@@ -6,10 +6,6 @@ use crate::resolve_addr::resolve_addr;
 use crate::resolve_addr::resolve_addr_sync;
 use crate::tcp::TcpListener;
 use crate::NetPermissions;
-use deno_core::error::bad_resource;
-use deno_core::error::custom_error;
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::CancelFuture;
 
@@ -43,6 +39,7 @@ use trust_dns_proto::rr::record_type::RecordType;
 use trust_dns_resolver::config::NameServerConfigGroup;
 use trust_dns_resolver::config::ResolverConfig;
 use trust_dns_resolver::config::ResolverOpts;
+use trust_dns_resolver::error::ResolveError;
 use trust_dns_resolver::error::ResolveErrorKind;
 use trust_dns_resolver::system_conf;
 use trust_dns_resolver::AsyncResolver;
@@ -68,11 +65,69 @@ impl From<SocketAddr> for IpAddr {
   }
 }
 
-pub(crate) fn accept_err(e: std::io::Error) -> AnyError {
+#[derive(Debug, thiserror::Error)]
+pub enum NetError {
+  #[error("Listener has been closed")]
+  ListenerClosed,
+  #[error("Listener already in use")]
+  ListenerBusy,
+  #[error("Socket has been closed")]
+  SocketClosed,
+  #[error("Socket has been closed")]
+  SocketClosedNotConnected,
+  #[error("Socket already in use")]
+  SocketBusy,
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error("Another accept task is ongoing")]
+  AcceptTaskOngoing,
+  #[error("{0}")]
+  Permission(deno_core::error::AnyError),
+  #[error("{0}")]
+  Resource(deno_core::error::AnyError),
+  #[error("No resolved address found")]
+  NoResolvedAddress,
+  #[error("{0}")]
+  AddrParse(#[from] std::net::AddrParseError),
+  #[error("{0}")]
+  Map(crate::io::MapError),
+  #[error("{0}")]
+  Canceled(#[from] deno_core::Canceled),
+  #[error("{0}")]
+  DnsNotFound(ResolveError),
+  #[error("{0}")]
+  DnsNotConnected(ResolveError),
+  #[error("{0}")]
+  DnsTimedOut(ResolveError),
+  #[error("{0}")]
+  Dns(#[from] ResolveError),
+  #[error("Provided record type is not supported")]
+  UnsupportedRecordType,
+  #[error("File name or path {0:?} is not valid UTF-8")]
+  InvalidUtf8(std::ffi::OsString),
+  #[error("unexpected key type")]
+  UnexpectedKeyType,
+  #[error("Invalid hostname: '{0}'")]
+  InvalidHostname(String), // TypeError
+  #[error("TCP stream is currently in use")]
+  TcpStreamBusy,
+  #[error("{0}")]
+  Rustls(#[from] deno_tls::rustls::Error),
+  #[error("{0}")]
+  Tls(#[from] deno_tls::TlsError),
+  #[error("Error creating TLS certificate: Deno.listenTls requires a key")]
+  ListenTlsRequiresKey, // InvalidData
+  #[error("{0}")]
+  RootCertStore(deno_core::anyhow::Error),
+  #[error("{0}")]
+  Reunite(tokio::net::tcp::ReuniteError),
+}
+
+pub(crate) fn accept_err(e: std::io::Error) -> NetError {
   if let std::io::ErrorKind::Interrupted = e.kind() {
-    bad_resource("Listener has been closed")
+    NetError::ListenerClosed
   } else {
-    e.into()
+    NetError::Io(e)
   }
 }
 
@@ -81,15 +136,15 @@ pub(crate) fn accept_err(e: std::io::Error) -> AnyError {
 pub async fn op_net_accept_tcp(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError> {
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<NetworkListenerResource<TcpListener>>(rid)
-    .map_err(|_| bad_resource("Listener has been closed"))?;
+    .map_err(|_| NetError::ListenerClosed)?;
   let listener = RcRef::map(&resource, |r| &r.listener)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Another accept task is ongoing"))?;
+    .ok_or_else(|| NetError::AcceptTaskOngoing)?;
   let cancel = RcRef::map(resource, |r| &r.cancel);
   let (tcp_stream, _socket_addr) = listener
     .accept()
@@ -112,12 +167,12 @@ pub async fn op_net_recv_udp(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[buffer] mut buf: JsBuffer,
-) -> Result<(usize, IpAddr), AnyError> {
+) -> Result<(usize, IpAddr), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
   let cancel_handle = RcRef::map(&resource, |r| &r.cancel);
   let (nread, remote_addr) = socket
@@ -134,27 +189,29 @@ pub async fn op_net_send_udp<NP>(
   #[smi] rid: ResourceId,
   #[serde] addr: IpAddr,
   #[buffer] zero_copy: JsBuffer,
-) -> Result<usize, AnyError>
+) -> Result<usize, NetError>
 where
   NP: NetPermissions + 'static,
 {
   {
     let mut s = state.borrow_mut();
-    s.borrow_mut::<NP>().check_net(
-      &(&addr.hostname, Some(addr.port)),
-      "Deno.DatagramConn.send()",
-    )?;
+    s.borrow_mut::<NP>()
+      .check_net(
+        &(&addr.hostname, Some(addr.port)),
+        "Deno.DatagramConn.send()",
+      )
+      .map_err(NetError::Permission)?;
   }
   let addr = resolve_addr(&addr.hostname, addr.port)
     .await?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or(NetError::NoResolvedAddress)?;
 
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
   let nwritten = socket.send_to(&zero_copy, &addr).await?;
 
@@ -167,12 +224,12 @@ pub async fn op_net_join_multi_v4_udp(
   #[smi] rid: ResourceId,
   #[string] address: String,
   #[string] multi_interface: String,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   let addr = Ipv4Addr::from_str(address.as_str())?;
@@ -189,12 +246,12 @@ pub async fn op_net_join_multi_v6_udp(
   #[smi] rid: ResourceId,
   #[string] address: String,
   #[smi] multi_interface: u32,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   let addr = Ipv6Addr::from_str(address.as_str())?;
@@ -210,12 +267,12 @@ pub async fn op_net_leave_multi_v4_udp(
   #[smi] rid: ResourceId,
   #[string] address: String,
   #[string] multi_interface: String,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   let addr = Ipv4Addr::from_str(address.as_str())?;
@@ -232,12 +289,12 @@ pub async fn op_net_leave_multi_v6_udp(
   #[smi] rid: ResourceId,
   #[string] address: String,
   #[smi] multi_interface: u32,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   let addr = Ipv6Addr::from_str(address.as_str())?;
@@ -253,16 +310,16 @@ pub async fn op_net_set_multi_loopback_udp(
   #[smi] rid: ResourceId,
   is_v4_membership: bool,
   loopback: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   if is_v4_membership {
-    socket.set_multicast_loop_v4(loopback)?
+    socket.set_multicast_loop_v4(loopback)?;
   } else {
     socket.set_multicast_loop_v6(loopback)?;
   }
@@ -275,12 +332,12 @@ pub async fn op_net_set_multi_ttl_udp(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[smi] ttl: u32,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let resource = state
     .borrow_mut()
     .resource_table
     .get::<UdpSocketResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket).borrow().await;
 
   socket.set_multicast_ttl_v4(ttl)?;
@@ -293,7 +350,7 @@ pub async fn op_net_set_multi_ttl_udp(
 pub async fn op_net_connect_tcp<NP>(
   state: Rc<RefCell<OpState>>,
   #[serde] addr: IpAddr,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -304,7 +361,7 @@ where
 pub async fn op_net_connect_tcp_inner<NP>(
   state: Rc<RefCell<OpState>>,
   addr: IpAddr,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -312,13 +369,14 @@ where
     let mut state_ = state.borrow_mut();
     state_
       .borrow_mut::<NP>()
-      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.connect()")?;
+      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.connect()")
+      .map_err(NetError::Permission)?;
   }
 
   let addr = resolve_addr(&addr.hostname, addr.port)
     .await?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or_else(|| NetError::NoResolvedAddress)?;
   let tcp_stream = TcpStream::connect(&addr).await?;
   let local_addr = tcp_stream.local_addr()?;
   let remote_addr = tcp_stream.peer_addr()?;
@@ -353,7 +411,7 @@ pub fn op_net_listen_tcp<NP>(
   #[serde] addr: IpAddr,
   reuse_port: bool,
   load_balanced: bool,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -362,10 +420,11 @@ where
   }
   state
     .borrow_mut::<NP>()
-    .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listen()")?;
+    .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listen()")
+    .map_err(NetError::Permission)?;
   let addr = resolve_addr_sync(&addr.hostname, addr.port)?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or_else(|| NetError::NoResolvedAddress)?;
 
   let listener = if load_balanced {
     TcpListener::bind_load_balanced(addr)
@@ -384,16 +443,17 @@ fn net_listen_udp<NP>(
   addr: IpAddr,
   reuse_address: bool,
   loopback: bool,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
   state
     .borrow_mut::<NP>()
-    .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listenDatagram()")?;
+    .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listenDatagram()")
+    .map_err(NetError::Permission)?;
   let addr = resolve_addr_sync(&addr.hostname, addr.port)?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or_else(|| NetError::NoResolvedAddress)?;
 
   let domain = if addr.is_ipv4() {
     Domain::IPV4
@@ -453,7 +513,7 @@ pub fn op_net_listen_udp<NP>(
   #[serde] addr: IpAddr,
   reuse_address: bool,
   loopback: bool,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -468,7 +528,7 @@ pub fn op_node_unstable_net_listen_udp<NP>(
   #[serde] addr: IpAddr,
   reuse_address: bool,
   loopback: bool,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -551,7 +611,7 @@ pub struct NameServer {
 pub async fn op_dns_resolve<NP>(
   state: Rc<RefCell<OpState>>,
   #[serde] args: ResolveAddrArgs,
-) -> Result<Vec<DnsReturnRecord>, AnyError>
+) -> Result<Vec<DnsReturnRecord>, NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -587,7 +647,9 @@ where
       let socker_addr = &ns.socket_addr;
       let ip = socker_addr.ip().to_string();
       let port = socker_addr.port();
-      perm.check_net(&(ip, Some(port)), "Deno.resolveDns()")?;
+      perm
+        .check_net(&(ip, Some(port)), "Deno.resolveDns()")
+        .map_err(NetError::Permission)?;
     }
   }
 
@@ -618,22 +680,17 @@ where
   };
 
   lookup
-    .map_err(|e| {
-      let message = format!("{e}");
-      match e.kind() {
-        ResolveErrorKind::NoRecordsFound { .. } => {
-          custom_error("NotFound", message)
-        }
-        ResolveErrorKind::Message("No connections available") => {
-          custom_error("NotConnected", message)
-        }
-        ResolveErrorKind::Timeout => custom_error("TimedOut", message),
-        _ => generic_error(message),
+    .map_err(|e| match e.kind() {
+      ResolveErrorKind::NoRecordsFound { .. } => NetError::DnsNotFound(e),
+      ResolveErrorKind::Message("No connections available") => {
+        NetError::DnsNotConnected(e)
       }
+      ResolveErrorKind::Timeout => NetError::DnsTimedOut(e),
+      _ => NetError::Dns(e),
     })?
     .iter()
     .filter_map(|rdata| rdata_to_return_record(record_type)(rdata).transpose())
-    .collect::<Result<Vec<DnsReturnRecord>, AnyError>>()
+    .collect::<Result<Vec<DnsReturnRecord>, NetError>>()
 }
 
 #[op2(fast)]
@@ -641,7 +698,7 @@ pub fn op_set_nodelay(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   nodelay: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   op_set_nodelay_inner(state, rid, nodelay)
 }
 
@@ -650,10 +707,12 @@ pub fn op_set_nodelay_inner(
   state: &mut OpState,
   rid: ResourceId,
   nodelay: bool,
-) -> Result<(), AnyError> {
-  let resource: Rc<TcpStreamResource> =
-    state.resource_table.get::<TcpStreamResource>(rid)?;
-  resource.set_nodelay(nodelay)
+) -> Result<(), NetError> {
+  let resource: Rc<TcpStreamResource> = state
+    .resource_table
+    .get::<TcpStreamResource>(rid)
+    .map_err(NetError::Resource)?;
+  resource.set_nodelay(nodelay).map_err(NetError::Map)
 }
 
 #[op2(fast)]
@@ -661,7 +720,7 @@ pub fn op_set_keepalive(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   keepalive: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   op_set_keepalive_inner(state, rid, keepalive)
 }
 
@@ -670,17 +729,19 @@ pub fn op_set_keepalive_inner(
   state: &mut OpState,
   rid: ResourceId,
   keepalive: bool,
-) -> Result<(), AnyError> {
-  let resource: Rc<TcpStreamResource> =
-    state.resource_table.get::<TcpStreamResource>(rid)?;
-  resource.set_keepalive(keepalive)
+) -> Result<(), NetError> {
+  let resource: Rc<TcpStreamResource> = state
+    .resource_table
+    .get::<TcpStreamResource>(rid)
+    .map_err(NetError::Resource)?;
+  resource.set_keepalive(keepalive).map_err(NetError::Map)
 }
 
 fn rdata_to_return_record(
   ty: RecordType,
-) -> impl Fn(&RData) -> Result<Option<DnsReturnRecord>, AnyError> {
+) -> impl Fn(&RData) -> Result<Option<DnsReturnRecord>, NetError> {
   use RecordType::*;
-  move |r: &RData| -> Result<Option<DnsReturnRecord>, AnyError> {
+  move |r: &RData| -> Result<Option<DnsReturnRecord>, NetError> {
     let record = match ty {
       A => r.as_a().map(ToString::to_string).map(DnsReturnRecord::A),
       AAAA => r
@@ -761,12 +822,7 @@ fn rdata_to_return_record(
           .collect();
         DnsReturnRecord::Txt(texts)
       }),
-      _ => {
-        return Err(custom_error(
-          "NotSupported",
-          "Provided record type is not supported",
-        ))
-      }
+      _ => return Err(NetError::UnsupportedRecordType),
     };
     Ok(record)
   }
@@ -985,7 +1041,7 @@ mod tests {
       &mut self,
       _host: &(T, Option<u16>),
       _api_name: &str,
-    ) -> Result<(), AnyError> {
+    ) -> Result<(), deno_core::error::AnyError> {
       Ok(())
     }
 
@@ -993,7 +1049,7 @@ mod tests {
       &mut self,
       p: &str,
       _api_name: &str,
-    ) -> Result<PathBuf, AnyError> {
+    ) -> Result<PathBuf, deno_core::error::AnyError> {
       Ok(PathBuf::from(p))
     }
 
@@ -1001,7 +1057,7 @@ mod tests {
       &mut self,
       p: &str,
       _api_name: &str,
-    ) -> Result<PathBuf, AnyError> {
+    ) -> Result<PathBuf, deno_core::error::AnyError> {
       Ok(PathBuf::from(p))
     }
 
@@ -1009,7 +1065,7 @@ mod tests {
       &mut self,
       p: &'a Path,
       _api_name: &str,
-    ) -> Result<Cow<'a, Path>, AnyError> {
+    ) -> Result<Cow<'a, Path>, deno_core::error::AnyError> {
       Ok(Cow::Borrowed(p))
     }
   }
@@ -1091,7 +1147,7 @@ mod tests {
         let vals = result.unwrap();
         rid = rid.or(Some(vals.0));
       }
-    };
+    }
     let rid = rid.unwrap();
 
     let state = runtime.op_state();
diff --git a/ext/net/ops_tls.rs b/ext/net/ops_tls.rs
index 5bc04ceb51..c7d65dd85e 100644
--- a/ext/net/ops_tls.rs
+++ b/ext/net/ops_tls.rs
@@ -2,6 +2,7 @@
 
 use crate::io::TcpStreamResource;
 use crate::ops::IpAddr;
+use crate::ops::NetError;
 use crate::ops::TlsHandshakeInfo;
 use crate::raw::NetworkListenerResource;
 use crate::resolve_addr::resolve_addr;
@@ -10,13 +11,7 @@ use crate::tcp::TcpListener;
 use crate::DefaultTlsOptions;
 use crate::NetPermissions;
 use crate::UnsafelyIgnoreCertificateErrors;
-use deno_core::anyhow::anyhow;
-use deno_core::anyhow::bail;
-use deno_core::error::bad_resource;
-use deno_core::error::custom_error;
-use deno_core::error::generic_error;
-use deno_core::error::invalid_hostname;
-use deno_core::error::AnyError;
+use deno_core::futures::TryFutureExt;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::AsyncRefCell;
@@ -118,20 +113,23 @@ impl TlsStreamResource {
   pub async fn read(
     self: Rc<Self>,
     data: &mut [u8],
-  ) -> Result<usize, AnyError> {
+  ) -> Result<usize, std::io::Error> {
     let mut rd = RcRef::map(&self, |r| &r.rd).borrow_mut().await;
     let cancel_handle = RcRef::map(&self, |r| &r.cancel_handle);
-    Ok(rd.read(data).try_or_cancel(cancel_handle).await?)
+    rd.read(data).try_or_cancel(cancel_handle).await
   }
 
-  pub async fn write(self: Rc<Self>, data: &[u8]) -> Result<usize, AnyError> {
+  pub async fn write(
+    self: Rc<Self>,
+    data: &[u8],
+  ) -> Result<usize, std::io::Error> {
     let mut wr = RcRef::map(self, |r| &r.wr).borrow_mut().await;
     let nwritten = wr.write(data).await?;
     wr.flush().await?;
     Ok(nwritten)
   }
 
-  pub async fn shutdown(self: Rc<Self>) -> Result<(), AnyError> {
+  pub async fn shutdown(self: Rc<Self>) -> Result<(), std::io::Error> {
     let mut wr = RcRef::map(self, |r| &r.wr).borrow_mut().await;
     wr.shutdown().await?;
     Ok(())
@@ -139,7 +137,7 @@ impl TlsStreamResource {
 
   pub async fn handshake(
     self: &Rc<Self>,
-  ) -> Result<TlsHandshakeInfo, AnyError> {
+  ) -> Result<TlsHandshakeInfo, std::io::Error> {
     if let Some(tls_info) = &*self.handshake_info.borrow() {
       return Ok(tls_info.clone());
     }
@@ -164,7 +162,7 @@ impl Resource for TlsStreamResource {
   }
 
   fn shutdown(self: Rc<Self>) -> AsyncResult<()> {
-    Box::pin(self.shutdown())
+    Box::pin(self.shutdown().map_err(Into::into))
   }
 
   fn close(self: Rc<Self>) {
@@ -201,7 +199,7 @@ pub fn op_tls_key_null() -> TlsKeysHolder {
 pub fn op_tls_key_static(
   #[string] cert: &str,
   #[string] key: &str,
-) -> Result<TlsKeysHolder, AnyError> {
+) -> Result<TlsKeysHolder, deno_tls::TlsError> {
   let cert = load_certs(&mut BufReader::new(cert.as_bytes()))?;
   let key = load_private_keys(key.as_bytes())?
     .into_iter()
@@ -236,9 +234,9 @@ pub fn op_tls_cert_resolver_resolve(
   #[cppgc] lookup: &TlsKeyLookup,
   #[string] sni: String,
   #[cppgc] key: &TlsKeysHolder,
-) -> Result<(), AnyError> {
+) -> Result<(), NetError> {
   let TlsKeys::Static(key) = key.take() else {
-    bail!("unexpected key type");
+    return Err(NetError::UnexpectedKeyType);
   };
   lookup.resolve(sni, Ok(key));
   Ok(())
@@ -250,7 +248,7 @@ pub fn op_tls_cert_resolver_resolve_error(
   #[string] sni: String,
   #[string] error: String,
 ) {
-  lookup.resolve(sni, Err(anyhow!(error)))
+  lookup.resolve(sni, Err(error))
 }
 
 #[op2]
@@ -258,7 +256,7 @@ pub fn op_tls_cert_resolver_resolve_error(
 pub fn op_tls_start<NP>(
   state: Rc<RefCell<OpState>>,
   #[serde] args: StartTlsArgs,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -271,7 +269,9 @@ where
   {
     let mut s = state.borrow_mut();
     let permissions = s.borrow_mut::<NP>();
-    permissions.check_net(&(&hostname, Some(0)), "Deno.startTls()")?;
+    permissions
+      .check_net(&(&hostname, Some(0)), "Deno.startTls()")
+      .map_err(NetError::Permission)?;
   }
 
   let ca_certs = args
@@ -281,7 +281,7 @@ where
     .collect::<Vec<_>>();
 
   let hostname_dns = ServerName::try_from(hostname.to_string())
-    .map_err(|_| invalid_hostname(&hostname))?;
+    .map_err(|_| NetError::InvalidHostname(hostname))?;
 
   let unsafely_ignore_certificate_errors = state
     .borrow()
@@ -291,19 +291,21 @@ where
   let root_cert_store = state
     .borrow()
     .borrow::<DefaultTlsOptions>()
-    .root_cert_store()?;
+    .root_cert_store()
+    .map_err(NetError::RootCertStore)?;
 
   let resource_rc = state
     .borrow_mut()
     .resource_table
-    .take::<TcpStreamResource>(rid)?;
+    .take::<TcpStreamResource>(rid)
+    .map_err(NetError::Resource)?;
   // This TCP connection might be used somewhere else. If it's the case, we cannot proceed with the
   // process of starting a TLS connection on top of this TCP connection, so we just return a Busy error.
   // See also: https://github.com/denoland/deno/pull/16242
-  let resource = Rc::try_unwrap(resource_rc)
-    .map_err(|_| custom_error("Busy", "TCP stream is currently in use"))?;
+  let resource =
+    Rc::try_unwrap(resource_rc).map_err(|_| NetError::TcpStreamBusy)?;
   let (read_half, write_half) = resource.into_inner();
-  let tcp_stream = read_half.reunite(write_half)?;
+  let tcp_stream = read_half.reunite(write_half).map_err(NetError::Reunite)?;
 
   let local_addr = tcp_stream.local_addr()?;
   let remote_addr = tcp_stream.peer_addr()?;
@@ -345,7 +347,7 @@ pub async fn op_net_connect_tls<NP>(
   #[serde] addr: IpAddr,
   #[serde] args: ConnectTlsArgs,
   #[cppgc] key_pair: &TlsKeysHolder,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -359,9 +361,14 @@ where
     let mut s = state.borrow_mut();
     let permissions = s.borrow_mut::<NP>();
     permissions
-      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.connectTls()")?;
+      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.connectTls()")
+      .map_err(NetError::Permission)?;
     if let Some(path) = cert_file {
-      Some(permissions.check_read(path, "Deno.connectTls()")?)
+      Some(
+        permissions
+          .check_read(path, "Deno.connectTls()")
+          .map_err(NetError::Permission)?,
+      )
     } else {
       None
     }
@@ -382,17 +389,18 @@ where
   let root_cert_store = state
     .borrow()
     .borrow::<DefaultTlsOptions>()
-    .root_cert_store()?;
+    .root_cert_store()
+    .map_err(NetError::RootCertStore)?;
   let hostname_dns = if let Some(server_name) = args.server_name {
     ServerName::try_from(server_name)
   } else {
     ServerName::try_from(addr.hostname.clone())
   }
-  .map_err(|_| invalid_hostname(&addr.hostname))?;
+  .map_err(|_| NetError::InvalidHostname(addr.hostname.clone()))?;
   let connect_addr = resolve_addr(&addr.hostname, addr.port)
     .await?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or_else(|| NetError::NoResolvedAddress)?;
   let tcp_stream = TcpStream::connect(connect_addr).await?;
   let local_addr = tcp_stream.local_addr()?;
   let remote_addr = tcp_stream.peer_addr()?;
@@ -444,7 +452,7 @@ pub fn op_net_listen_tls<NP>(
   #[serde] addr: IpAddr,
   #[serde] args: ListenTlsArgs,
   #[cppgc] keys: &TlsKeysHolder,
-) -> Result<(ResourceId, IpAddr), AnyError>
+) -> Result<(ResourceId, IpAddr), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -455,12 +463,13 @@ where
   {
     let permissions = state.borrow_mut::<NP>();
     permissions
-      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listenTls()")?;
+      .check_net(&(&addr.hostname, Some(addr.port)), "Deno.listenTls()")
+      .map_err(NetError::Permission)?;
   }
 
   let bind_addr = resolve_addr_sync(&addr.hostname, addr.port)?
     .next()
-    .ok_or_else(|| generic_error("No resolved address found"))?;
+    .ok_or(NetError::NoResolvedAddress)?;
 
   let tcp_listener = if args.load_balanced {
     TcpListener::bind_load_balanced(bind_addr)
@@ -475,28 +484,24 @@ where
     .map(|s| s.into_bytes())
     .collect();
   let listener = match keys.take() {
-    TlsKeys::Null => Err(anyhow!("Deno.listenTls requires a key")),
+    TlsKeys::Null => return Err(NetError::ListenTlsRequiresKey),
     TlsKeys::Static(TlsKey(cert, key)) => {
       let mut tls_config = ServerConfig::builder()
         .with_no_client_auth()
-        .with_single_cert(cert, key)
-        .map_err(|e| anyhow!(e))?;
+        .with_single_cert(cert, key)?;
       tls_config.alpn_protocols = alpn;
-      Ok(TlsListener {
+      TlsListener {
         tcp_listener,
         tls_config: Some(tls_config.into()),
         server_config_provider: None,
-      })
+      }
     }
-    TlsKeys::Resolver(resolver) => Ok(TlsListener {
+    TlsKeys::Resolver(resolver) => TlsListener {
       tcp_listener,
       tls_config: None,
       server_config_provider: Some(resolver.into_server_config_provider(alpn)),
-    }),
-  }
-  .map_err(|e| {
-    custom_error("InvalidData", "Error creating TLS certificate").context(e)
-  })?;
+    },
+  };
 
   let tls_listener_resource = NetworkListenerResource::new(listener);
 
@@ -510,23 +515,23 @@ where
 pub async fn op_net_accept_tls(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(ResourceId, IpAddr, IpAddr), AnyError> {
+) -> Result<(ResourceId, IpAddr, IpAddr), NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<NetworkListenerResource<TlsListener>>(rid)
-    .map_err(|_| bad_resource("Listener has been closed"))?;
+    .map_err(|_| NetError::ListenerClosed)?;
 
   let cancel_handle = RcRef::map(&resource, |r| &r.cancel);
   let listener = RcRef::map(&resource, |r| &r.listener)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Another accept task is ongoing"))?;
+    .ok_or_else(|| NetError::AcceptTaskOngoing)?;
 
   let (tls_stream, remote_addr) =
     match listener.accept().try_or_cancel(&cancel_handle).await {
       Ok(tuple) => tuple,
       Err(err) if err.kind() == ErrorKind::Interrupted => {
-        return Err(bad_resource("Listener has been closed"));
+        return Err(NetError::ListenerClosed);
       }
       Err(err) => return Err(err.into()),
     };
@@ -547,11 +552,11 @@ pub async fn op_net_accept_tls(
 pub async fn op_tls_handshake(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<TlsHandshakeInfo, AnyError> {
+) -> Result<TlsHandshakeInfo, NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<TlsStreamResource>(rid)
-    .map_err(|_| bad_resource("Listener has been closed"))?;
-  resource.handshake().await
+    .map_err(|_| NetError::ListenerClosed)?;
+  resource.handshake().await.map_err(Into::into)
 }
diff --git a/ext/net/ops_unix.rs b/ext/net/ops_unix.rs
index 95293284f0..04ae84906f 100644
--- a/ext/net/ops_unix.rs
+++ b/ext/net/ops_unix.rs
@@ -1,11 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use crate::io::UnixStreamResource;
+use crate::ops::NetError;
 use crate::raw::NetworkListenerResource;
 use crate::NetPermissions;
-use deno_core::error::bad_resource;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::AsyncRefCell;
 use deno_core::CancelHandle;
@@ -26,11 +24,8 @@ use tokio::net::UnixListener;
 pub use tokio::net::UnixStream;
 
 /// A utility function to map OsStrings to Strings
-pub fn into_string(s: std::ffi::OsString) -> Result<String, AnyError> {
-  s.into_string().map_err(|s| {
-    let message = format!("File name or path {s:?} is not valid UTF-8");
-    custom_error("InvalidData", message)
-  })
+pub fn into_string(s: std::ffi::OsString) -> Result<String, NetError> {
+  s.into_string().map_err(NetError::InvalidUtf8)
 }
 
 pub struct UnixDatagramResource {
@@ -63,15 +58,15 @@ pub struct UnixListenArgs {
 pub async fn op_net_accept_unix(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(ResourceId, Option<String>, Option<String>), AnyError> {
+) -> Result<(ResourceId, Option<String>, Option<String>), NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<NetworkListenerResource<UnixListener>>(rid)
-    .map_err(|_| bad_resource("Listener has been closed"))?;
+    .map_err(|_| NetError::ListenerClosed)?;
   let listener = RcRef::map(&resource, |r| &r.listener)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Listener already in use"))?;
+    .ok_or(NetError::ListenerBusy)?;
   let cancel = RcRef::map(resource, |r| &r.cancel);
   let (unix_stream, _socket_addr) = listener
     .accept()
@@ -95,7 +90,7 @@ pub async fn op_net_accept_unix(
 pub async fn op_net_connect_unix<NP>(
   state: Rc<RefCell<OpState>>,
   #[string] address_path: String,
-) -> Result<(ResourceId, Option<String>, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -103,10 +98,12 @@ where
     let mut state_ = state.borrow_mut();
     let address_path = state_
       .borrow_mut::<NP>()
-      .check_read(&address_path, "Deno.connect()")?;
+      .check_read(&address_path, "Deno.connect()")
+      .map_err(NetError::Permission)?;
     _ = state_
       .borrow_mut::<NP>()
-      .check_write_path(&address_path, "Deno.connect()")?;
+      .check_write_path(&address_path, "Deno.connect()")
+      .map_err(NetError::Permission)?;
     address_path
   };
   let unix_stream = UnixStream::connect(&address_path).await?;
@@ -127,15 +124,15 @@ pub async fn op_net_recv_unixpacket(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[buffer] mut buf: JsBuffer,
-) -> Result<(usize, Option<String>), AnyError> {
+) -> Result<(usize, Option<String>), NetError> {
   let resource = state
     .borrow()
     .resource_table
     .get::<UnixDatagramResource>(rid)
-    .map_err(|_| bad_resource("Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosed)?;
   let socket = RcRef::map(&resource, |r| &r.socket)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Socket already in use"))?;
+    .ok_or(NetError::SocketBusy)?;
   let cancel = RcRef::map(resource, |r| &r.cancel);
   let (nread, remote_addr) =
     socket.recv_from(&mut buf).try_or_cancel(cancel).await?;
@@ -150,24 +147,25 @@ pub async fn op_net_send_unixpacket<NP>(
   #[smi] rid: ResourceId,
   #[string] address_path: String,
   #[buffer] zero_copy: JsBuffer,
-) -> Result<usize, AnyError>
+) -> Result<usize, NetError>
 where
   NP: NetPermissions + 'static,
 {
   let address_path = {
     let mut s = state.borrow_mut();
     s.borrow_mut::<NP>()
-      .check_write(&address_path, "Deno.DatagramConn.send()")?
+      .check_write(&address_path, "Deno.DatagramConn.send()")
+      .map_err(NetError::Permission)?
   };
 
   let resource = state
     .borrow()
     .resource_table
     .get::<UnixDatagramResource>(rid)
-    .map_err(|_| custom_error("NotConnected", "Socket has been closed"))?;
+    .map_err(|_| NetError::SocketClosedNotConnected)?;
   let socket = RcRef::map(&resource, |r| &r.socket)
     .try_borrow_mut()
-    .ok_or_else(|| custom_error("Busy", "Socket already in use"))?;
+    .ok_or(NetError::SocketBusy)?;
   let nwritten = socket.send_to(&zero_copy, address_path).await?;
 
   Ok(nwritten)
@@ -179,14 +177,18 @@ pub fn op_net_listen_unix<NP>(
   state: &mut OpState,
   #[string] address_path: String,
   #[string] api_name: String,
-) -> Result<(ResourceId, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
   let permissions = state.borrow_mut::<NP>();
   let api_call_expr = format!("{}()", api_name);
-  let address_path = permissions.check_read(&address_path, &api_call_expr)?;
-  _ = permissions.check_write_path(&address_path, &api_call_expr)?;
+  let address_path = permissions
+    .check_read(&address_path, &api_call_expr)
+    .map_err(NetError::Permission)?;
+  _ = permissions
+    .check_write_path(&address_path, &api_call_expr)
+    .map_err(NetError::Permission)?;
   let listener = UnixListener::bind(address_path)?;
   let local_addr = listener.local_addr()?;
   let pathname = local_addr.as_pathname().map(pathstring).transpose()?;
@@ -198,14 +200,17 @@ where
 pub fn net_listen_unixpacket<NP>(
   state: &mut OpState,
   address_path: String,
-) -> Result<(ResourceId, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
   let permissions = state.borrow_mut::<NP>();
-  let address_path =
-    permissions.check_read(&address_path, "Deno.listenDatagram()")?;
-  _ = permissions.check_write_path(&address_path, "Deno.listenDatagram()")?;
+  let address_path = permissions
+    .check_read(&address_path, "Deno.listenDatagram()")
+    .map_err(NetError::Permission)?;
+  _ = permissions
+    .check_write_path(&address_path, "Deno.listenDatagram()")
+    .map_err(NetError::Permission)?;
   let socket = UnixDatagram::bind(address_path)?;
   let local_addr = socket.local_addr()?;
   let pathname = local_addr.as_pathname().map(pathstring).transpose()?;
@@ -222,7 +227,7 @@ where
 pub fn op_net_listen_unixpacket<NP>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<(ResourceId, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
@@ -235,13 +240,13 @@ where
 pub fn op_node_unstable_net_listen_unixpacket<NP>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<(ResourceId, Option<String>), AnyError>
+) -> Result<(ResourceId, Option<String>), NetError>
 where
   NP: NetPermissions + 'static,
 {
   net_listen_unixpacket::<NP>(state, path)
 }
 
-pub fn pathstring(pathname: &Path) -> Result<String, AnyError> {
+pub fn pathstring(pathname: &Path) -> Result<String, NetError> {
   into_string(pathname.into())
 }
diff --git a/ext/net/resolve_addr.rs b/ext/net/resolve_addr.rs
index 8bbdd5192c..3a97081eac 100644
--- a/ext/net/resolve_addr.rs
+++ b/ext/net/resolve_addr.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use std::net::SocketAddr;
 use std::net::ToSocketAddrs;
 use tokio::net::lookup_host;
@@ -9,7 +8,7 @@ use tokio::net::lookup_host;
 pub async fn resolve_addr(
   hostname: &str,
   port: u16,
-) -> Result<impl Iterator<Item = SocketAddr> + '_, AnyError> {
+) -> Result<impl Iterator<Item = SocketAddr> + '_, std::io::Error> {
   let addr_port_pair = make_addr_port_pair(hostname, port);
   let result = lookup_host(addr_port_pair).await?;
   Ok(result)
@@ -19,7 +18,7 @@ pub async fn resolve_addr(
 pub fn resolve_addr_sync(
   hostname: &str,
   port: u16,
-) -> Result<impl Iterator<Item = SocketAddr>, AnyError> {
+) -> Result<impl Iterator<Item = SocketAddr>, std::io::Error> {
   let addr_port_pair = make_addr_port_pair(hostname, port);
   let result = addr_port_pair.to_socket_addrs()?;
   Ok(result)
diff --git a/ext/node/Cargo.toml b/ext/node/Cargo.toml
index c5f07210b2..ed31dbf17e 100644
--- a/ext/node/Cargo.toml
+++ b/ext/node/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_node"
-version = "0.108.0"
+version = "0.112.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/node/lib.rs b/ext/node/lib.rs
index 03462f36fa..db6d08e11e 100644
--- a/ext/node/lib.rs
+++ b/ext/node/lib.rs
@@ -9,22 +9,18 @@ use std::path::Path;
 use std::path::PathBuf;
 
 use deno_core::error::AnyError;
-use deno_core::located_script_name;
 use deno_core::op2;
 use deno_core::url::Url;
 #[allow(unused_imports)]
 use deno_core::v8;
 use deno_core::v8::ExternalReference;
-use deno_core::JsRuntime;
-use deno_fs::sync::MaybeSend;
-use deno_fs::sync::MaybeSync;
 use node_resolver::NpmResolverRc;
 use once_cell::sync::Lazy;
 
 extern crate libz_sys as zlib;
 
 mod global;
-mod ops;
+pub mod ops;
 mod polyfill;
 
 pub use deno_package_json::PackageJson;
@@ -125,16 +121,17 @@ impl NodePermissions for deno_permissions::PermissionsContainer {
 }
 
 #[allow(clippy::disallowed_types)]
-pub type NodeRequireResolverRc =
-  deno_fs::sync::MaybeArc<dyn NodeRequireResolver>;
+pub type NodeRequireLoaderRc = std::rc::Rc<dyn NodeRequireLoader>;
 
-pub trait NodeRequireResolver: std::fmt::Debug + MaybeSend + MaybeSync {
+pub trait NodeRequireLoader {
   #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
   fn ensure_read_permission<'a>(
     &self,
     permissions: &mut dyn NodePermissions,
     path: &'a Path,
   ) -> Result<Cow<'a, Path>, AnyError>;
+
+  fn load_text_file_lossy(&self, path: &Path) -> Result<String, AnyError>;
 }
 
 pub static NODE_ENV_VAR_ALLOWLIST: Lazy<HashSet<String>> = Lazy::new(|| {
@@ -152,10 +149,12 @@ fn op_node_build_os() -> String {
   env!("TARGET").split('-').nth(2).unwrap().to_string()
 }
 
+#[derive(Clone)]
 pub struct NodeExtInitServices {
-  pub node_require_resolver: NodeRequireResolverRc,
+  pub node_require_loader: NodeRequireLoaderRc,
   pub node_resolver: NodeResolverRc,
   pub npm_resolver: NpmResolverRc,
+  pub pkg_json_resolver: PackageJsonResolverRc,
 }
 
 deno_core::extension!(deno_node,
@@ -348,7 +347,7 @@ deno_core::extension!(deno_node,
     ops::http2::op_http2_send_response,
     ops::os::op_node_os_get_priority<P>,
     ops::os::op_node_os_set_priority<P>,
-    ops::os::op_node_os_username<P>,
+    ops::os::op_node_os_user_info<P>,
     ops::os::op_geteuid<P>,
     ops::os::op_getegid<P>,
     ops::os::op_cpus<P>,
@@ -469,6 +468,7 @@ deno_core::extension!(deno_node,
     "internal_binding/constants.ts",
     "internal_binding/crypto.ts",
     "internal_binding/handle_wrap.ts",
+    "internal_binding/http_parser.ts",
     "internal_binding/mod.ts",
     "internal_binding/node_file.ts",
     "internal_binding/node_options.ts",
@@ -638,9 +638,10 @@ deno_core::extension!(deno_node,
     state.put(options.fs.clone());
 
     if let Some(init) = &options.maybe_init {
-      state.put(init.node_require_resolver.clone());
+      state.put(init.node_require_loader.clone());
       state.put(init.node_resolver.clone());
       state.put(init.npm_resolver.clone());
+      state.put(init.pkg_json_resolver.clone());
     }
   },
   global_template_middleware = global_template_middleware,
@@ -760,33 +761,16 @@ deno_core::extension!(deno_node,
   },
 );
 
-pub fn load_cjs_module(
-  js_runtime: &mut JsRuntime,
-  module: &str,
-  main: bool,
-  inspect_brk: bool,
-) -> Result<(), AnyError> {
-  fn escape_for_single_quote_string(text: &str) -> String {
-    text.replace('\\', r"\\").replace('\'', r"\'")
-  }
-
-  let source_code = format!(
-    r#"(function loadCjsModule(moduleName, isMain, inspectBrk) {{
-      Deno[Deno.internal].node.loadCjsModule(moduleName, isMain, inspectBrk);
-    }})('{module}', {main}, {inspect_brk});"#,
-    main = main,
-    module = escape_for_single_quote_string(module),
-    inspect_brk = inspect_brk,
-  );
-
-  js_runtime.execute_script(located_script_name!(), source_code)?;
-  Ok(())
-}
-
 pub type NodeResolver = node_resolver::NodeResolver<DenoFsNodeResolverEnv>;
 #[allow(clippy::disallowed_types)]
 pub type NodeResolverRc =
   deno_fs::sync::MaybeArc<node_resolver::NodeResolver<DenoFsNodeResolverEnv>>;
+pub type PackageJsonResolver =
+  node_resolver::PackageJsonResolver<DenoFsNodeResolverEnv>;
+#[allow(clippy::disallowed_types)]
+pub type PackageJsonResolverRc = deno_fs::sync::MaybeArc<
+  node_resolver::PackageJsonResolver<DenoFsNodeResolverEnv>,
+>;
 
 #[derive(Debug)]
 pub struct DenoFsNodeResolverEnv {
diff --git a/ext/node/ops/blocklist.rs b/ext/node/ops/blocklist.rs
index 332cdda8f9..6c64d68eca 100644
--- a/ext/node/ops/blocklist.rs
+++ b/ext/node/ops/blocklist.rs
@@ -7,9 +7,6 @@ use std::net::Ipv4Addr;
 use std::net::Ipv6Addr;
 use std::net::SocketAddr;
 
-use deno_core::anyhow::anyhow;
-use deno_core::anyhow::bail;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 
@@ -27,13 +24,25 @@ impl deno_core::GarbageCollected for BlockListResource {}
 #[derive(Serialize)]
 struct SocketAddressSerialization(String, String);
 
+#[derive(Debug, thiserror::Error)]
+pub enum BlocklistError {
+  #[error("{0}")]
+  AddrParse(#[from] std::net::AddrParseError),
+  #[error("{0}")]
+  IpNetwork(#[from] ipnetwork::IpNetworkError),
+  #[error("Invalid address")]
+  InvalidAddress,
+  #[error("IP version mismatch between start and end addresses")]
+  IpVersionMismatch,
+}
+
 #[op2(fast)]
 pub fn op_socket_address_parse(
   state: &mut OpState,
   #[string] addr: &str,
   #[smi] port: u16,
   #[string] family: &str,
-) -> Result<bool, AnyError> {
+) -> Result<bool, BlocklistError> {
   let ip = addr.parse::<IpAddr>()?;
   let parsed: SocketAddr = SocketAddr::new(ip, port);
   let parsed_ip_str = parsed.ip().to_string();
@@ -52,7 +61,7 @@ pub fn op_socket_address_parse(
       Ok(false)
     }
   } else {
-    Err(anyhow!("Invalid address"))
+    Err(BlocklistError::InvalidAddress)
   }
 }
 
@@ -60,8 +69,8 @@ pub fn op_socket_address_parse(
 #[serde]
 pub fn op_socket_address_get_serialization(
   state: &mut OpState,
-) -> Result<SocketAddressSerialization, AnyError> {
-  Ok(state.take::<SocketAddressSerialization>())
+) -> SocketAddressSerialization {
+  state.take::<SocketAddressSerialization>()
 }
 
 #[op2]
@@ -77,7 +86,7 @@ pub fn op_blocklist_new() -> BlockListResource {
 pub fn op_blocklist_add_address(
   #[cppgc] wrap: &BlockListResource,
   #[string] addr: &str,
-) -> Result<(), AnyError> {
+) -> Result<(), BlocklistError> {
   wrap.blocklist.borrow_mut().add_address(addr)
 }
 
@@ -86,7 +95,7 @@ pub fn op_blocklist_add_range(
   #[cppgc] wrap: &BlockListResource,
   #[string] start: &str,
   #[string] end: &str,
-) -> Result<bool, AnyError> {
+) -> Result<bool, BlocklistError> {
   wrap.blocklist.borrow_mut().add_range(start, end)
 }
 
@@ -95,7 +104,7 @@ pub fn op_blocklist_add_subnet(
   #[cppgc] wrap: &BlockListResource,
   #[string] addr: &str,
   #[smi] prefix: u8,
-) -> Result<(), AnyError> {
+) -> Result<(), BlocklistError> {
   wrap.blocklist.borrow_mut().add_subnet(addr, prefix)
 }
 
@@ -104,7 +113,7 @@ pub fn op_blocklist_check(
   #[cppgc] wrap: &BlockListResource,
   #[string] addr: &str,
   #[string] r#type: &str,
-) -> Result<bool, AnyError> {
+) -> Result<bool, BlocklistError> {
   wrap.blocklist.borrow().check(addr, r#type)
 }
 
@@ -123,7 +132,7 @@ impl BlockList {
     &mut self,
     addr: IpAddr,
     prefix: Option<u8>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), BlocklistError> {
     match addr {
       IpAddr::V4(addr) => {
         let ipv4_prefix = prefix.unwrap_or(32);
@@ -154,7 +163,7 @@ impl BlockList {
     Ok(())
   }
 
-  pub fn add_address(&mut self, address: &str) -> Result<(), AnyError> {
+  pub fn add_address(&mut self, address: &str) -> Result<(), BlocklistError> {
     let ip: IpAddr = address.parse()?;
     self.map_addr_add_network(ip, None)?;
     Ok(())
@@ -164,7 +173,7 @@ impl BlockList {
     &mut self,
     start: &str,
     end: &str,
-  ) -> Result<bool, AnyError> {
+  ) -> Result<bool, BlocklistError> {
     let start_ip: IpAddr = start.parse()?;
     let end_ip: IpAddr = end.parse()?;
 
@@ -193,25 +202,33 @@ impl BlockList {
           self.map_addr_add_network(IpAddr::V6(addr), None)?;
         }
       }
-      _ => bail!("IP version mismatch between start and end addresses"),
+      _ => return Err(BlocklistError::IpVersionMismatch),
     }
     Ok(true)
   }
 
-  pub fn add_subnet(&mut self, addr: &str, prefix: u8) -> Result<(), AnyError> {
+  pub fn add_subnet(
+    &mut self,
+    addr: &str,
+    prefix: u8,
+  ) -> Result<(), BlocklistError> {
     let ip: IpAddr = addr.parse()?;
     self.map_addr_add_network(ip, Some(prefix))?;
     Ok(())
   }
 
-  pub fn check(&self, addr: &str, r#type: &str) -> Result<bool, AnyError> {
+  pub fn check(
+    &self,
+    addr: &str,
+    r#type: &str,
+  ) -> Result<bool, BlocklistError> {
     let addr: IpAddr = addr.parse()?;
     let family = r#type.to_lowercase();
     if family == "ipv4" && addr.is_ipv4() || family == "ipv6" && addr.is_ipv6()
     {
       Ok(self.rules.iter().any(|net| net.contains(addr)))
     } else {
-      Err(anyhow!("Invalid address"))
+      Err(BlocklistError::InvalidAddress)
     }
   }
 }
diff --git a/ext/node/ops/crypto/keys.rs b/ext/node/ops/crypto/keys.rs
index 867b34e044..ac62f5ccae 100644
--- a/ext/node/ops/crypto/keys.rs
+++ b/ext/node/ops/crypto/keys.rs
@@ -2024,7 +2024,9 @@ pub fn op_node_export_public_key_pem(
     _ => unreachable!("export_der would have errored"),
   };
 
-  let mut out = vec![0; 2048];
+  let pem_len = der::pem::encapsulated_len(label, LineEnding::LF, data.len())
+    .map_err(|_| type_error("very large data"))?;
+  let mut out = vec![0; pem_len];
   let mut writer = PemWriter::new(label, LineEnding::LF, &mut out)?;
   writer.write(&data)?;
   let len = writer.finish()?;
@@ -2063,7 +2065,9 @@ pub fn op_node_export_private_key_pem(
     _ => unreachable!("export_der would have errored"),
   };
 
-  let mut out = vec![0; 2048];
+  let pem_len = der::pem::encapsulated_len(label, LineEnding::LF, data.len())
+    .map_err(|_| type_error("very large data"))?;
+  let mut out = vec![0; pem_len];
   let mut writer = PemWriter::new(label, LineEnding::LF, &mut out)?;
   writer.write(&data)?;
   let len = writer.finish()?;
diff --git a/ext/node/ops/crypto/mod.rs b/ext/node/ops/crypto/mod.rs
index 600d315587..0cf34511b4 100644
--- a/ext/node/ops/crypto/mod.rs
+++ b/ext/node/ops/crypto/mod.rs
@@ -519,11 +519,11 @@ pub fn op_node_dh_compute_secret(
 }
 
 #[op2(fast)]
-#[smi]
+#[number]
 pub fn op_node_random_int(
-  #[smi] min: i32,
-  #[smi] max: i32,
-) -> Result<i32, AnyError> {
+  #[number] min: i64,
+  #[number] max: i64,
+) -> Result<i64, AnyError> {
   let mut rng = rand::thread_rng();
   // Uniform distribution is required to avoid Modulo Bias
   // https://en.wikipedia.org/wiki/Fisher–Yates_shuffle#Modulo_bias
diff --git a/ext/node/ops/crypto/sign.rs b/ext/node/ops/crypto/sign.rs
index b7779a5d80..31744f86ba 100644
--- a/ext/node/ops/crypto/sign.rs
+++ b/ext/node/ops/crypto/sign.rs
@@ -79,18 +79,15 @@ impl KeyObjectHandle {
       AsymmetricPrivateKey::RsaPss(key) => {
         let mut hash_algorithm = None;
         let mut salt_length = None;
-        match &key.details {
-          Some(details) => {
-            if details.hash_algorithm != details.mf1_hash_algorithm {
-              return Err(type_error(
+        if let Some(details) = &key.details {
+          if details.hash_algorithm != details.mf1_hash_algorithm {
+            return Err(type_error(
                 "rsa-pss with different mf1 hash algorithm and hash algorithm is not supported",
               ));
-            }
-            hash_algorithm = Some(details.hash_algorithm);
-            salt_length = Some(details.salt_length as usize);
           }
-          None => {}
-        };
+          hash_algorithm = Some(details.hash_algorithm);
+          salt_length = Some(details.salt_length as usize);
+        }
         if let Some(s) = pss_salt_length {
           salt_length = Some(s as usize);
         }
@@ -215,18 +212,15 @@ impl KeyObjectHandle {
       AsymmetricPublicKey::RsaPss(key) => {
         let mut hash_algorithm = None;
         let mut salt_length = None;
-        match &key.details {
-          Some(details) => {
-            if details.hash_algorithm != details.mf1_hash_algorithm {
-              return Err(type_error(
+        if let Some(details) = &key.details {
+          if details.hash_algorithm != details.mf1_hash_algorithm {
+            return Err(type_error(
                 "rsa-pss with different mf1 hash algorithm and hash algorithm is not supported",
               ));
-            }
-            hash_algorithm = Some(details.hash_algorithm);
-            salt_length = Some(details.salt_length as usize);
           }
-          None => {}
-        };
+          hash_algorithm = Some(details.hash_algorithm);
+          salt_length = Some(details.salt_length as usize);
+        }
         if let Some(s) = pss_salt_length {
           salt_length = Some(s as usize);
         }
diff --git a/ext/node/ops/fs.rs b/ext/node/ops/fs.rs
index 6253f32d05..98b3c46a14 100644
--- a/ext/node/ops/fs.rs
+++ b/ext/node/ops/fs.rs
@@ -3,7 +3,6 @@
 use std::cell::RefCell;
 use std::rc::Rc;
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_fs::FileSystemRc;
@@ -11,11 +10,27 @@ use serde::Serialize;
 
 use crate::NodePermissions;
 
+#[derive(Debug, thiserror::Error)]
+pub enum FsError {
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[cfg(windows)]
+  #[error("Path has no root.")]
+  PathHasNoRoot,
+  #[cfg(not(any(unix, windows)))]
+  #[error("Unsupported platform.")]
+  UnsupportedPlatform,
+  #[error(transparent)]
+  Fs(#[from] deno_io::fs::FsError),
+}
+
 #[op2(fast)]
 pub fn op_node_fs_exists_sync<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<bool, AnyError>
+) -> Result<bool, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
@@ -30,7 +45,7 @@ where
 pub async fn op_node_fs_exists<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
-) -> Result<bool, AnyError>
+) -> Result<bool, FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -38,7 +53,8 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_read_with_api_name(&path, Some("node:fs.exists()"))?;
+      .check_read_with_api_name(&path, Some("node:fs.exists()"))
+      .map_err(FsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -50,16 +66,18 @@ pub fn op_node_cp_sync<P>(
   state: &mut OpState,
   #[string] path: &str,
   #[string] new_path: &str,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_read_with_api_name(path, Some("node:fs.cpSync"))?;
+    .check_read_with_api_name(path, Some("node:fs.cpSync"))
+    .map_err(FsError::Permission)?;
   let new_path = state
     .borrow_mut::<P>()
-    .check_write_with_api_name(new_path, Some("node:fs.cpSync"))?;
+    .check_write_with_api_name(new_path, Some("node:fs.cpSync"))
+    .map_err(FsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.cp_sync(&path, &new_path)?;
@@ -71,7 +89,7 @@ pub async fn op_node_cp<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   #[string] new_path: String,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -79,10 +97,12 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_read_with_api_name(&path, Some("node:fs.cpSync"))?;
+      .check_read_with_api_name(&path, Some("node:fs.cpSync"))
+      .map_err(FsError::Permission)?;
     let new_path = state
       .borrow_mut::<P>()
-      .check_write_with_api_name(&new_path, Some("node:fs.cpSync"))?;
+      .check_write_with_api_name(&new_path, Some("node:fs.cpSync"))
+      .map_err(FsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path, new_path)
   };
 
@@ -108,7 +128,7 @@ pub fn op_node_statfs<P>(
   state: Rc<RefCell<OpState>>,
   #[string] path: String,
   bigint: bool,
-) -> Result<StatFs, AnyError>
+) -> Result<StatFs, FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -116,10 +136,12 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_read_with_api_name(&path, Some("node:fs.statfs"))?;
+      .check_read_with_api_name(&path, Some("node:fs.statfs"))
+      .map_err(FsError::Permission)?;
     state
       .borrow_mut::<P>()
-      .check_sys("statfs", "node:fs.statfs")?;
+      .check_sys("statfs", "node:fs.statfs")
+      .map_err(FsError::Permission)?;
     path
   };
   #[cfg(unix)]
@@ -130,13 +152,21 @@ where
     let mut cpath = path.as_bytes().to_vec();
     cpath.push(0);
     if bigint {
-      #[cfg(not(target_os = "macos"))]
+      #[cfg(not(any(
+        target_os = "macos",
+        target_os = "freebsd",
+        target_os = "openbsd"
+      )))]
       // SAFETY: `cpath` is NUL-terminated and result is pointer to valid statfs memory.
       let (code, result) = unsafe {
         let mut result: libc::statfs64 = std::mem::zeroed();
         (libc::statfs64(cpath.as_ptr() as _, &mut result), result)
       };
-      #[cfg(target_os = "macos")]
+      #[cfg(any(
+        target_os = "macos",
+        target_os = "freebsd",
+        target_os = "openbsd"
+      ))]
       // SAFETY: `cpath` is NUL-terminated and result is pointer to valid statfs memory.
       let (code, result) = unsafe {
         let mut result: libc::statfs = std::mem::zeroed();
@@ -146,7 +176,10 @@ where
         return Err(std::io::Error::last_os_error().into());
       }
       Ok(StatFs {
+        #[cfg(not(target_os = "openbsd"))]
         typ: result.f_type as _,
+        #[cfg(target_os = "openbsd")]
+        typ: 0 as _,
         bsize: result.f_bsize as _,
         blocks: result.f_blocks as _,
         bfree: result.f_bfree as _,
@@ -164,7 +197,10 @@ where
         return Err(std::io::Error::last_os_error().into());
       }
       Ok(StatFs {
+        #[cfg(not(target_os = "openbsd"))]
         typ: result.f_type as _,
+        #[cfg(target_os = "openbsd")]
+        typ: 0 as _,
         bsize: result.f_bsize as _,
         blocks: result.f_blocks as _,
         bfree: result.f_bfree as _,
@@ -176,7 +212,6 @@ where
   }
   #[cfg(windows)]
   {
-    use deno_core::anyhow::anyhow;
     use std::ffi::OsStr;
     use std::os::windows::ffi::OsStrExt;
     use windows_sys::Win32::Storage::FileSystem::GetDiskFreeSpaceW;
@@ -186,10 +221,7 @@ where
     // call below.
     #[allow(clippy::disallowed_methods)]
     let path = path.canonicalize()?;
-    let root = path
-      .ancestors()
-      .last()
-      .ok_or(anyhow!("Path has no root."))?;
+    let root = path.ancestors().last().ok_or(FsError::PathHasNoRoot)?;
     let mut root = OsStr::new(root).encode_wide().collect::<Vec<_>>();
     root.push(0);
     let mut sectors_per_cluster = 0;
@@ -229,7 +261,7 @@ where
   {
     let _ = path;
     let _ = bigint;
-    Err(anyhow!("Unsupported platform."))
+    Err(FsError::UnsupportedPlatform)
   }
 }
 
@@ -241,13 +273,14 @@ pub fn op_node_lutimes_sync<P>(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write_with_api_name(path, Some("node:fs.lutimes"))?;
+    .check_write_with_api_name(path, Some("node:fs.lutimes"))
+    .map_err(FsError::Permission)?;
 
   let fs = state.borrow::<FileSystemRc>();
   fs.lutime_sync(&path, atime_secs, atime_nanos, mtime_secs, mtime_nanos)?;
@@ -262,7 +295,7 @@ pub async fn op_node_lutimes<P>(
   #[smi] atime_nanos: u32,
   #[number] mtime_secs: i64,
   #[smi] mtime_nanos: u32,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -270,7 +303,8 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_write_with_api_name(&path, Some("node:fs.lutimesSync"))?;
+      .check_write_with_api_name(&path, Some("node:fs.lutimesSync"))
+      .map_err(FsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
 
@@ -286,13 +320,14 @@ pub fn op_node_lchown_sync<P>(
   #[string] path: String,
   uid: Option<u32>,
   gid: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
   let path = state
     .borrow_mut::<P>()
-    .check_write_with_api_name(&path, Some("node:fs.lchownSync"))?;
+    .check_write_with_api_name(&path, Some("node:fs.lchownSync"))
+    .map_err(FsError::Permission)?;
   let fs = state.borrow::<FileSystemRc>();
   fs.lchown_sync(&path, uid, gid)?;
   Ok(())
@@ -304,7 +339,7 @@ pub async fn op_node_lchown<P>(
   #[string] path: String,
   uid: Option<u32>,
   gid: Option<u32>,
-) -> Result<(), AnyError>
+) -> Result<(), FsError>
 where
   P: NodePermissions + 'static,
 {
@@ -312,7 +347,8 @@ where
     let mut state = state.borrow_mut();
     let path = state
       .borrow_mut::<P>()
-      .check_write_with_api_name(&path, Some("node:fs.lchown"))?;
+      .check_write_with_api_name(&path, Some("node:fs.lchown"))
+      .map_err(FsError::Permission)?;
     (state.borrow::<FileSystemRc>().clone(), path)
   };
   fs.lchown_async(path, uid, gid).await?;
diff --git a/ext/node/ops/http.rs b/ext/node/ops/http.rs
index 773902dedf..730e1e482b 100644
--- a/ext/node/ops/http.rs
+++ b/ext/node/ops/http.rs
@@ -8,14 +8,12 @@ use std::task::Context;
 use std::task::Poll;
 
 use bytes::Bytes;
-use deno_core::anyhow;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::stream::Peekable;
 use deno_core::futures::Future;
 use deno_core::futures::FutureExt;
 use deno_core::futures::Stream;
 use deno_core::futures::StreamExt;
+use deno_core::futures::TryFutureExt;
 use deno_core::op2;
 use deno_core::serde::Serialize;
 use deno_core::unsync::spawn;
@@ -33,6 +31,7 @@ use deno_core::Resource;
 use deno_core::ResourceId;
 use deno_fetch::get_or_create_client_from_state;
 use deno_fetch::FetchCancelHandle;
+use deno_fetch::FetchError;
 use deno_fetch::FetchRequestResource;
 use deno_fetch::FetchReturn;
 use deno_fetch::HttpClientResource;
@@ -59,12 +58,15 @@ pub fn op_node_http_request<P>(
   #[serde] headers: Vec<(ByteString, ByteString)>,
   #[smi] client_rid: Option<u32>,
   #[smi] body: Option<ResourceId>,
-) -> Result<FetchReturn, AnyError>
+) -> Result<FetchReturn, FetchError>
 where
   P: crate::NodePermissions + 'static,
 {
   let client = if let Some(rid) = client_rid {
-    let r = state.resource_table.get::<HttpClientResource>(rid)?;
+    let r = state
+      .resource_table
+      .get::<HttpClientResource>(rid)
+      .map_err(FetchError::Resource)?;
     r.client.clone()
   } else {
     get_or_create_client_from_state(state)?
@@ -76,15 +78,15 @@ where
 
   {
     let permissions = state.borrow_mut::<P>();
-    permissions.check_net_url(&url, "ClientRequest")?;
+    permissions
+      .check_net_url(&url, "ClientRequest")
+      .map_err(FetchError::Permission)?;
   }
 
   let mut header_map = HeaderMap::new();
   for (key, value) in headers {
-    let name = HeaderName::from_bytes(&key)
-      .map_err(|err| type_error(err.to_string()))?;
-    let v = HeaderValue::from_bytes(&value)
-      .map_err(|err| type_error(err.to_string()))?;
+    let name = HeaderName::from_bytes(&key)?;
+    let v = HeaderValue::from_bytes(&value)?;
 
     header_map.append(name, v);
   }
@@ -92,7 +94,10 @@ where
   let (body, con_len) = if let Some(body) = body {
     (
       BodyExt::boxed(NodeHttpResourceToBodyAdapter::new(
-        state.resource_table.take_any(body)?,
+        state
+          .resource_table
+          .take_any(body)
+          .map_err(FetchError::Resource)?,
       )),
       None,
     )
@@ -117,7 +122,7 @@ where
   *request.uri_mut() = url
     .as_str()
     .parse()
-    .map_err(|_| type_error("Invalid URL"))?;
+    .map_err(|_| FetchError::InvalidUrl(url.clone()))?;
   *request.headers_mut() = header_map;
 
   if let Some((username, password)) = maybe_authority {
@@ -136,9 +141,9 @@ where
   let fut = async move {
     client
       .send(request)
+      .map_err(Into::into)
       .or_cancel(cancel_handle_)
       .await
-      .map(|res| res.map_err(|err| type_error(err.to_string())))
   };
 
   let request_rid = state.resource_table.add(FetchRequestResource {
@@ -174,11 +179,12 @@ pub struct NodeHttpFetchResponse {
 pub async fn op_node_http_fetch_send(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<NodeHttpFetchResponse, AnyError> {
+) -> Result<NodeHttpFetchResponse, FetchError> {
   let request = state
     .borrow_mut()
     .resource_table
-    .take::<FetchRequestResource>(rid)?;
+    .take::<FetchRequestResource>(rid)
+    .map_err(FetchError::Resource)?;
 
   let request = Rc::try_unwrap(request)
     .ok()
@@ -191,22 +197,23 @@ pub async fn op_node_http_fetch_send(
       // If any error in the chain is a hyper body error, return that as a special result we can use to
       // reconstruct an error chain (eg: `new TypeError(..., { cause: new Error(...) })`).
       // TODO(mmastrac): it would be a lot easier if we just passed a v8::Global through here instead
-      let mut err_ref: &dyn std::error::Error = err.as_ref();
-      while let Some(err) = std::error::Error::source(err_ref) {
-        if let Some(err) = err.downcast_ref::<hyper::Error>() {
-          if let Some(err) = std::error::Error::source(err) {
-            return Ok(NodeHttpFetchResponse {
-              error: Some(err.to_string()),
-              ..Default::default()
-            });
+
+      if let FetchError::ClientSend(err_src) = &err {
+        if let Some(client_err) = std::error::Error::source(&err_src.source) {
+          if let Some(err_src) = client_err.downcast_ref::<hyper::Error>() {
+            if let Some(err_src) = std::error::Error::source(err_src) {
+              return Ok(NodeHttpFetchResponse {
+                error: Some(err_src.to_string()),
+                ..Default::default()
+              });
+            }
           }
         }
-        err_ref = err;
       }
 
-      return Err(type_error(err.to_string()));
+      return Err(err);
     }
-    Err(_) => return Err(type_error("request was cancelled")),
+    Err(_) => return Err(FetchError::RequestCanceled),
   };
 
   let status = res.status();
@@ -250,11 +257,12 @@ pub async fn op_node_http_fetch_send(
 pub async fn op_node_http_fetch_response_upgrade(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, FetchError> {
   let raw_response = state
     .borrow_mut()
     .resource_table
-    .take::<NodeHttpFetchResponseResource>(rid)?;
+    .take::<NodeHttpFetchResponseResource>(rid)
+    .map_err(FetchError::Resource)?;
   let raw_response = Rc::try_unwrap(raw_response)
     .expect("Someone is holding onto NodeHttpFetchResponseResource");
 
@@ -277,7 +285,7 @@ pub async fn op_node_http_fetch_response_upgrade(
         }
         read_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, FetchError>(())
     });
     spawn(async move {
       let mut buf = [0; 1024];
@@ -288,7 +296,7 @@ pub async fn op_node_http_fetch_response_upgrade(
         }
         upgraded_tx.write_all(&buf[..read]).await?;
       }
-      Ok::<_, AnyError>(())
+      Ok::<_, FetchError>(())
     });
   }
 
@@ -318,23 +326,26 @@ impl UpgradeStream {
     }
   }
 
-  async fn read(self: Rc<Self>, buf: &mut [u8]) -> Result<usize, AnyError> {
+  async fn read(
+    self: Rc<Self>,
+    buf: &mut [u8],
+  ) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let read = RcRef::map(self, |this| &this.read);
       let mut read = read.borrow_mut().await;
-      Ok(Pin::new(&mut *read).read(buf).await?)
+      Pin::new(&mut *read).read(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
   }
 
-  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, AnyError> {
+  async fn write(self: Rc<Self>, buf: &[u8]) -> Result<usize, std::io::Error> {
     let cancel_handle = RcRef::map(self.clone(), |this| &this.cancel_handle);
     async {
       let write = RcRef::map(self, |this| &this.write);
       let mut write = write.borrow_mut().await;
-      Ok(Pin::new(&mut *write).write(buf).await?)
+      Pin::new(&mut *write).write(buf).await
     }
     .try_or_cancel(cancel_handle)
     .await
@@ -387,7 +398,7 @@ impl NodeHttpFetchResponseResource {
     }
   }
 
-  pub async fn upgrade(self) -> Result<hyper::upgrade::Upgraded, AnyError> {
+  pub async fn upgrade(self) -> Result<hyper::upgrade::Upgraded, hyper::Error> {
     let reader = self.response_reader.into_inner();
     match reader {
       NodeHttpFetchResponseReader::Start(resp) => {
@@ -445,7 +456,9 @@ impl Resource for NodeHttpFetchResponseResource {
             // safely call `await` on it without creating a race condition.
             Some(_) => match reader.as_mut().next().await.unwrap() {
               Ok(chunk) => assert!(chunk.is_empty()),
-              Err(err) => break Err(type_error(err.to_string())),
+              Err(err) => {
+                break Err(deno_core::error::type_error(err.to_string()))
+              }
             },
             None => break Ok(BufView::empty()),
           }
@@ -453,7 +466,7 @@ impl Resource for NodeHttpFetchResponseResource {
       };
 
       let cancel_handle = RcRef::map(self, |r| &r.cancel);
-      fut.try_or_cancel(cancel_handle).await
+      fut.try_or_cancel(cancel_handle).await.map_err(Into::into)
     })
   }
 
@@ -469,7 +482,9 @@ impl Resource for NodeHttpFetchResponseResource {
 #[allow(clippy::type_complexity)]
 pub struct NodeHttpResourceToBodyAdapter(
   Rc<dyn Resource>,
-  Option<Pin<Box<dyn Future<Output = Result<BufView, anyhow::Error>>>>>,
+  Option<
+    Pin<Box<dyn Future<Output = Result<BufView, deno_core::anyhow::Error>>>>,
+  >,
 );
 
 impl NodeHttpResourceToBodyAdapter {
@@ -485,7 +500,7 @@ unsafe impl Send for NodeHttpResourceToBodyAdapter {}
 unsafe impl Sync for NodeHttpResourceToBodyAdapter {}
 
 impl Stream for NodeHttpResourceToBodyAdapter {
-  type Item = Result<Bytes, anyhow::Error>;
+  type Item = Result<Bytes, deno_core::anyhow::Error>;
 
   fn poll_next(
     self: Pin<&mut Self>,
@@ -515,7 +530,7 @@ impl Stream for NodeHttpResourceToBodyAdapter {
 
 impl hyper::body::Body for NodeHttpResourceToBodyAdapter {
   type Data = Bytes;
-  type Error = anyhow::Error;
+  type Error = deno_core::anyhow::Error;
 
   fn poll_frame(
     self: Pin<&mut Self>,
diff --git a/ext/node/ops/http2.rs b/ext/node/ops/http2.rs
index 9595cb33d6..53dada9f41 100644
--- a/ext/node/ops/http2.rs
+++ b/ext/node/ops/http2.rs
@@ -7,7 +7,6 @@ use std::rc::Rc;
 use std::task::Poll;
 
 use bytes::Bytes;
-use deno_core::error::AnyError;
 use deno_core::futures::future::poll_fn;
 use deno_core::op2;
 use deno_core::serde::Serialize;
@@ -110,17 +109,28 @@ impl Resource for Http2ServerSendResponse {
   }
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum Http2Error {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  UrlParse(#[from] url::ParseError),
+  #[error(transparent)]
+  H2(#[from] h2::Error),
+}
+
 #[op2(async)]
 #[serde]
 pub async fn op_http2_connect(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[string] url: String,
-) -> Result<(ResourceId, ResourceId), AnyError> {
+) -> Result<(ResourceId, ResourceId), Http2Error> {
   // No permission check necessary because we're using an existing connection
   let network_stream = {
     let mut state = state.borrow_mut();
-    take_network_stream_resource(&mut state.resource_table, rid)?
+    take_network_stream_resource(&mut state.resource_table, rid)
+      .map_err(Http2Error::Resource)?
   };
 
   let url = Url::parse(&url)?;
@@ -144,9 +154,10 @@ pub async fn op_http2_connect(
 pub async fn op_http2_listen(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, Http2Error> {
   let stream =
-    take_network_stream_resource(&mut state.borrow_mut().resource_table, rid)?;
+    take_network_stream_resource(&mut state.borrow_mut().resource_table, rid)
+      .map_err(Http2Error::Resource)?;
 
   let conn = h2::server::Builder::new().handshake(stream).await?;
   Ok(
@@ -166,12 +177,13 @@ pub async fn op_http2_accept(
   #[smi] rid: ResourceId,
 ) -> Result<
   Option<(Vec<(ByteString, ByteString)>, ResourceId, ResourceId)>,
-  AnyError,
+  Http2Error,
 > {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ServerConnection>(rid)?;
+    .get::<Http2ServerConnection>(rid)
+    .map_err(Http2Error::Resource)?;
   let mut conn = RcRef::map(&resource, |r| &r.conn).borrow_mut().await;
   if let Some(res) = conn.accept().await {
     let (req, resp) = res?;
@@ -233,11 +245,12 @@ pub async fn op_http2_send_response(
   #[smi] rid: ResourceId,
   #[smi] status: u16,
   #[serde] headers: Vec<(ByteString, ByteString)>,
-) -> Result<(ResourceId, u32), AnyError> {
+) -> Result<(ResourceId, u32), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ServerSendResponse>(rid)?;
+    .get::<Http2ServerSendResponse>(rid)
+    .map_err(Http2Error::Resource)?;
   let mut send_response = RcRef::map(resource, |r| &r.send_response)
     .borrow_mut()
     .await;
@@ -262,8 +275,12 @@ pub async fn op_http2_send_response(
 pub async fn op_http2_poll_client_connection(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
-  let resource = state.borrow().resource_table.get::<Http2ClientConn>(rid)?;
+) -> Result<(), Http2Error> {
+  let resource = state
+    .borrow()
+    .resource_table
+    .get::<Http2ClientConn>(rid)
+    .map_err(Http2Error::Resource)?;
 
   let cancel_handle = RcRef::map(resource.clone(), |this| &this.cancel_handle);
   let mut conn = RcRef::map(resource, |this| &this.conn).borrow_mut().await;
@@ -289,11 +306,12 @@ pub async fn op_http2_client_request(
   // 4 strings of keys?
   #[serde] mut pseudo_headers: HashMap<String, String>,
   #[serde] headers: Vec<(ByteString, ByteString)>,
-) -> Result<(ResourceId, u32), AnyError> {
+) -> Result<(ResourceId, u32), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2Client>(client_rid)?;
+    .get::<Http2Client>(client_rid)
+    .map_err(Http2Error::Resource)?;
 
   let url = resource.url.clone();
 
@@ -326,7 +344,10 @@ pub async fn op_http2_client_request(
 
   let resource = {
     let state = state.borrow();
-    state.resource_table.get::<Http2Client>(client_rid)?
+    state
+      .resource_table
+      .get::<Http2Client>(client_rid)
+      .map_err(Http2Error::Resource)?
   };
   let mut client = RcRef::map(&resource, |r| &r.client).borrow_mut().await;
   poll_fn(|cx| client.poll_ready(cx)).await?;
@@ -345,11 +366,12 @@ pub async fn op_http2_client_send_data(
   #[smi] stream_rid: ResourceId,
   #[buffer] data: JsBuffer,
   end_of_stream: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ClientStream>(stream_rid)?;
+    .get::<Http2ClientStream>(stream_rid)
+    .map_err(Http2Error::Resource)?;
   let mut stream = RcRef::map(&resource, |r| &r.stream).borrow_mut().await;
 
   stream.send_data(data.to_vec().into(), end_of_stream)?;
@@ -361,7 +383,7 @@ pub async fn op_http2_client_reset_stream(
   state: Rc<RefCell<OpState>>,
   #[smi] stream_rid: ResourceId,
   #[smi] code: u32,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let resource = state
     .borrow()
     .resource_table
@@ -376,11 +398,12 @@ pub async fn op_http2_client_send_trailers(
   state: Rc<RefCell<OpState>>,
   #[smi] stream_rid: ResourceId,
   #[serde] trailers: Vec<(ByteString, ByteString)>,
-) -> Result<(), AnyError> {
+) -> Result<(), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ClientStream>(stream_rid)?;
+    .get::<Http2ClientStream>(stream_rid)
+    .map_err(Http2Error::Resource)?;
   let mut stream = RcRef::map(&resource, |r| &r.stream).borrow_mut().await;
 
   let mut trailers_map = http::HeaderMap::new();
@@ -408,11 +431,12 @@ pub struct Http2ClientResponse {
 pub async fn op_http2_client_get_response(
   state: Rc<RefCell<OpState>>,
   #[smi] stream_rid: ResourceId,
-) -> Result<(Http2ClientResponse, bool), AnyError> {
+) -> Result<(Http2ClientResponse, bool), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ClientStream>(stream_rid)?;
+    .get::<Http2ClientStream>(stream_rid)
+    .map_err(Http2Error::Resource)?;
   let mut response_future =
     RcRef::map(&resource, |r| &r.response).borrow_mut().await;
 
@@ -478,23 +502,22 @@ fn poll_data_or_trailers(
 pub async fn op_http2_client_get_response_body_chunk(
   state: Rc<RefCell<OpState>>,
   #[smi] body_rid: ResourceId,
-) -> Result<(Option<Vec<u8>>, bool, bool), AnyError> {
+) -> Result<(Option<Vec<u8>>, bool, bool), Http2Error> {
   let resource = state
     .borrow()
     .resource_table
-    .get::<Http2ClientResponseBody>(body_rid)?;
+    .get::<Http2ClientResponseBody>(body_rid)
+    .map_err(Http2Error::Resource)?;
   let mut body = RcRef::map(&resource, |r| &r.body).borrow_mut().await;
 
   loop {
     let result = poll_fn(|cx| poll_data_or_trailers(cx, &mut body)).await;
     if let Err(err) = result {
-      let reason = err.reason();
-      if let Some(reason) = reason {
-        if reason == Reason::CANCEL {
-          return Ok((None, false, true));
-        }
+      match err.reason() {
+        Some(Reason::NO_ERROR) => return Ok((None, true, false)),
+        Some(Reason::CANCEL) => return Ok((None, false, true)),
+        _ => return Err(err.into()),
       }
-      return Err(err.into());
     }
     match result.unwrap() {
       DataOrTrailers::Data(data) => {
@@ -527,7 +550,7 @@ pub async fn op_http2_client_get_response_body_chunk(
 pub async fn op_http2_client_get_response_trailers(
   state: Rc<RefCell<OpState>>,
   #[smi] body_rid: ResourceId,
-) -> Result<Option<Vec<(ByteString, ByteString)>>, AnyError> {
+) -> Result<Option<Vec<(ByteString, ByteString)>>, deno_core::error::AnyError> {
   let resource = state
     .borrow()
     .resource_table
diff --git a/ext/node/ops/idna.rs b/ext/node/ops/idna.rs
index 9c9450c70f..a3d85e77c2 100644
--- a/ext/node/ops/idna.rs
+++ b/ext/node/ops/idna.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::anyhow::Error;
-use deno_core::error::range_error;
 use deno_core::op2;
 
 use std::borrow::Cow;
@@ -11,19 +9,21 @@ use std::borrow::Cow;
 
 const PUNY_PREFIX: &str = "xn--";
 
-fn invalid_input_err() -> Error {
-  range_error("Invalid input")
-}
-
-fn not_basic_err() -> Error {
-  range_error("Illegal input >= 0x80 (not a basic code point)")
+#[derive(Debug, thiserror::Error)]
+pub enum IdnaError {
+  #[error("Invalid input")]
+  InvalidInput,
+  #[error("Input would take more than 63 characters to encode")]
+  InputTooLong,
+  #[error("Illegal input >= 0x80 (not a basic code point)")]
+  IllegalInput,
 }
 
 /// map a domain by mapping each label with the given function
-fn map_domain<E>(
+fn map_domain(
   domain: &str,
-  f: impl Fn(&str) -> Result<Cow<'_, str>, E>,
-) -> Result<String, E> {
+  f: impl Fn(&str) -> Result<Cow<'_, str>, IdnaError>,
+) -> Result<String, IdnaError> {
   let mut result = String::with_capacity(domain.len());
   let mut domain = domain;
 
@@ -48,7 +48,7 @@ fn map_domain<E>(
 /// Maps a unicode domain to ascii by punycode encoding each label
 ///
 /// Note this is not IDNA2003 or IDNA2008 compliant, rather it matches node.js's punycode implementation
-fn to_ascii(input: &str) -> Result<String, Error> {
+fn to_ascii(input: &str) -> Result<String, IdnaError> {
   if input.is_ascii() {
     return Ok(input.into());
   }
@@ -61,9 +61,7 @@ fn to_ascii(input: &str) -> Result<String, Error> {
     } else {
       idna::punycode::encode_str(label)
         .map(|encoded| [PUNY_PREFIX, &encoded].join("").into()) // add the prefix
-        .ok_or_else(|| {
-          Error::msg("Input would take more than 63 characters to encode") // only error possible per the docs
-        })
+        .ok_or(IdnaError::InputTooLong) // only error possible per the docs
     }
   })?;
 
@@ -74,13 +72,13 @@ fn to_ascii(input: &str) -> Result<String, Error> {
 /// Maps an ascii domain to unicode by punycode decoding each label
 ///
 /// Note this is not IDNA2003 or IDNA2008 compliant, rather it matches node.js's punycode implementation
-fn to_unicode(input: &str) -> Result<String, Error> {
+fn to_unicode(input: &str) -> Result<String, IdnaError> {
   map_domain(input, |s| {
     if let Some(puny) = s.strip_prefix(PUNY_PREFIX) {
       // it's a punycode encoded label
       Ok(
         idna::punycode::decode_to_string(&puny.to_lowercase())
-          .ok_or_else(invalid_input_err)?
+          .ok_or(IdnaError::InvalidInput)?
           .into(),
       )
     } else {
@@ -95,7 +93,7 @@ fn to_unicode(input: &str) -> Result<String, Error> {
 #[string]
 pub fn op_node_idna_punycode_to_ascii(
   #[string] domain: String,
-) -> Result<String, Error> {
+) -> Result<String, IdnaError> {
   to_ascii(&domain)
 }
 
@@ -105,7 +103,7 @@ pub fn op_node_idna_punycode_to_ascii(
 #[string]
 pub fn op_node_idna_punycode_to_unicode(
   #[string] domain: String,
-) -> Result<String, Error> {
+) -> Result<String, IdnaError> {
   to_unicode(&domain)
 }
 
@@ -115,8 +113,8 @@ pub fn op_node_idna_punycode_to_unicode(
 #[string]
 pub fn op_node_idna_domain_to_ascii(
   #[string] domain: String,
-) -> Result<String, Error> {
-  idna::domain_to_ascii(&domain).map_err(|e| e.into())
+) -> Result<String, idna::Errors> {
+  idna::domain_to_ascii(&domain)
 }
 
 /// Converts a domain to Unicode as per the IDNA spec
@@ -131,7 +129,7 @@ pub fn op_node_idna_domain_to_unicode(#[string] domain: String) -> String {
 #[string]
 pub fn op_node_idna_punycode_decode(
   #[string] domain: String,
-) -> Result<String, Error> {
+) -> Result<String, IdnaError> {
   if domain.is_empty() {
     return Ok(domain);
   }
@@ -147,11 +145,10 @@ pub fn op_node_idna_punycode_decode(
       .unwrap_or(domain.len() - 1);
 
   if !domain[..last_dash].is_ascii() {
-    return Err(not_basic_err());
+    return Err(IdnaError::IllegalInput);
   }
 
-  idna::punycode::decode_to_string(&domain)
-    .ok_or_else(|| deno_core::error::range_error("Invalid input"))
+  idna::punycode::decode_to_string(&domain).ok_or(IdnaError::InvalidInput)
 }
 
 #[op2]
diff --git a/ext/node/ops/ipc.rs b/ext/node/ops/ipc.rs
index 59b6fece14..672cf0d707 100644
--- a/ext/node/ops/ipc.rs
+++ b/ext/node/ops/ipc.rs
@@ -17,8 +17,6 @@ mod impl_ {
   use std::task::Context;
   use std::task::Poll;
 
-  use deno_core::error::bad_resource_id;
-  use deno_core::error::AnyError;
   use deno_core::op2;
   use deno_core::serde;
   use deno_core::serde::Serializer;
@@ -167,7 +165,7 @@ mod impl_ {
   #[smi]
   pub fn op_node_child_ipc_pipe(
     state: &mut OpState,
-  ) -> Result<Option<ResourceId>, AnyError> {
+  ) -> Result<Option<ResourceId>, io::Error> {
     let fd = match state.try_borrow_mut::<crate::ChildPipeFd>() {
       Some(child_pipe_fd) => child_pipe_fd.0,
       None => return Ok(None),
@@ -180,6 +178,18 @@ mod impl_ {
     ))
   }
 
+  #[derive(Debug, thiserror::Error)]
+  pub enum IpcError {
+    #[error(transparent)]
+    Resource(deno_core::error::AnyError),
+    #[error(transparent)]
+    IpcJsonStream(#[from] IpcJsonStreamError),
+    #[error(transparent)]
+    Canceled(#[from] deno_core::Canceled),
+    #[error("failed to serialize json value: {0}")]
+    SerdeJson(serde_json::Error),
+  }
+
   #[op2(async)]
   pub fn op_node_ipc_write<'a>(
     scope: &mut v8::HandleScope<'a>,
@@ -192,34 +202,37 @@ mod impl_ {
     // ideally we would just return `Result<(impl Future, bool), ..>`, but that's not
     // supported by `op2` currently.
     queue_ok: v8::Local<'a, v8::Array>,
-  ) -> Result<impl Future<Output = Result<(), AnyError>>, AnyError> {
+  ) -> Result<impl Future<Output = Result<(), io::Error>>, IpcError> {
     let mut serialized = Vec::with_capacity(64);
     let mut ser = serde_json::Serializer::new(&mut serialized);
-    serialize_v8_value(scope, value, &mut ser).map_err(|e| {
-      deno_core::error::type_error(format!(
-        "failed to serialize json value: {e}"
-      ))
-    })?;
+    serialize_v8_value(scope, value, &mut ser).map_err(IpcError::SerdeJson)?;
     serialized.push(b'\n');
 
     let stream = state
       .borrow()
       .resource_table
       .get::<IpcJsonStreamResource>(rid)
-      .map_err(|_| bad_resource_id())?;
+      .map_err(IpcError::Resource)?;
     let old = stream
       .queued_bytes
       .fetch_add(serialized.len(), std::sync::atomic::Ordering::Relaxed);
     if old + serialized.len() > 2 * INITIAL_CAPACITY {
       // sending messages too fast
-      let v = false.to_v8(scope)?;
+      let v = false.to_v8(scope).unwrap(); // Infallible
       queue_ok.set_index(scope, 0, v);
     }
     Ok(async move {
-      stream.clone().write_msg_bytes(&serialized).await?;
+      let cancel = stream.cancel.clone();
+      let result = stream
+        .clone()
+        .write_msg_bytes(&serialized)
+        .or_cancel(cancel)
+        .await;
+      // adjust count even on error
       stream
         .queued_bytes
         .fetch_sub(serialized.len(), std::sync::atomic::Ordering::Relaxed);
+      result??;
       Ok(())
     })
   }
@@ -239,12 +252,12 @@ mod impl_ {
   pub async fn op_node_ipc_read(
     state: Rc<RefCell<OpState>>,
     #[smi] rid: ResourceId,
-  ) -> Result<serde_json::Value, AnyError> {
+  ) -> Result<serde_json::Value, IpcError> {
     let stream = state
       .borrow()
       .resource_table
       .get::<IpcJsonStreamResource>(rid)
-      .map_err(|_| bad_resource_id())?;
+      .map_err(IpcError::Resource)?;
 
     let cancel = stream.cancel.clone();
     let mut stream = RcRef::map(stream, |r| &r.read_half).borrow_mut().await;
@@ -400,7 +413,7 @@ mod impl_ {
     async fn write_msg_bytes(
       self: Rc<Self>,
       msg: &[u8],
-    ) -> Result<(), AnyError> {
+    ) -> Result<(), io::Error> {
       let mut write_half =
         RcRef::map(self, |r| &r.write_half).borrow_mut().await;
       write_half.write_all(msg).await?;
@@ -455,6 +468,14 @@ mod impl_ {
     }
   }
 
+  #[derive(Debug, thiserror::Error)]
+  pub enum IpcJsonStreamError {
+    #[error("{0}")]
+    Io(#[source] std::io::Error),
+    #[error("{0}")]
+    SimdJson(#[source] simd_json::Error),
+  }
+
   // JSON serialization stream over IPC pipe.
   //
   // `\n` is used as a delimiter between messages.
@@ -475,7 +496,7 @@ mod impl_ {
 
     async fn read_msg(
       &mut self,
-    ) -> Result<Option<serde_json::Value>, AnyError> {
+    ) -> Result<Option<serde_json::Value>, IpcJsonStreamError> {
       let mut json = None;
       let nread = read_msg_inner(
         &mut self.pipe,
@@ -483,7 +504,8 @@ mod impl_ {
         &mut json,
         &mut self.read_buffer,
       )
-      .await?;
+      .await
+      .map_err(IpcJsonStreamError::Io)?;
       if nread == 0 {
         // EOF.
         return Ok(None);
@@ -493,7 +515,8 @@ mod impl_ {
         Some(v) => v,
         None => {
           // Took more than a single read and some buffering.
-          simd_json::from_slice(&mut self.buffer[..nread])?
+          simd_json::from_slice(&mut self.buffer[..nread])
+            .map_err(IpcJsonStreamError::SimdJson)?
         }
       };
 
diff --git a/ext/node/ops/os/mod.rs b/ext/node/ops/os/mod.rs
index ca91895f22..ea7e6b99fd 100644
--- a/ext/node/ops/os/mod.rs
+++ b/ext/node/ops/os/mod.rs
@@ -1,28 +1,42 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
+use std::mem::MaybeUninit;
+
 use crate::NodePermissions;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 
 mod cpus;
-mod priority;
+pub mod priority;
+
+#[derive(Debug, thiserror::Error)]
+pub enum OsError {
+  #[error(transparent)]
+  Priority(priority::PriorityError),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error("Failed to get cpu info")]
+  FailedToGetCpuInfo,
+  #[error("Failed to get user info")]
+  FailedToGetUserInfo(#[source] std::io::Error),
+}
 
 #[op2(fast)]
 pub fn op_node_os_get_priority<P>(
   state: &mut OpState,
   pid: u32,
-) -> Result<i32, AnyError>
+) -> Result<i32, OsError>
 where
   P: NodePermissions + 'static,
 {
   {
     let permissions = state.borrow_mut::<P>();
-    permissions.check_sys("getPriority", "node:os.getPriority()")?;
+    permissions
+      .check_sys("getPriority", "node:os.getPriority()")
+      .map_err(OsError::Permission)?;
   }
 
-  priority::get_priority(pid)
+  priority::get_priority(pid).map_err(OsError::Priority)
 }
 
 #[op2(fast)]
@@ -30,34 +44,182 @@ pub fn op_node_os_set_priority<P>(
   state: &mut OpState,
   pid: u32,
   priority: i32,
-) -> Result<(), AnyError>
+) -> Result<(), OsError>
 where
   P: NodePermissions + 'static,
 {
   {
     let permissions = state.borrow_mut::<P>();
-    permissions.check_sys("setPriority", "node:os.setPriority()")?;
+    permissions
+      .check_sys("setPriority", "node:os.setPriority()")
+      .map_err(OsError::Permission)?;
   }
 
-  priority::set_priority(pid, priority)
+  priority::set_priority(pid, priority).map_err(OsError::Priority)
+}
+
+#[derive(serde::Serialize)]
+pub struct UserInfo {
+  username: String,
+  homedir: String,
+  shell: Option<String>,
+}
+
+#[cfg(unix)]
+fn get_user_info(uid: u32) -> Result<UserInfo, OsError> {
+  use std::ffi::CStr;
+  let mut pw: MaybeUninit<libc::passwd> = MaybeUninit::uninit();
+  let mut result: *mut libc::passwd = std::ptr::null_mut();
+  // SAFETY: libc call, no invariants
+  let max_buf_size = unsafe { libc::sysconf(libc::_SC_GETPW_R_SIZE_MAX) };
+  let buf_size = if max_buf_size < 0 {
+    // from the man page
+    16_384
+  } else {
+    max_buf_size as usize
+  };
+  let mut buf = {
+    let mut b = Vec::<MaybeUninit<libc::c_char>>::with_capacity(buf_size);
+    // SAFETY: MaybeUninit has no initialization invariants, and len == cap
+    unsafe {
+      b.set_len(buf_size);
+    }
+    b
+  };
+  // SAFETY: libc call, args are correct
+  let s = unsafe {
+    libc::getpwuid_r(
+      uid,
+      pw.as_mut_ptr(),
+      buf.as_mut_ptr().cast(),
+      buf_size,
+      std::ptr::addr_of_mut!(result),
+    )
+  };
+  if result.is_null() {
+    if s != 0 {
+      return Err(
+        OsError::FailedToGetUserInfo(std::io::Error::last_os_error()),
+      );
+    } else {
+      return Err(OsError::FailedToGetUserInfo(std::io::Error::from(
+        std::io::ErrorKind::NotFound,
+      )));
+    }
+  }
+  // SAFETY: pw was initialized by the call to `getpwuid_r` above
+  let pw = unsafe { pw.assume_init() };
+  // SAFETY: initialized above, pw alive until end of function, nul terminated
+  let username = unsafe { CStr::from_ptr(pw.pw_name) };
+  // SAFETY: initialized above, pw alive until end of function, nul terminated
+  let homedir = unsafe { CStr::from_ptr(pw.pw_dir) };
+  // SAFETY: initialized above, pw alive until end of function, nul terminated
+  let shell = unsafe { CStr::from_ptr(pw.pw_shell) };
+  Ok(UserInfo {
+    username: username.to_string_lossy().into_owned(),
+    homedir: homedir.to_string_lossy().into_owned(),
+    shell: Some(shell.to_string_lossy().into_owned()),
+  })
+}
+
+#[cfg(windows)]
+fn get_user_info(_uid: u32) -> Result<UserInfo, OsError> {
+  use std::ffi::OsString;
+  use std::os::windows::ffi::OsStringExt;
+
+  use windows_sys::Win32::Foundation::CloseHandle;
+  use windows_sys::Win32::Foundation::GetLastError;
+  use windows_sys::Win32::Foundation::ERROR_INSUFFICIENT_BUFFER;
+  use windows_sys::Win32::Foundation::HANDLE;
+  use windows_sys::Win32::System::Threading::GetCurrentProcess;
+  use windows_sys::Win32::System::Threading::OpenProcessToken;
+  use windows_sys::Win32::UI::Shell::GetUserProfileDirectoryW;
+  struct Handle(HANDLE);
+  impl Drop for Handle {
+    fn drop(&mut self) {
+      // SAFETY: win32 call
+      unsafe {
+        CloseHandle(self.0);
+      }
+    }
+  }
+  let mut token: MaybeUninit<HANDLE> = MaybeUninit::uninit();
+
+  // Get a handle to the current process
+  // SAFETY: win32 call
+  unsafe {
+    if OpenProcessToken(
+      GetCurrentProcess(),
+      windows_sys::Win32::Security::TOKEN_READ,
+      token.as_mut_ptr(),
+    ) == 0
+    {
+      return Err(
+        OsError::FailedToGetUserInfo(std::io::Error::last_os_error()),
+      );
+    }
+  }
+
+  // SAFETY: initialized by call above
+  let token = Handle(unsafe { token.assume_init() });
+
+  let mut bufsize = 0;
+  // get the size for the homedir buf (it'll end up in `bufsize`)
+  // SAFETY: win32 call
+  unsafe {
+    GetUserProfileDirectoryW(token.0, std::ptr::null_mut(), &mut bufsize);
+    let err = GetLastError();
+    if err != ERROR_INSUFFICIENT_BUFFER {
+      return Err(OsError::FailedToGetUserInfo(
+        std::io::Error::from_raw_os_error(err as i32),
+      ));
+    }
+  }
+  let mut path = vec![0; bufsize as usize];
+  // Actually get the homedir
+  // SAFETY: path is `bufsize` elements
+  unsafe {
+    if GetUserProfileDirectoryW(token.0, path.as_mut_ptr(), &mut bufsize) == 0 {
+      return Err(
+        OsError::FailedToGetUserInfo(std::io::Error::last_os_error()),
+      );
+    }
+  }
+  // remove trailing nul
+  path.pop();
+  let homedir_wide = OsString::from_wide(&path);
+  let homedir = homedir_wide.to_string_lossy().into_owned();
+
+  Ok(UserInfo {
+    username: deno_whoami::username(),
+    homedir,
+    shell: None,
+  })
 }
 
 #[op2]
-#[string]
-pub fn op_node_os_username<P>(state: &mut OpState) -> Result<String, AnyError>
+#[serde]
+pub fn op_node_os_user_info<P>(
+  state: &mut OpState,
+  #[smi] uid: u32,
+) -> Result<UserInfo, OsError>
 where
   P: NodePermissions + 'static,
 {
   {
     let permissions = state.borrow_mut::<P>();
-    permissions.check_sys("username", "node:os.userInfo()")?;
+    permissions
+      .check_sys("userInfo", "node:os.userInfo()")
+      .map_err(OsError::Permission)?;
   }
 
-  Ok(deno_whoami::username())
+  get_user_info(uid)
 }
 
 #[op2(fast)]
-pub fn op_geteuid<P>(state: &mut OpState) -> Result<u32, AnyError>
+pub fn op_geteuid<P>(
+  state: &mut OpState,
+) -> Result<u32, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
@@ -76,7 +238,9 @@ where
 }
 
 #[op2(fast)]
-pub fn op_getegid<P>(state: &mut OpState) -> Result<u32, AnyError>
+pub fn op_getegid<P>(
+  state: &mut OpState,
+) -> Result<u32, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
@@ -96,21 +260,25 @@ where
 
 #[op2]
 #[serde]
-pub fn op_cpus<P>(state: &mut OpState) -> Result<Vec<cpus::CpuInfo>, AnyError>
+pub fn op_cpus<P>(state: &mut OpState) -> Result<Vec<cpus::CpuInfo>, OsError>
 where
   P: NodePermissions + 'static,
 {
   {
     let permissions = state.borrow_mut::<P>();
-    permissions.check_sys("cpus", "node:os.cpus()")?;
+    permissions
+      .check_sys("cpus", "node:os.cpus()")
+      .map_err(OsError::Permission)?;
   }
 
-  cpus::cpu_info().ok_or_else(|| type_error("Failed to get cpu info"))
+  cpus::cpu_info().ok_or(OsError::FailedToGetCpuInfo)
 }
 
 #[op2]
 #[string]
-pub fn op_homedir<P>(state: &mut OpState) -> Result<Option<String>, AnyError>
+pub fn op_homedir<P>(
+  state: &mut OpState,
+) -> Result<Option<String>, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
diff --git a/ext/node/ops/os/priority.rs b/ext/node/ops/os/priority.rs
index 043928e2a6..9a1ebcca70 100644
--- a/ext/node/ops/os/priority.rs
+++ b/ext/node/ops/os/priority.rs
@@ -1,12 +1,18 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
-
 pub use impl_::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum PriorityError {
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[cfg(windows)]
+  #[error("Invalid priority")]
+  InvalidPriority,
+}
+
 #[cfg(unix)]
 mod impl_ {
-  use super::*;
   use errno::errno;
   use errno::set_errno;
   use errno::Errno;
@@ -16,7 +22,7 @@ mod impl_ {
   const PRIORITY_HIGH: i32 = -14;
 
   // Ref: https://github.com/libuv/libuv/blob/55376b044b74db40772e8a6e24d67a8673998e02/src/unix/core.c#L1533-L1547
-  pub fn get_priority(pid: u32) -> Result<i32, AnyError> {
+  pub fn get_priority(pid: u32) -> Result<i32, super::PriorityError> {
     set_errno(Errno(0));
     match (
       // SAFETY: libc::getpriority is unsafe
@@ -29,7 +35,10 @@ mod impl_ {
     }
   }
 
-  pub fn set_priority(pid: u32, priority: i32) -> Result<(), AnyError> {
+  pub fn set_priority(
+    pid: u32,
+    priority: i32,
+  ) -> Result<(), super::PriorityError> {
     // SAFETY: libc::setpriority is unsafe
     match unsafe { libc::setpriority(PRIO_PROCESS, pid as id_t, priority) } {
       -1 => Err(std::io::Error::last_os_error().into()),
@@ -40,8 +49,6 @@ mod impl_ {
 
 #[cfg(windows)]
 mod impl_ {
-  use super::*;
-  use deno_core::error::type_error;
   use winapi::shared::minwindef::DWORD;
   use winapi::shared::minwindef::FALSE;
   use winapi::shared::ntdef::NULL;
@@ -67,7 +74,7 @@ mod impl_ {
   const PRIORITY_HIGHEST: i32 = -20;
 
   // Ported from: https://github.com/libuv/libuv/blob/a877ca2435134ef86315326ef4ef0c16bdbabf17/src/win/util.c#L1649-L1685
-  pub fn get_priority(pid: u32) -> Result<i32, AnyError> {
+  pub fn get_priority(pid: u32) -> Result<i32, super::PriorityError> {
     // SAFETY: Windows API calls
     unsafe {
       let handle = if pid == 0 {
@@ -95,7 +102,10 @@ mod impl_ {
   }
 
   // Ported from: https://github.com/libuv/libuv/blob/a877ca2435134ef86315326ef4ef0c16bdbabf17/src/win/util.c#L1688-L1719
-  pub fn set_priority(pid: u32, priority: i32) -> Result<(), AnyError> {
+  pub fn set_priority(
+    pid: u32,
+    priority: i32,
+  ) -> Result<(), super::PriorityError> {
     // SAFETY: Windows API calls
     unsafe {
       let handle = if pid == 0 {
@@ -109,7 +119,7 @@ mod impl_ {
         #[allow(clippy::manual_range_contains)]
         let priority_class =
           if priority < PRIORITY_HIGHEST || priority > PRIORITY_LOW {
-            return Err(type_error("Invalid priority"));
+            return Err(super::PriorityError::InvalidPriority);
           } else if priority < PRIORITY_HIGH {
             REALTIME_PRIORITY_CLASS
           } else if priority < PRIORITY_ABOVE_NORMAL {
diff --git a/ext/node/ops/process.rs b/ext/node/ops/process.rs
index 0992c46c62..282567226e 100644
--- a/ext/node/ops/process.rs
+++ b/ext/node/ops/process.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_permissions::PermissionsContainer;
@@ -51,7 +50,7 @@ pub fn op_node_process_kill(
   state: &mut OpState,
   #[smi] pid: i32,
   #[smi] sig: i32,
-) -> Result<i32, AnyError> {
+) -> Result<i32, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_run_all("process.kill")?;
diff --git a/ext/node/ops/require.rs b/ext/node/ops/require.rs
index 5473369815..30db8b6293 100644
--- a/ext/node/ops/require.rs
+++ b/ext/node/ops/require.rs
@@ -1,8 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::anyhow::Context;
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::url::Url;
 use deno_core::v8;
@@ -12,6 +9,7 @@ use deno_core::OpState;
 use deno_fs::FileSystemRc;
 use deno_package_json::PackageJsonRc;
 use deno_path_util::normalize_path;
+use deno_path_util::url_to_file_path;
 use node_resolver::NodeModuleKind;
 use node_resolver::NodeResolutionMode;
 use node_resolver::REQUIRE_CONDITIONS;
@@ -22,21 +20,52 @@ use std::path::PathBuf;
 use std::rc::Rc;
 
 use crate::NodePermissions;
-use crate::NodeRequireResolverRc;
+use crate::NodeRequireLoaderRc;
 use crate::NodeResolverRc;
 use crate::NpmResolverRc;
+use crate::PackageJsonResolverRc;
 
 #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
 fn ensure_read_permission<'a, P>(
   state: &mut OpState,
   file_path: &'a Path,
-) -> Result<Cow<'a, Path>, AnyError>
+) -> Result<Cow<'a, Path>, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
-  let resolver = state.borrow::<NodeRequireResolverRc>().clone();
+  let loader = state.borrow::<NodeRequireLoaderRc>().clone();
   let permissions = state.borrow_mut::<P>();
-  resolver.ensure_read_permission(permissions, file_path)
+  loader.ensure_read_permission(permissions, file_path)
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum RequireError {
+  #[error(transparent)]
+  UrlParse(#[from] url::ParseError),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  PackageExportsResolve(
+    #[from] node_resolver::errors::PackageExportsResolveError,
+  ),
+  #[error(transparent)]
+  PackageJsonLoad(#[from] node_resolver::errors::PackageJsonLoadError),
+  #[error(transparent)]
+  ClosestPkgJson(#[from] node_resolver::errors::ClosestPkgJsonError),
+  #[error(transparent)]
+  PackageImportsResolve(
+    #[from] node_resolver::errors::PackageImportsResolveError,
+  ),
+  #[error(transparent)]
+  FilePathConversion(#[from] deno_path_util::UrlToFilePathError),
+  #[error(transparent)]
+  UrlConversion(#[from] deno_path_util::PathToUrlError),
+  #[error(transparent)]
+  Fs(#[from] deno_io::fs::FsError),
+  #[error(transparent)]
+  ReadModule(deno_core::error::AnyError),
+  #[error("Unable to get CWD: {0}")]
+  UnableToGetCwd(deno_io::fs::FsError),
 }
 
 #[op2]
@@ -95,7 +124,7 @@ pub fn op_require_init_paths() -> Vec<String> {
 pub fn op_require_node_module_paths<P>(
   state: &mut OpState,
   #[string] from: String,
-) -> Result<Vec<String>, AnyError>
+) -> Result<Vec<String>, RequireError>
 where
   P: NodePermissions + 'static,
 {
@@ -104,13 +133,10 @@ where
   let from = if from.starts_with("file:///") {
     url_to_file_path(&Url::parse(&from)?)?
   } else {
-    let current_dir =
-      &(fs.cwd().map_err(AnyError::from)).context("Unable to get CWD")?;
-    deno_path_util::normalize_path(current_dir.join(from))
+    let current_dir = &fs.cwd().map_err(RequireError::UnableToGetCwd)?;
+    normalize_path(current_dir.join(from))
   };
 
-  let from = ensure_read_permission::<P>(state, &from)?;
-
   if cfg!(windows) {
     // return root node_modules when path is 'D:\\'.
     let from_str = from.to_str().unwrap();
@@ -131,7 +157,7 @@ where
   }
 
   let mut paths = Vec::with_capacity(from.components().count());
-  let mut current_path = from.as_ref();
+  let mut current_path = from.as_path();
   let mut maybe_parent = Some(current_path);
   while let Some(parent) = maybe_parent {
     if !parent.ends_with("node_modules") {
@@ -209,8 +235,11 @@ pub fn op_require_is_deno_dir_package(
   state: &mut OpState,
   #[string] path: String,
 ) -> bool {
-  let resolver = state.borrow::<NpmResolverRc>();
-  resolver.in_npm_package_at_file_path(&PathBuf::from(path))
+  let resolver = state.borrow::<NodeResolverRc>();
+  match deno_path_util::url_from_file_path(&PathBuf::from(path)) {
+    Ok(specifier) => resolver.in_npm_package(&specifier),
+    Err(_) => false,
+  }
 }
 
 #[op2]
@@ -264,7 +293,7 @@ pub fn op_require_path_is_absolute(#[string] p: String) -> bool {
 pub fn op_require_stat<P>(
   state: &mut OpState,
   #[string] path: String,
-) -> Result<i32, AnyError>
+) -> Result<i32, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
@@ -287,15 +316,16 @@ where
 pub fn op_require_real_path<P>(
   state: &mut OpState,
   #[string] request: String,
-) -> Result<String, AnyError>
+) -> Result<String, RequireError>
 where
   P: NodePermissions + 'static,
 {
   let path = PathBuf::from(request);
-  let path = ensure_read_permission::<P>(state, &path)?;
+  let path = ensure_read_permission::<P>(state, &path)
+    .map_err(RequireError::Permission)?;
   let fs = state.borrow::<FileSystemRc>();
   let canonicalized_path =
-    deno_core::strip_unc_prefix(fs.realpath_sync(&path)?);
+    deno_path_util::strip_unc_prefix(fs.realpath_sync(&path)?);
   Ok(canonicalized_path.to_string_lossy().into_owned())
 }
 
@@ -319,12 +349,14 @@ pub fn op_require_path_resolve(#[serde] parts: Vec<String>) -> String {
 #[string]
 pub fn op_require_path_dirname(
   #[string] request: String,
-) -> Result<String, AnyError> {
+) -> Result<String, deno_core::error::AnyError> {
   let p = PathBuf::from(request);
   if let Some(parent) = p.parent() {
     Ok(parent.to_string_lossy().into_owned())
   } else {
-    Err(generic_error("Path doesn't have a parent"))
+    Err(deno_core::error::generic_error(
+      "Path doesn't have a parent",
+    ))
   }
 }
 
@@ -332,12 +364,14 @@ pub fn op_require_path_dirname(
 #[string]
 pub fn op_require_path_basename(
   #[string] request: String,
-) -> Result<String, AnyError> {
+) -> Result<String, deno_core::error::AnyError> {
   let p = PathBuf::from(request);
   if let Some(path) = p.file_name() {
     Ok(path.to_string_lossy().into_owned())
   } else {
-    Err(generic_error("Path doesn't have a file name"))
+    Err(deno_core::error::generic_error(
+      "Path doesn't have a file name",
+    ))
   }
 }
 
@@ -348,7 +382,7 @@ pub fn op_require_try_self_parent_path<P>(
   has_parent: bool,
   #[string] maybe_parent_filename: Option<String>,
   #[string] maybe_parent_id: Option<String>,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
@@ -378,7 +412,7 @@ pub fn op_require_try_self<P>(
   state: &mut OpState,
   #[string] parent_path: Option<String>,
   #[string] request: String,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, RequireError>
 where
   P: NodePermissions + 'static,
 {
@@ -386,8 +420,8 @@ where
     return Ok(None);
   }
 
-  let node_resolver = state.borrow::<NodeResolverRc>();
-  let pkg = node_resolver
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
+  let pkg = pkg_json_resolver
     .get_closest_package_json_from_path(&PathBuf::from(parent_path.unwrap()))
     .ok()
     .flatten();
@@ -416,6 +450,7 @@ where
 
   let referrer = deno_core::url::Url::from_file_path(&pkg.path).unwrap();
   if let Some(exports) = &pkg.exports {
+    let node_resolver = state.borrow::<NodeResolverRc>();
     let r = node_resolver.package_exports_resolve(
       &pkg.path,
       &expansion,
@@ -440,14 +475,18 @@ where
 pub fn op_require_read_file<P>(
   state: &mut OpState,
   #[string] file_path: String,
-) -> Result<String, AnyError>
+) -> Result<String, RequireError>
 where
   P: NodePermissions + 'static,
 {
   let file_path = PathBuf::from(file_path);
-  let file_path = ensure_read_permission::<P>(state, &file_path)?;
-  let fs = state.borrow::<FileSystemRc>();
-  Ok(fs.read_text_file_lossy_sync(&file_path, None)?)
+  // todo(dsherret): there's multiple borrows to NodeRequireLoaderRc here
+  let file_path = ensure_read_permission::<P>(state, &file_path)
+    .map_err(RequireError::Permission)?;
+  let loader = state.borrow::<NodeRequireLoaderRc>();
+  loader
+    .load_text_file_lossy(&file_path)
+    .map_err(RequireError::ReadModule)
 }
 
 #[op2]
@@ -472,16 +511,17 @@ pub fn op_require_resolve_exports<P>(
   #[string] name: String,
   #[string] expansion: String,
   #[string] parent_path: String,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, RequireError>
 where
   P: NodePermissions + 'static,
 {
   let fs = state.borrow::<FileSystemRc>();
-  let npm_resolver = state.borrow::<NpmResolverRc>();
   let node_resolver = state.borrow::<NodeResolverRc>();
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
 
   let modules_path = PathBuf::from(&modules_path_str);
-  let pkg_path = if npm_resolver.in_npm_package_at_file_path(&modules_path)
+  let modules_specifier = deno_path_util::url_from_file_path(&modules_path)?;
+  let pkg_path = if node_resolver.in_npm_package(&modules_specifier)
     && !uses_local_node_modules_dir
   {
     modules_path
@@ -495,7 +535,7 @@ where
     }
   };
   let Some(pkg) =
-    node_resolver.load_package_json(&pkg_path.join("package.json"))?
+    pkg_json_resolver.load_package_json(&pkg_path.join("package.json"))?
   else {
     return Ok(None);
   };
@@ -503,12 +543,16 @@ where
     return Ok(None);
   };
 
-  let referrer = Url::from_file_path(parent_path).unwrap();
+  let referrer = if parent_path.is_empty() {
+    None
+  } else {
+    Some(Url::from_file_path(parent_path).unwrap())
+  };
   let r = node_resolver.package_exports_resolve(
     &pkg.path,
     &format!(".{expansion}"),
     exports,
-    Some(&referrer),
+    referrer.as_ref(),
     NodeModuleKind::Cjs,
     REQUIRE_CONDITIONS,
     NodeResolutionMode::Execution,
@@ -525,16 +569,14 @@ where
 pub fn op_require_read_closest_package_json<P>(
   state: &mut OpState,
   #[string] filename: String,
-) -> Result<Option<PackageJsonRc>, AnyError>
+) -> Result<Option<PackageJsonRc>, node_resolver::errors::ClosestPkgJsonError>
 where
   P: NodePermissions + 'static,
 {
   let filename = PathBuf::from(filename);
   // permissions: allow reading the closest package.json files
-  let node_resolver = state.borrow::<NodeResolverRc>().clone();
-  node_resolver
-    .get_closest_package_json_from_path(&filename)
-    .map_err(AnyError::from)
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
+  pkg_json_resolver.get_closest_package_json_from_path(&filename)
 }
 
 #[op2]
@@ -546,13 +588,13 @@ pub fn op_require_read_package_scope<P>(
 where
   P: NodePermissions + 'static,
 {
-  let node_resolver = state.borrow::<NodeResolverRc>().clone();
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
   let package_json_path = PathBuf::from(package_json_path);
   if package_json_path.file_name() != Some("package.json".as_ref()) {
     // permissions: do not allow reading a non-package.json file
     return None;
   }
-  node_resolver
+  pkg_json_resolver
     .load_package_json(&package_json_path)
     .ok()
     .flatten()
@@ -564,22 +606,23 @@ pub fn op_require_package_imports_resolve<P>(
   state: &mut OpState,
   #[string] referrer_filename: String,
   #[string] request: String,
-) -> Result<Option<String>, AnyError>
+) -> Result<Option<String>, RequireError>
 where
   P: NodePermissions + 'static,
 {
   let referrer_path = PathBuf::from(&referrer_filename);
-  let referrer_path = ensure_read_permission::<P>(state, &referrer_path)?;
-  let node_resolver = state.borrow::<NodeResolverRc>();
+  let referrer_path = ensure_read_permission::<P>(state, &referrer_path)
+    .map_err(RequireError::Permission)?;
+  let pkg_json_resolver = state.borrow::<PackageJsonResolverRc>();
   let Some(pkg) =
-    node_resolver.get_closest_package_json_from_path(&referrer_path)?
+    pkg_json_resolver.get_closest_package_json_from_path(&referrer_path)?
   else {
     return Ok(None);
   };
 
   if pkg.imports.is_some() {
-    let referrer_url =
-      deno_core::url::Url::from_file_path(&referrer_filename).unwrap();
+    let node_resolver = state.borrow::<NodeResolverRc>();
+    let referrer_url = Url::from_file_path(&referrer_filename).unwrap();
     let url = node_resolver.package_imports_resolve(
       &request,
       Some(&referrer_url),
@@ -604,20 +647,11 @@ pub fn op_require_break_on_next_statement(state: Rc<RefCell<OpState>>) {
   inspector.wait_for_session_and_break_on_next_statement()
 }
 
-fn url_to_file_path_string(url: &Url) -> Result<String, AnyError> {
+fn url_to_file_path_string(url: &Url) -> Result<String, RequireError> {
   let file_path = url_to_file_path(url)?;
   Ok(file_path.to_string_lossy().into_owned())
 }
 
-fn url_to_file_path(url: &Url) -> Result<PathBuf, AnyError> {
-  match url.to_file_path() {
-    Ok(file_path) => Ok(file_path),
-    Err(()) => {
-      deno_core::anyhow::bail!("failed to convert '{}' to file path", url)
-    }
-  }
-}
-
 #[op2(fast)]
 pub fn op_require_can_parse_as_esm(
   scope: &mut v8::HandleScope,
diff --git a/ext/node/ops/util.rs b/ext/node/ops/util.rs
index 533d51c92c..1c177ac043 100644
--- a/ext/node/ops/util.rs
+++ b/ext/node/ops/util.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::ResourceHandle;
@@ -22,7 +21,7 @@ enum HandleType {
 pub fn op_node_guess_handle_type(
   state: &mut OpState,
   rid: u32,
-) -> Result<u32, AnyError> {
+) -> Result<u32, deno_core::error::AnyError> {
   let handle = state.resource_table.get_handle(rid)?;
 
   let handle_type = match handle {
diff --git a/ext/node/ops/v8.rs b/ext/node/ops/v8.rs
index 8813d2e18e..61f67f11f7 100644
--- a/ext/node/ops/v8.rs
+++ b/ext/node/ops/v8.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_core::error::generic_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
+
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::FastString;
@@ -206,10 +204,9 @@ pub fn op_v8_write_value(
   scope: &mut v8::HandleScope,
   #[cppgc] ser: &Serializer,
   value: v8::Local<v8::Value>,
-) -> Result<(), AnyError> {
+) {
   let context = scope.get_current_context();
   ser.inner.write_value(context, value);
-  Ok(())
 }
 
 struct DeserBuffer {
@@ -271,11 +268,13 @@ pub fn op_v8_new_deserializer(
   scope: &mut v8::HandleScope,
   obj: v8::Local<v8::Object>,
   buffer: v8::Local<v8::ArrayBufferView>,
-) -> Result<Deserializer<'static>, AnyError> {
+) -> Result<Deserializer<'static>, deno_core::error::AnyError> {
   let offset = buffer.byte_offset();
   let len = buffer.byte_length();
   let backing_store = buffer.get_backing_store().ok_or_else(|| {
-    generic_error("deserialization buffer has no backing store")
+    deno_core::error::generic_error(
+      "deserialization buffer has no backing store",
+    )
   })?;
   let (buf_slice, buf_ptr) = if let Some(data) = backing_store.data() {
     // SAFETY: the offset is valid for the underlying buffer because we're getting it directly from v8
@@ -317,10 +316,10 @@ pub fn op_v8_transfer_array_buffer_de(
 #[op2(fast)]
 pub fn op_v8_read_double(
   #[cppgc] deser: &Deserializer,
-) -> Result<f64, AnyError> {
+) -> Result<f64, deno_core::error::AnyError> {
   let mut double = 0f64;
   if !deser.inner.read_double(&mut double) {
-    return Err(type_error("ReadDouble() failed"));
+    return Err(deno_core::error::type_error("ReadDouble() failed"));
   }
   Ok(double)
 }
@@ -355,10 +354,10 @@ pub fn op_v8_read_raw_bytes(
 #[op2(fast)]
 pub fn op_v8_read_uint32(
   #[cppgc] deser: &Deserializer,
-) -> Result<u32, AnyError> {
+) -> Result<u32, deno_core::error::AnyError> {
   let mut value = 0;
   if !deser.inner.read_uint32(&mut value) {
-    return Err(type_error("ReadUint32() failed"));
+    return Err(deno_core::error::type_error("ReadUint32() failed"));
   }
 
   Ok(value)
@@ -368,10 +367,10 @@ pub fn op_v8_read_uint32(
 #[serde]
 pub fn op_v8_read_uint64(
   #[cppgc] deser: &Deserializer,
-) -> Result<(u32, u32), AnyError> {
+) -> Result<(u32, u32), deno_core::error::AnyError> {
   let mut val = 0;
   if !deser.inner.read_uint64(&mut val) {
-    return Err(type_error("ReadUint64() failed"));
+    return Err(deno_core::error::type_error("ReadUint64() failed"));
   }
 
   Ok(((val >> 32) as u32, val as u32))
diff --git a/ext/node/ops/winerror.rs b/ext/node/ops/winerror.rs
index c0d66f7d0b..cb053774ef 100644
--- a/ext/node/ops/winerror.rs
+++ b/ext/node/ops/winerror.rs
@@ -62,10 +62,11 @@ pub fn op_node_sys_to_uv_error(err: i32) -> String {
     WSAEHOSTUNREACH => "EHOSTUNREACH",
     ERROR_INSUFFICIENT_BUFFER => "EINVAL",
     ERROR_INVALID_DATA => "EINVAL",
-    ERROR_INVALID_NAME => "EINVAL",
+    ERROR_INVALID_NAME => "ENOENT",
     ERROR_INVALID_PARAMETER => "EINVAL",
     WSAEINVAL => "EINVAL",
     WSAEPFNOSUPPORT => "EINVAL",
+    ERROR_NOT_A_REPARSE_POINT => "EINVAL",
     ERROR_BEGINNING_OF_MEDIA => "EIO",
     ERROR_BUS_RESET => "EIO",
     ERROR_CRC => "EIO",
diff --git a/ext/node/ops/worker_threads.rs b/ext/node/ops/worker_threads.rs
index 4c50092f28..d2e5758826 100644
--- a/ext/node/ops/worker_threads.rs
+++ b/ext/node/ops/worker_threads.rs
@@ -1,39 +1,56 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::generic_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::url::Url;
 use deno_core::OpState;
 use deno_fs::FileSystemRc;
-use node_resolver::NodeResolution;
 use std::borrow::Cow;
 use std::path::Path;
 use std::path::PathBuf;
 
 use crate::NodePermissions;
-use crate::NodeRequireResolverRc;
-use crate::NodeResolverRc;
+use crate::NodeRequireLoaderRc;
 
 #[must_use = "the resolved return value to mitigate time-of-check to time-of-use issues"]
 fn ensure_read_permission<'a, P>(
   state: &mut OpState,
   file_path: &'a Path,
-) -> Result<Cow<'a, Path>, AnyError>
+) -> Result<Cow<'a, Path>, deno_core::error::AnyError>
 where
   P: NodePermissions + 'static,
 {
-  let resolver = state.borrow::<NodeRequireResolverRc>().clone();
+  let loader = state.borrow::<NodeRequireLoaderRc>().clone();
   let permissions = state.borrow_mut::<P>();
-  resolver.ensure_read_permission(permissions, file_path)
+  loader.ensure_read_permission(permissions, file_path)
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum WorkerThreadsFilenameError {
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error("{0}")]
+  UrlParse(#[from] url::ParseError),
+  #[error("Relative path entries must start with '.' or '..'")]
+  InvalidRelativeUrl,
+  #[error("URL from Path-String")]
+  UrlFromPathString,
+  #[error("URL to Path-String")]
+  UrlToPathString,
+  #[error("URL to Path")]
+  UrlToPath,
+  #[error("File not found [{0:?}]")]
+  FileNotFound(PathBuf),
+  #[error(transparent)]
+  Fs(#[from] deno_io::fs::FsError),
+}
+
+// todo(dsherret): we should remove this and do all this work inside op_create_worker
 #[op2]
 #[string]
 pub fn op_worker_threads_filename<P>(
   state: &mut OpState,
   #[string] specifier: String,
-) -> Result<String, AnyError>
+) -> Result<String, WorkerThreadsFilenameError>
 where
   P: NodePermissions + 'static,
 {
@@ -45,44 +62,26 @@ where
   } else {
     let path = PathBuf::from(&specifier);
     if path.is_relative() && !specifier.starts_with('.') {
-      return Err(generic_error(
-        "Relative path entries must start with '.' or '..'",
-      ));
+      return Err(WorkerThreadsFilenameError::InvalidRelativeUrl);
     }
-    let path = ensure_read_permission::<P>(state, &path)?;
+    let path = ensure_read_permission::<P>(state, &path)
+      .map_err(WorkerThreadsFilenameError::Permission)?;
     let fs = state.borrow::<FileSystemRc>();
     let canonicalized_path =
-      deno_core::strip_unc_prefix(fs.realpath_sync(&path)?);
+      deno_path_util::strip_unc_prefix(fs.realpath_sync(&path)?);
     Url::from_file_path(canonicalized_path)
-      .map_err(|e| generic_error(format!("URL from Path-String: {:#?}", e)))?
+      .map_err(|_| WorkerThreadsFilenameError::UrlFromPathString)?
   };
   let url_path = url
     .to_file_path()
-    .map_err(|e| generic_error(format!("URL to Path-String: {:#?}", e)))?;
-  let url_path = ensure_read_permission::<P>(state, &url_path)?;
+    .map_err(|_| WorkerThreadsFilenameError::UrlToPathString)?;
+  let url_path = ensure_read_permission::<P>(state, &url_path)
+    .map_err(WorkerThreadsFilenameError::Permission)?;
   let fs = state.borrow::<FileSystemRc>();
   if !fs.exists_sync(&url_path) {
-    return Err(generic_error(format!("File not found [{:?}]", url_path)));
-  }
-  let node_resolver = state.borrow::<NodeResolverRc>();
-  match node_resolver.url_to_node_resolution(url)? {
-    NodeResolution::Esm(u) => Ok(u.to_string()),
-    NodeResolution::CommonJs(u) => wrap_cjs(u),
-    NodeResolution::BuiltIn(_) => Err(generic_error("Neither ESM nor CJS")),
+    return Err(WorkerThreadsFilenameError::FileNotFound(
+      url_path.to_path_buf(),
+    ));
   }
-}
-
-///
-/// Wrap a CJS file-URL and the required setup in a stringified `data:`-URL
-///
-fn wrap_cjs(url: Url) -> Result<String, AnyError> {
-  let path = url
-    .to_file_path()
-    .map_err(|e| generic_error(format!("URL to Path: {:#?}", e)))?;
-  let filename = path.file_name().unwrap().to_string_lossy();
-  Ok(format!(
-    "data:text/javascript,import {{ createRequire }} from \"node:module\";\
-    const require = createRequire(\"{}\"); require(\"./{}\");",
-    url, filename,
-  ))
+  Ok(url.to_string())
 }
diff --git a/ext/node/ops/zlib/brotli.rs b/ext/node/ops/zlib/brotli.rs
index 3e3905fc3d..1a681ff7f7 100644
--- a/ext/node/ops/zlib/brotli.rs
+++ b/ext/node/ops/zlib/brotli.rs
@@ -9,8 +9,6 @@ use brotli::BrotliDecompressStream;
 use brotli::BrotliResult;
 use brotli::BrotliState;
 use brotli::Decompressor;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::JsBuffer;
 use deno_core::OpState;
@@ -19,7 +17,23 @@ use deno_core::ToJsBuffer;
 use std::cell::RefCell;
 use std::io::Read;
 
-fn encoder_mode(mode: u32) -> Result<BrotliEncoderMode, AnyError> {
+#[derive(Debug, thiserror::Error)]
+pub enum BrotliError {
+  #[error("Invalid encoder mode")]
+  InvalidEncoderMode,
+  #[error("Failed to compress")]
+  CompressFailed,
+  #[error("Failed to decompress")]
+  DecompressFailed,
+  #[error(transparent)]
+  Join(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(std::io::Error),
+}
+
+fn encoder_mode(mode: u32) -> Result<BrotliEncoderMode, BrotliError> {
   Ok(match mode {
     0 => BrotliEncoderMode::BROTLI_MODE_GENERIC,
     1 => BrotliEncoderMode::BROTLI_MODE_TEXT,
@@ -28,7 +42,7 @@ fn encoder_mode(mode: u32) -> Result<BrotliEncoderMode, AnyError> {
     4 => BrotliEncoderMode::BROTLI_FORCE_MSB_PRIOR,
     5 => BrotliEncoderMode::BROTLI_FORCE_UTF8_PRIOR,
     6 => BrotliEncoderMode::BROTLI_FORCE_SIGNED_PRIOR,
-    _ => return Err(type_error("Invalid encoder mode")),
+    _ => return Err(BrotliError::InvalidEncoderMode),
   })
 }
 
@@ -40,7 +54,7 @@ pub fn op_brotli_compress(
   #[smi] quality: i32,
   #[smi] lgwin: i32,
   #[smi] mode: u32,
-) -> Result<usize, AnyError> {
+) -> Result<usize, BrotliError> {
   let mode = encoder_mode(mode)?;
   let mut out_size = out.len();
 
@@ -57,7 +71,7 @@ pub fn op_brotli_compress(
     &mut |_, _, _, _| (),
   );
   if result != 1 {
-    return Err(type_error("Failed to compress"));
+    return Err(BrotliError::CompressFailed);
   }
 
   Ok(out_size)
@@ -87,7 +101,7 @@ pub async fn op_brotli_compress_async(
   #[smi] quality: i32,
   #[smi] lgwin: i32,
   #[smi] mode: u32,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, BrotliError> {
   let mode = encoder_mode(mode)?;
   tokio::task::spawn_blocking(move || {
     let input = &*input;
@@ -107,7 +121,7 @@ pub async fn op_brotli_compress_async(
       &mut |_, _, _, _| (),
     );
     if result != 1 {
-      return Err(type_error("Failed to compress"));
+      return Err(BrotliError::CompressFailed);
     }
 
     out.truncate(out_size);
@@ -151,8 +165,11 @@ pub fn op_brotli_compress_stream(
   #[smi] rid: u32,
   #[buffer] input: &[u8],
   #[buffer] output: &mut [u8],
-) -> Result<usize, AnyError> {
-  let ctx = state.resource_table.get::<BrotliCompressCtx>(rid)?;
+) -> Result<usize, BrotliError> {
+  let ctx = state
+    .resource_table
+    .get::<BrotliCompressCtx>(rid)
+    .map_err(BrotliError::Resource)?;
   let mut inst = ctx.inst.borrow_mut();
   let mut output_offset = 0;
 
@@ -168,7 +185,7 @@ pub fn op_brotli_compress_stream(
     &mut |_, _, _, _| (),
   );
   if !result {
-    return Err(type_error("Failed to compress"));
+    return Err(BrotliError::CompressFailed);
   }
 
   Ok(output_offset)
@@ -180,8 +197,11 @@ pub fn op_brotli_compress_stream_end(
   state: &mut OpState,
   #[smi] rid: u32,
   #[buffer] output: &mut [u8],
-) -> Result<usize, AnyError> {
-  let ctx = state.resource_table.get::<BrotliCompressCtx>(rid)?;
+) -> Result<usize, BrotliError> {
+  let ctx = state
+    .resource_table
+    .get::<BrotliCompressCtx>(rid)
+    .map_err(BrotliError::Resource)?;
   let mut inst = ctx.inst.borrow_mut();
   let mut output_offset = 0;
 
@@ -197,13 +217,13 @@ pub fn op_brotli_compress_stream_end(
     &mut |_, _, _, _| (),
   );
   if !result {
-    return Err(type_error("Failed to compress"));
+    return Err(BrotliError::CompressFailed);
   }
 
   Ok(output_offset)
 }
 
-fn brotli_decompress(buffer: &[u8]) -> Result<ToJsBuffer, AnyError> {
+fn brotli_decompress(buffer: &[u8]) -> Result<ToJsBuffer, std::io::Error> {
   let mut output = Vec::with_capacity(4096);
   let mut decompressor = Decompressor::new(buffer, buffer.len());
   decompressor.read_to_end(&mut output)?;
@@ -214,7 +234,7 @@ fn brotli_decompress(buffer: &[u8]) -> Result<ToJsBuffer, AnyError> {
 #[serde]
 pub fn op_brotli_decompress(
   #[buffer] buffer: &[u8],
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, std::io::Error> {
   brotli_decompress(buffer)
 }
 
@@ -222,8 +242,11 @@ pub fn op_brotli_decompress(
 #[serde]
 pub async fn op_brotli_decompress_async(
   #[buffer] buffer: JsBuffer,
-) -> Result<ToJsBuffer, AnyError> {
-  tokio::task::spawn_blocking(move || brotli_decompress(&buffer)).await?
+) -> Result<ToJsBuffer, BrotliError> {
+  tokio::task::spawn_blocking(move || {
+    brotli_decompress(&buffer).map_err(BrotliError::Io)
+  })
+  .await?
 }
 
 struct BrotliDecompressCtx {
@@ -252,8 +275,11 @@ pub fn op_brotli_decompress_stream(
   #[smi] rid: u32,
   #[buffer] input: &[u8],
   #[buffer] output: &mut [u8],
-) -> Result<usize, AnyError> {
-  let ctx = state.resource_table.get::<BrotliDecompressCtx>(rid)?;
+) -> Result<usize, BrotliError> {
+  let ctx = state
+    .resource_table
+    .get::<BrotliDecompressCtx>(rid)
+    .map_err(BrotliError::Resource)?;
   let mut inst = ctx.inst.borrow_mut();
   let mut output_offset = 0;
 
@@ -268,7 +294,7 @@ pub fn op_brotli_decompress_stream(
     &mut inst,
   );
   if matches!(result, BrotliResult::ResultFailure) {
-    return Err(type_error("Failed to decompress"));
+    return Err(BrotliError::DecompressFailed);
   }
 
   Ok(output_offset)
@@ -280,8 +306,11 @@ pub fn op_brotli_decompress_stream_end(
   state: &mut OpState,
   #[smi] rid: u32,
   #[buffer] output: &mut [u8],
-) -> Result<usize, AnyError> {
-  let ctx = state.resource_table.get::<BrotliDecompressCtx>(rid)?;
+) -> Result<usize, BrotliError> {
+  let ctx = state
+    .resource_table
+    .get::<BrotliDecompressCtx>(rid)
+    .map_err(BrotliError::Resource)?;
   let mut inst = ctx.inst.borrow_mut();
   let mut output_offset = 0;
 
@@ -296,7 +325,7 @@ pub fn op_brotli_decompress_stream_end(
     &mut inst,
   );
   if matches!(result, BrotliResult::ResultFailure) {
-    return Err(type_error("Failed to decompress"));
+    return Err(BrotliError::DecompressFailed);
   }
 
   Ok(output_offset)
diff --git a/ext/node/ops/zlib/mod.rs b/ext/node/ops/zlib/mod.rs
index b1d6d21d22..e75ef050d2 100644
--- a/ext/node/ops/zlib/mod.rs
+++ b/ext/node/ops/zlib/mod.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
+
 use deno_core::op2;
 use std::borrow::Cow;
 use std::cell::RefCell;
@@ -8,7 +7,7 @@ use zlib::*;
 
 mod alloc;
 pub mod brotli;
-mod mode;
+pub mod mode;
 mod stream;
 
 use mode::Flush;
@@ -17,11 +16,11 @@ use mode::Mode;
 use self::stream::StreamWrapper;
 
 #[inline]
-fn check(condition: bool, msg: &str) -> Result<(), AnyError> {
+fn check(condition: bool, msg: &str) -> Result<(), deno_core::error::AnyError> {
   if condition {
     Ok(())
   } else {
-    Err(type_error(msg.to_string()))
+    Err(deno_core::error::type_error(msg.to_string()))
   }
 }
 
@@ -56,7 +55,7 @@ impl ZlibInner {
     out_off: u32,
     out_len: u32,
     flush: Flush,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), deno_core::error::AnyError> {
     check(self.init_done, "write before init")?;
     check(!self.write_in_progress, "write already in progress")?;
     check(!self.pending_close, "close already in progress")?;
@@ -65,11 +64,11 @@ impl ZlibInner {
 
     let next_in = input
       .get(in_off as usize..in_off as usize + in_len as usize)
-      .ok_or_else(|| type_error("invalid input range"))?
+      .ok_or_else(|| deno_core::error::type_error("invalid input range"))?
       .as_ptr() as *mut _;
     let next_out = out
       .get_mut(out_off as usize..out_off as usize + out_len as usize)
-      .ok_or_else(|| type_error("invalid output range"))?
+      .ok_or_else(|| deno_core::error::type_error("invalid output range"))?
       .as_mut_ptr();
 
     self.strm.avail_in = in_len;
@@ -81,7 +80,10 @@ impl ZlibInner {
     Ok(())
   }
 
-  fn do_write(&mut self, flush: Flush) -> Result<(), AnyError> {
+  fn do_write(
+    &mut self,
+    flush: Flush,
+  ) -> Result<(), deno_core::error::AnyError> {
     self.flush = flush;
     match self.mode {
       Mode::Deflate | Mode::Gzip | Mode::DeflateRaw => {
@@ -127,7 +129,7 @@ impl ZlibInner {
             self.mode = Mode::Inflate;
           }
         } else if next_expected_header_byte.is_some() {
-          return Err(type_error(
+          return Err(deno_core::error::type_error(
             "invalid number of gzip magic number bytes read",
           ));
         }
@@ -181,7 +183,7 @@ impl ZlibInner {
     Ok(())
   }
 
-  fn init_stream(&mut self) -> Result<(), AnyError> {
+  fn init_stream(&mut self) -> Result<(), deno_core::error::AnyError> {
     match self.mode {
       Mode::Gzip | Mode::Gunzip => self.window_bits += 16,
       Mode::Unzip => self.window_bits += 32,
@@ -199,7 +201,7 @@ impl ZlibInner {
       Mode::Inflate | Mode::Gunzip | Mode::InflateRaw | Mode::Unzip => {
         self.strm.inflate_init(self.window_bits)
       }
-      Mode::None => return Err(type_error("Unknown mode")),
+      Mode::None => return Err(deno_core::error::type_error("Unknown mode")),
     };
 
     self.write_in_progress = false;
@@ -208,7 +210,7 @@ impl ZlibInner {
     Ok(())
   }
 
-  fn close(&mut self) -> Result<bool, AnyError> {
+  fn close(&mut self) -> Result<bool, deno_core::error::AnyError> {
     if self.write_in_progress {
       self.pending_close = true;
       return Ok(false);
@@ -222,10 +224,8 @@ impl ZlibInner {
     Ok(true)
   }
 
-  fn reset_stream(&mut self) -> Result<(), AnyError> {
+  fn reset_stream(&mut self) {
     self.err = self.strm.reset(self.mode);
-
-    Ok(())
   }
 }
 
@@ -243,7 +243,7 @@ impl deno_core::Resource for Zlib {
 
 #[op2]
 #[cppgc]
-pub fn op_zlib_new(#[smi] mode: i32) -> Result<Zlib, AnyError> {
+pub fn op_zlib_new(#[smi] mode: i32) -> Result<Zlib, mode::ModeError> {
   let mode = Mode::try_from(mode)?;
 
   let inner = ZlibInner {
@@ -256,12 +256,20 @@ pub fn op_zlib_new(#[smi] mode: i32) -> Result<Zlib, AnyError> {
   })
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum ZlibError {
+  #[error("zlib not initialized")]
+  NotInitialized,
+  #[error(transparent)]
+  Mode(#[from] mode::ModeError),
+  #[error(transparent)]
+  Other(#[from] deno_core::error::AnyError),
+}
+
 #[op2(fast)]
-pub fn op_zlib_close(#[cppgc] resource: &Zlib) -> Result<(), AnyError> {
+pub fn op_zlib_close(#[cppgc] resource: &Zlib) -> Result<(), ZlibError> {
   let mut resource = resource.inner.borrow_mut();
-  let zlib = resource
-    .as_mut()
-    .ok_or_else(|| type_error("zlib not initialized"))?;
+  let zlib = resource.as_mut().ok_or(ZlibError::NotInitialized)?;
 
   // If there is a pending write, defer the close until the write is done.
   zlib.close()?;
@@ -282,11 +290,9 @@ pub fn op_zlib_write(
   #[smi] out_off: u32,
   #[smi] out_len: u32,
   #[buffer] result: &mut [u32],
-) -> Result<i32, AnyError> {
+) -> Result<i32, ZlibError> {
   let mut zlib = resource.inner.borrow_mut();
-  let zlib = zlib
-    .as_mut()
-    .ok_or_else(|| type_error("zlib not initialized"))?;
+  let zlib = zlib.as_mut().ok_or(ZlibError::NotInitialized)?;
 
   let flush = Flush::try_from(flush)?;
   zlib.start_write(input, in_off, in_len, out, out_off, out_len, flush)?;
@@ -307,11 +313,9 @@ pub fn op_zlib_init(
   #[smi] mem_level: i32,
   #[smi] strategy: i32,
   #[buffer] dictionary: &[u8],
-) -> Result<i32, AnyError> {
+) -> Result<i32, ZlibError> {
   let mut zlib = resource.inner.borrow_mut();
-  let zlib = zlib
-    .as_mut()
-    .ok_or_else(|| type_error("zlib not initialized"))?;
+  let zlib = zlib.as_mut().ok_or(ZlibError::NotInitialized)?;
 
   check((8..=15).contains(&window_bits), "invalid windowBits")?;
   check((-1..=9).contains(&level), "invalid level")?;
@@ -348,13 +352,11 @@ pub fn op_zlib_init(
 
 #[op2(fast)]
 #[smi]
-pub fn op_zlib_reset(#[cppgc] resource: &Zlib) -> Result<i32, AnyError> {
+pub fn op_zlib_reset(#[cppgc] resource: &Zlib) -> Result<i32, ZlibError> {
   let mut zlib = resource.inner.borrow_mut();
-  let zlib = zlib
-    .as_mut()
-    .ok_or_else(|| type_error("zlib not initialized"))?;
+  let zlib = zlib.as_mut().ok_or(ZlibError::NotInitialized)?;
 
-  zlib.reset_stream()?;
+  zlib.reset_stream();
 
   Ok(zlib.err)
 }
@@ -362,12 +364,10 @@ pub fn op_zlib_reset(#[cppgc] resource: &Zlib) -> Result<i32, AnyError> {
 #[op2(fast)]
 pub fn op_zlib_close_if_pending(
   #[cppgc] resource: &Zlib,
-) -> Result<(), AnyError> {
+) -> Result<(), ZlibError> {
   let pending_close = {
     let mut zlib = resource.inner.borrow_mut();
-    let zlib = zlib
-      .as_mut()
-      .ok_or_else(|| type_error("zlib not initialized"))?;
+    let zlib = zlib.as_mut().ok_or(ZlibError::NotInitialized)?;
 
     zlib.write_in_progress = false;
     zlib.pending_close
diff --git a/ext/node/ops/zlib/mode.rs b/ext/node/ops/zlib/mode.rs
index 753300cc49..41565f9b11 100644
--- a/ext/node/ops/zlib/mode.rs
+++ b/ext/node/ops/zlib/mode.rs
@@ -1,19 +1,8 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-#[derive(Debug)]
-pub enum Error {
-  BadArgument,
-}
-
-impl std::fmt::Display for Error {
-  fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
-    match self {
-      Error::BadArgument => write!(f, "bad argument"),
-    }
-  }
-}
-
-impl std::error::Error for Error {}
+#[derive(Debug, thiserror::Error)]
+#[error("bad argument")]
+pub struct ModeError;
 
 macro_rules! repr_i32 {
     ($(#[$meta:meta])* $vis:vis enum $name:ident {
@@ -25,12 +14,12 @@ macro_rules! repr_i32 {
       }
 
       impl core::convert::TryFrom<i32> for $name {
-        type Error = Error;
+        type Error = ModeError;
 
         fn try_from(v: i32) -> Result<Self, Self::Error> {
           match v {
             $(x if x == $name::$vname as i32 => Ok($name::$vname),)*
-            _ => Err(Error::BadArgument),
+            _ => Err(ModeError),
           }
         }
       }
diff --git a/ext/node/polyfills/01_require.js b/ext/node/polyfills/01_require.js
index 5b0980c310..296d819aa5 100644
--- a/ext/node/polyfills/01_require.js
+++ b/ext/node/polyfills/01_require.js
@@ -523,17 +523,13 @@ function resolveExports(
     return;
   }
 
-  if (!parentPath) {
-    return false;
-  }
-
   return op_require_resolve_exports(
     usesLocalNodeModulesDir,
     modulesPath,
     request,
     name,
     expansion,
-    parentPath,
+    parentPath ?? "",
   ) ?? false;
 }
 
@@ -1075,13 +1071,35 @@ Module._extensions[".js"] = function (module, filename) {
     } else if (pkg?.type === "commonjs") {
       format = "commonjs";
     }
-  } else if (StringPrototypeEndsWith(filename, ".cjs")) {
-    format = "commonjs";
   }
 
   module._compile(content, filename, format);
 };
 
+Module._extensions[".ts"] =
+  Module._extensions[".jsx"] =
+  Module._extensions[".tsx"] =
+    function (module, filename) {
+      const content = op_require_read_file(filename);
+
+      let format;
+      const pkg = op_require_read_closest_package_json(filename);
+      if (pkg?.type === "module") {
+        format = "module";
+      } else if (pkg?.type === "commonjs") {
+        format = "commonjs";
+      }
+
+      module._compile(content, filename, format);
+    };
+
+Module._extensions[".cjs"] =
+  Module._extensions[".cts"] =
+    function (module, filename) {
+      const content = op_require_read_file(filename);
+      module._compile(content, filename, "commonjs");
+    };
+
 function loadESMFromCJS(module, filename, code) {
   const namespace = op_import_sync(
     url.pathToFileURL(filename).toString(),
@@ -1091,7 +1109,10 @@ function loadESMFromCJS(module, filename, code) {
   module.exports = namespace;
 }
 
-Module._extensions[".mjs"] = function (module, filename) {
+Module._extensions[".mjs"] = Module._extensions[".mts"] = function (
+  module,
+  filename,
+) {
   loadESMFromCJS(module, filename);
 };
 
diff --git a/ext/node/polyfills/_fs/_fs_copy.ts b/ext/node/polyfills/_fs/_fs_copy.ts
index 2f8ddf4fcd..0434bff4d1 100644
--- a/ext/node/polyfills/_fs/_fs_copy.ts
+++ b/ext/node/polyfills/_fs/_fs_copy.ts
@@ -53,8 +53,9 @@ export function copyFile(
     }, (e) => {
       if (e instanceof Deno.errors.NotFound) {
         Deno.copyFile(srcStr, destStr).then(() => cb(null), cb);
+      } else {
+        cb(e);
       }
-      cb(e);
     });
   } else {
     Deno.copyFile(srcStr, destStr).then(() => cb(null), cb);
@@ -83,8 +84,9 @@ export function copyFileSync(
     } catch (e) {
       if (e instanceof Deno.errors.NotFound) {
         Deno.copyFileSync(srcStr, destStr);
+      } else {
+        throw e;
       }
-      throw e;
     }
   } else {
     Deno.copyFileSync(srcStr, destStr);
diff --git a/ext/node/polyfills/_fs/_fs_readFile.ts b/ext/node/polyfills/_fs/_fs_readFile.ts
index 0f05ee1678..cf7e0305d8 100644
--- a/ext/node/polyfills/_fs/_fs_readFile.ts
+++ b/ext/node/polyfills/_fs/_fs_readFile.ts
@@ -19,6 +19,7 @@ import {
   TextEncodings,
 } from "ext:deno_node/_utils.ts";
 import { FsFile } from "ext:deno_fs/30_fs.js";
+import { denoErrorToNodeError } from "ext:deno_node/internal/errors.ts";
 
 function maybeDecode(data: Uint8Array, encoding: TextEncodings): string;
 function maybeDecode(
@@ -87,7 +88,7 @@ export function readFile(
       }
       const buffer = maybeDecode(data, encoding);
       (cb as BinaryCallback)(null, buffer);
-    }, (err) => cb && cb(err));
+    }, (err) => cb && cb(denoErrorToNodeError(err)));
   }
 }
 
@@ -117,7 +118,12 @@ export function readFileSync(
   opt?: FileOptionsArgument,
 ): string | Buffer {
   path = path instanceof URL ? pathFromURL(path) : path;
-  const data = Deno.readFileSync(path);
+  let data;
+  try {
+    data = Deno.readFileSync(path);
+  } catch (err) {
+    throw denoErrorToNodeError(err);
+  }
   const encoding = getEncoding(opt);
   if (encoding && encoding !== "binary") {
     const text = maybeDecode(data, encoding);
diff --git a/ext/node/polyfills/_fs/_fs_readlink.ts b/ext/node/polyfills/_fs/_fs_readlink.ts
index 5f23127982..08bea843fa 100644
--- a/ext/node/polyfills/_fs/_fs_readlink.ts
+++ b/ext/node/polyfills/_fs/_fs_readlink.ts
@@ -4,13 +4,10 @@
 // deno-lint-ignore-file prefer-primordials
 
 import { TextEncoder } from "ext:deno_web/08_text_encoding.js";
-import {
-  intoCallbackAPIWithIntercept,
-  MaybeEmpty,
-  notImplemented,
-} from "ext:deno_node/_utils.ts";
+import { MaybeEmpty, notImplemented } from "ext:deno_node/_utils.ts";
 import { pathFromURL } from "ext:deno_web/00_infra.js";
 import { promisify } from "ext:deno_node/internal/util.mjs";
+import { denoErrorToNodeError } from "ext:deno_node/internal/errors.ts";
 
 type ReadlinkCallback = (
   err: MaybeEmpty<Error>,
@@ -69,12 +66,17 @@ export function readlink(
 
   const encoding = getEncoding(optOrCallback);
 
-  intoCallbackAPIWithIntercept<string, Uint8Array | string>(
-    Deno.readLink,
-    (data: string): string | Uint8Array => maybeEncode(data, encoding),
-    cb,
-    path,
-  );
+  Deno.readLink(path).then((data: string) => {
+    const res = maybeEncode(data, encoding);
+    if (cb) cb(null, res);
+  }, (err: Error) => {
+    if (cb) {
+      (cb as (e: Error) => void)(denoErrorToNodeError(err, {
+        syscall: "readlink",
+        path,
+      }));
+    }
+  });
 }
 
 export const readlinkPromise = promisify(readlink) as (
@@ -88,5 +90,12 @@ export function readlinkSync(
 ): string | Uint8Array {
   path = path instanceof URL ? pathFromURL(path) : path;
 
-  return maybeEncode(Deno.readLinkSync(path), getEncoding(opt));
+  try {
+    return maybeEncode(Deno.readLinkSync(path), getEncoding(opt));
+  } catch (error) {
+    throw denoErrorToNodeError(error, {
+      syscall: "readlink",
+      path,
+    });
+  }
 }
diff --git a/ext/node/polyfills/_fs/_fs_stat.ts b/ext/node/polyfills/_fs/_fs_stat.ts
index c4ed82d577..d00c81ffb6 100644
--- a/ext/node/polyfills/_fs/_fs_stat.ts
+++ b/ext/node/polyfills/_fs/_fs_stat.ts
@@ -383,7 +383,10 @@ export function stat(
 
   Deno.stat(path).then(
     (stat) => callback(null, CFISBIS(stat, options.bigint)),
-    (err) => callback(denoErrorToNodeError(err, { syscall: "stat" })),
+    (err) =>
+      callback(
+        denoErrorToNodeError(err, { syscall: "stat", path: getPathname(path) }),
+      ),
   );
 }
 
@@ -417,9 +420,16 @@ export function statSync(
       return;
     }
     if (err instanceof Error) {
-      throw denoErrorToNodeError(err, { syscall: "stat" });
+      throw denoErrorToNodeError(err, {
+        syscall: "stat",
+        path: getPathname(path),
+      });
     } else {
       throw err;
     }
   }
 }
+
+function getPathname(path: string | URL) {
+  return typeof path === "string" ? path : path.pathname;
+}
diff --git a/ext/node/polyfills/_next_tick.ts b/ext/node/polyfills/_next_tick.ts
index 5ee27728d0..af306a29c8 100644
--- a/ext/node/polyfills/_next_tick.ts
+++ b/ext/node/polyfills/_next_tick.ts
@@ -62,6 +62,8 @@ export function processTicksAndRejections() {
               callback(...args);
           }
         }
+      } catch (e) {
+        reportError(e);
       } finally {
         // FIXME(bartlomieju): Deno currently doesn't support async hooks
         // if (destroyHooksExist())
@@ -87,8 +89,7 @@ export function runNextTicks() {
   //   runMicrotasks();
   // if (!hasTickScheduled() && !hasRejectionToWarn())
   //   return;
-  if (!core.hasTickScheduled()) {
-    core.runMicrotasks();
+  if (queue.isEmpty() || !core.hasTickScheduled()) {
     return true;
   }
 
diff --git a/ext/node/polyfills/_process/streams.mjs b/ext/node/polyfills/_process/streams.mjs
index 19c1c9c182..3573956c9d 100644
--- a/ext/node/polyfills/_process/streams.mjs
+++ b/ext/node/polyfills/_process/streams.mjs
@@ -63,13 +63,22 @@ export function createWritableStdioStream(writer, name, warmup = false) {
   stream.destroySoon = stream.destroy;
   stream._isStdio = true;
   stream.once("close", () => writer?.close());
+
+  // We cannot call `writer?.isTerminal()` eagerly here
+  let getIsTTY = () => writer?.isTerminal();
+  const getColumns = () =>
+    stream._columns ||
+    (writer?.isTerminal() ? Deno.consoleSize?.().columns : undefined);
+
   ObjectDefineProperties(stream, {
     columns: {
       __proto__: null,
       enumerable: true,
       configurable: true,
-      get: () =>
-        writer?.isTerminal() ? Deno.consoleSize?.().columns : undefined,
+      get: () => getColumns(),
+      set: (value) => {
+        stream._columns = value;
+      },
     },
     rows: {
       __proto__: null,
@@ -81,7 +90,11 @@ export function createWritableStdioStream(writer, name, warmup = false) {
       __proto__: null,
       enumerable: true,
       configurable: true,
-      get: () => writer?.isTerminal(),
+      // Allow users to overwrite it
+      get: () => getIsTTY(),
+      set: (value) => {
+        getIsTTY = () => value;
+      },
     },
     getWindowSize: {
       __proto__: null,
diff --git a/ext/node/polyfills/_tls_wrap.ts b/ext/node/polyfills/_tls_wrap.ts
index a614b45df0..e36fc637e7 100644
--- a/ext/node/polyfills/_tls_wrap.ts
+++ b/ext/node/polyfills/_tls_wrap.ts
@@ -68,6 +68,7 @@ export class TLSSocket extends net.Socket {
   secureConnecting: boolean;
   _SNICallback: any;
   servername: string | null;
+  alpnProtocol: string | boolean | null;
   alpnProtocols: string[] | null;
   authorized: boolean;
   authorizationError: any;
@@ -114,6 +115,7 @@ export class TLSSocket extends net.Socket {
     this.secureConnecting = true;
     this._SNICallback = null;
     this.servername = null;
+    this.alpnProtocol = null;
     this.alpnProtocols = tlsOptions.ALPNProtocols;
     this.authorized = false;
     this.authorizationError = null;
@@ -151,10 +153,21 @@ export class TLSSocket extends net.Socket {
       handle.afterConnect = async (req: any, status: number) => {
         try {
           const conn = await Deno.startTls(handle[kStreamBaseField], options);
+          try {
+            const hs = await conn.handshake();
+            if (hs.alpnProtocol) {
+              tlssock.alpnProtocol = hs.alpnProtocol;
+            } else {
+              tlssock.alpnProtocol = false;
+            }
+          } catch {
+            // Don't interrupt "secure" event to let the first read/write
+            // operation emit the error.
+          }
           handle[kStreamBaseField] = conn;
           tlssock.emit("secure");
           tlssock.removeListener("end", onConnectEnd);
-        } catch {
+        } catch (_) {
           // TODO(kt3k): Handle this
         }
         return afterConnect.call(handle, req, status);
@@ -269,6 +282,7 @@ export class ServerImpl extends EventEmitter {
         // Creates TCP handle and socket directly from Deno.TlsConn.
         // This works as TLS socket. We don't use TLSSocket class for doing
         // this because Deno.startTls only supports client side tcp connection.
+        // TODO(@satyarohith): set TLSSocket.alpnProtocol when we use TLSSocket class.
         const handle = new TCP(TCPConstants.SOCKET, await listener.accept());
         const socket = new net.Socket({ handle });
         this.emit("secureConnection", socket);
diff --git a/ext/node/polyfills/child_process.ts b/ext/node/polyfills/child_process.ts
index c37dfc410a..eda718ff34 100644
--- a/ext/node/polyfills/child_process.ts
+++ b/ext/node/polyfills/child_process.ts
@@ -132,6 +132,8 @@ export function fork(
           rm = 2;
         }
         execArgv.splice(index, rm);
+      } else if (flag.startsWith("--no-warnings")) {
+        execArgv[index] = "--quiet";
       } else {
         index++;
       }
diff --git a/ext/node/polyfills/http.ts b/ext/node/polyfills/http.ts
index f3f6f86ed8..9a920adeee 100644
--- a/ext/node/polyfills/http.ts
+++ b/ext/node/polyfills/http.ts
@@ -34,6 +34,7 @@ import {
   finished,
   Readable as NodeReadable,
   Writable as NodeWritable,
+  WritableOptions as NodeWritableOptions,
 } from "node:stream";
 import {
   kUniqueHeaders,
@@ -66,12 +67,13 @@ import { headersEntries } from "ext:deno_fetch/20_headers.js";
 import { timerId } from "ext:deno_web/03_abort_signal.js";
 import { clearTimeout as webClearTimeout } from "ext:deno_web/02_timers.js";
 import { resourceForReadableStream } from "ext:deno_web/06_streams.js";
-import { TcpConn } from "ext:deno_net/01_net.js";
+import { UpgradedConn } from "ext:deno_net/01_net.js";
 import { STATUS_CODES } from "node:_http_server";
 import { methods as METHODS } from "node:_http_common";
+import { deprecate } from "node:util";
 
 const { internalRidSymbol } = core;
-const { ArrayIsArray } = primordials;
+const { ArrayIsArray, StringPrototypeToLowerCase } = primordials;
 
 type Chunk = string | Buffer | Uint8Array;
 
@@ -516,7 +518,7 @@ class ClientRequest extends OutgoingMessage {
           );
           assert(typeof res.remoteAddrIp !== "undefined");
           assert(typeof res.remoteAddrIp !== "undefined");
-          const conn = new TcpConn(
+          const conn = new UpgradedConn(
             upgradeRid,
             {
               transport: "tcp",
@@ -1183,49 +1185,95 @@ function onError(self, error, cb) {
   }
 }
 
-export class ServerResponse extends NodeWritable {
-  statusCode = 200;
-  statusMessage?: string = undefined;
-  #headers: Record<string, string | string[]> = { __proto__: null };
-  #hasNonStringHeaders: boolean = false;
-  #readable: ReadableStream;
-  override writable = true;
-  // used by `npm:on-finished`
-  finished = false;
-  headersSent = false;
-  #resolve: (value: Response | PromiseLike<Response>) => void;
+export type ServerResponse = {
+  statusCode: number;
+  statusMessage?: string;
+
+  _headers: Record<string, string | string[]>;
+  _hasNonStringHeaders: boolean;
+
+  _readable: ReadableStream;
+  finished: boolean;
+  headersSent: boolean;
+  _resolve: (value: Response | PromiseLike<Response>) => void;
   // deno-lint-ignore no-explicit-any
-  #socketOverride: any | null = null;
+  _socketOverride: any | null;
+  // deno-lint-ignore no-explicit-any
+  socket: any | null;
 
-  static #enqueue(controller: ReadableStreamDefaultController, chunk: Chunk) {
-    try {
-      if (typeof chunk === "string") {
-        controller.enqueue(ENCODER.encode(chunk));
-      } else {
-        controller.enqueue(chunk);
-      }
-    } catch (_) {
-      // The stream might have been closed. Ignore the error.
-    }
-  }
+  setHeader(name: string, value: string | string[]): void;
+  appendHeader(name: string, value: string | string[]): void;
+  getHeader(name: string): string | string[];
+  removeHeader(name: string): void;
+  getHeaderNames(): string[];
+  getHeaders(): Record<string, string | number | string[]>;
+  hasHeader(name: string): boolean;
 
-  /** Returns true if the response body should be null with the given
-   * http status code */
-  static #bodyShouldBeNull(status: number) {
-    return status === 101 || status === 204 || status === 205 || status === 304;
-  }
+  writeHead(
+    status: number,
+    statusMessage?: string,
+    headers?:
+      | Record<string, string | number | string[]>
+      | Array<[string, string]>,
+  ): void;
+  writeHead(
+    status: number,
+    headers?:
+      | Record<string, string | number | string[]>
+      | Array<[string, string]>,
+  ): void;
 
-  constructor(
+  _ensureHeaders(singleChunk?: Chunk): void;
+
+  respond(final: boolean, singleChunk?: Chunk): void;
+  // deno-lint-ignore no-explicit-any
+  end(chunk?: any, encoding?: any, cb?: any): void;
+
+  flushHeaders(): void;
+  _implicitHeader(): void;
+
+  // Undocumented field used by `npm:light-my-request`.
+  _header: string;
+
+  assignSocket(socket): void;
+  detachSocket(socket): void;
+} & { -readonly [K in keyof NodeWritable]: NodeWritable[K] };
+
+type ServerResponseStatic = {
+  new (
     resolve: (value: Response | PromiseLike<Response>) => void,
     socket: FakeSocket,
-  ) {
-    let controller: ReadableByteStreamController;
-    const readable = new ReadableStream({
-      start(c) {
-        controller = c as ReadableByteStreamController;
-      },
-    });
-    super({
+  ): ServerResponse;
+  _enqueue(controller: ReadableStreamDefaultController, chunk: Chunk): void;
+  _bodyShouldBeNull(statusCode: number): boolean;
+};
+
+export const ServerResponse = function (
+  this: ServerResponse,
+  resolve: (value: Response | PromiseLike<Response>) => void,
+  socket: FakeSocket,
+) {
+  this.statusCode = 200;
+  this.statusMessage = undefined;
+  this._headers = { __proto__: null };
+  this._hasNonStringHeaders = false;
+  this.writable = true;
+
+  // used by `npm:on-finished`
+  this.finished = false;
+  this.headersSent = false;
+  this._socketOverride = null;
+
+  let controller: ReadableByteStreamController;
+  const readable = new ReadableStream({
+    start(c) {
+      controller = c as ReadableByteStreamController;
+    },
+  });
+
+  NodeWritable.call(
+    this,
+    {
       autoDestroy: true,
       defaultEncoding: "utf-8",
       emitClose: true,
@@ -1234,16 +1282,16 @@ export class ServerResponse extends NodeWritable {
       write: (chunk, encoding, cb) => {
         // Writes chunks are directly written to the socket if
         // one is assigned via assignSocket()
-        if (this.#socketOverride && this.#socketOverride.writable) {
-          this.#socketOverride.write(chunk, encoding);
+        if (this._socketOverride && this._socketOverride.writable) {
+          this._socketOverride.write(chunk, encoding);
           return cb();
         }
         if (!this.headersSent) {
-          ServerResponse.#enqueue(controller, chunk);
+          ServerResponse._enqueue(controller, chunk);
           this.respond(false);
           return cb();
         }
-        ServerResponse.#enqueue(controller, chunk);
+        ServerResponse._enqueue(controller, chunk);
         return cb();
       },
       final: (cb) => {
@@ -1259,192 +1307,269 @@ export class ServerResponse extends NodeWritable {
         }
         return cb(null);
       },
-    });
-    this.#readable = readable;
-    this.#resolve = resolve;
-    this.socket = socket;
-  }
+    } satisfies NodeWritableOptions,
+  );
 
-  setHeader(name: string, value: string | string[]) {
-    if (Array.isArray(value)) {
-      this.#hasNonStringHeaders = true;
-    }
-    this.#headers[name] = value;
-    return this;
-  }
+  this._readable = readable;
+  this._resolve = resolve;
+  this.socket = socket;
 
-  appendHeader(name: string, value: string | string[]) {
-    if (this.#headers[name] === undefined) {
-      if (Array.isArray(value)) this.#hasNonStringHeaders = true;
-      this.#headers[name] = value;
+  this._header = "";
+} as unknown as ServerResponseStatic;
+
+Object.setPrototypeOf(ServerResponse.prototype, NodeWritable.prototype);
+Object.setPrototypeOf(ServerResponse, NodeWritable);
+
+ServerResponse._enqueue = function (
+  this: ServerResponse,
+  controller: ReadableStreamDefaultController,
+  chunk: Chunk,
+) {
+  try {
+    if (typeof chunk === "string") {
+      controller.enqueue(ENCODER.encode(chunk));
     } else {
-      this.#hasNonStringHeaders = true;
-      if (!Array.isArray(this.#headers[name])) {
-        this.#headers[name] = [this.#headers[name]];
+      controller.enqueue(chunk);
+    }
+  } catch (_) {
+    // The stream might have been closed. Ignore the error.
+  }
+};
+
+/** Returns true if the response body should be null with the given
+ * http status code */
+ServerResponse._bodyShouldBeNull = function (
+  this: ServerResponse,
+  status: number,
+) {
+  return status === 101 || status === 204 || status === 205 || status === 304;
+};
+
+ServerResponse.prototype.setHeader = function (
+  this: ServerResponse,
+  name: string,
+  value: string | string[],
+) {
+  if (Array.isArray(value)) {
+    this._hasNonStringHeaders = true;
+  }
+  this._headers[StringPrototypeToLowerCase(name)] = value;
+  return this;
+};
+
+ServerResponse.prototype.appendHeader = function (
+  this: ServerResponse,
+  name: string,
+  value: string | string[],
+) {
+  const key = StringPrototypeToLowerCase(name);
+  if (this._headers[key] === undefined) {
+    if (Array.isArray(value)) this._hasNonStringHeaders = true;
+    this._headers[key] = value;
+  } else {
+    this._hasNonStringHeaders = true;
+    if (!Array.isArray(this._headers[key])) {
+      this._headers[key] = [this._headers[key]];
+    }
+    const header = this._headers[key];
+    if (Array.isArray(value)) {
+      header.push(...value);
+    } else {
+      header.push(value);
+    }
+  }
+  return this;
+};
+
+ServerResponse.prototype.getHeader = function (
+  this: ServerResponse,
+  name: string,
+) {
+  return this._headers[StringPrototypeToLowerCase(name)];
+};
+
+ServerResponse.prototype.removeHeader = function (
+  this: ServerResponse,
+  name: string,
+) {
+  delete this._headers[StringPrototypeToLowerCase(name)];
+};
+
+ServerResponse.prototype.getHeaderNames = function (this: ServerResponse) {
+  return Object.keys(this._headers);
+};
+
+ServerResponse.prototype.getHeaders = function (
+  this: ServerResponse,
+): Record<string, string | number | string[]> {
+  return { __proto__: null, ...this._headers };
+};
+
+ServerResponse.prototype.hasHeader = function (
+  this: ServerResponse,
+  name: string,
+) {
+  return Object.hasOwn(this._headers, name);
+};
+
+ServerResponse.prototype.writeHead = function (
+  this: ServerResponse,
+  status: number,
+  statusMessageOrHeaders?:
+    | string
+    | Record<string, string | number | string[]>
+    | Array<[string, string]>,
+  maybeHeaders?:
+    | Record<string, string | number | string[]>
+    | Array<[string, string]>,
+) {
+  this.statusCode = status;
+
+  let headers = null;
+  if (typeof statusMessageOrHeaders === "string") {
+    this.statusMessage = statusMessageOrHeaders;
+    if (maybeHeaders !== undefined) {
+      headers = maybeHeaders;
+    }
+  } else if (statusMessageOrHeaders !== undefined) {
+    headers = statusMessageOrHeaders;
+  }
+
+  if (headers !== null) {
+    if (ArrayIsArray(headers)) {
+      headers = headers as Array<[string, string]>;
+      for (let i = 0; i < headers.length; i++) {
+        this.appendHeader(headers[i][0], headers[i][1]);
       }
-      const header = this.#headers[name];
-      if (Array.isArray(value)) {
-        header.push(...value);
-      } else {
-        header.push(value);
+    } else {
+      headers = headers as Record<string, string>;
+      for (const k in headers) {
+        if (Object.hasOwn(headers, k)) {
+          this.setHeader(k, headers[k]);
+        }
       }
     }
-    return this;
   }
 
-  getHeader(name: string) {
-    return this.#headers[name];
-  }
-  removeHeader(name: string) {
-    delete this.#headers[name];
-  }
-  getHeaderNames() {
-    return Object.keys(this.#headers);
-  }
-  getHeaders(): Record<string, string | number | string[]> {
-    // @ts-ignore Ignore null __proto__
-    return { __proto__: null, ...this.#headers };
-  }
-  hasHeader(name: string) {
-    return Object.hasOwn(this.#headers, name);
-  }
+  return this;
+};
 
-  writeHead(
-    status: number,
-    statusMessage?: string,
-    headers?:
-      | Record<string, string | number | string[]>
-      | Array<[string, string]>,
-  ): this;
-  writeHead(
-    status: number,
-    headers?:
-      | Record<string, string | number | string[]>
-      | Array<[string, string]>,
-  ): this;
-  writeHead(
-    status: number,
-    statusMessageOrHeaders?:
-      | string
-      | Record<string, string | number | string[]>
-      | Array<[string, string]>,
-    maybeHeaders?:
-      | Record<string, string | number | string[]>
-      | Array<[string, string]>,
-  ): this {
-    this.statusCode = status;
+ServerResponse.prototype._ensureHeaders = function (
+  this: ServerResponse,
+  singleChunk?: Chunk,
+) {
+  if (this.statusCode === 200 && this.statusMessage === undefined) {
+    this.statusMessage = "OK";
+  }
+  if (typeof singleChunk === "string" && !this.hasHeader("content-type")) {
+    this.setHeader("content-type", "text/plain;charset=UTF-8");
+  }
+};
 
-    let headers = null;
-    if (typeof statusMessageOrHeaders === "string") {
-      this.statusMessage = statusMessageOrHeaders;
-      if (maybeHeaders !== undefined) {
-        headers = maybeHeaders;
-      }
-    } else if (statusMessageOrHeaders !== undefined) {
-      headers = statusMessageOrHeaders;
-    }
-
-    if (headers !== null) {
-      if (ArrayIsArray(headers)) {
-        headers = headers as Array<[string, string]>;
-        for (let i = 0; i < headers.length; i++) {
-          this.appendHeader(headers[i][0], headers[i][1]);
+ServerResponse.prototype.respond = function (
+  this: ServerResponse,
+  final: boolean,
+  singleChunk?: Chunk,
+) {
+  this.headersSent = true;
+  this._ensureHeaders(singleChunk);
+  let body = singleChunk ?? (final ? null : this._readable);
+  if (ServerResponse._bodyShouldBeNull(this.statusCode)) {
+    body = null;
+  }
+  let headers: Record<string, string> | [string, string][] = this
+    ._headers as Record<string, string>;
+  if (this._hasNonStringHeaders) {
+    headers = [];
+    // Guard is not needed as this is a null prototype object.
+    // deno-lint-ignore guard-for-in
+    for (const key in this._headers) {
+      const entry = this._headers[key];
+      if (Array.isArray(entry)) {
+        for (const value of entry) {
+          headers.push([key, value]);
         }
       } else {
-        headers = headers as Record<string, string>;
-        for (const k in headers) {
-          if (Object.hasOwn(headers, k)) {
-            this.setHeader(k, headers[k]);
-          }
-        }
+        headers.push([key, entry]);
       }
     }
-
-    return this;
-  }
-
-  #ensureHeaders(singleChunk?: Chunk) {
-    if (this.statusCode === 200 && this.statusMessage === undefined) {
-      this.statusMessage = "OK";
-    }
-    if (
-      typeof singleChunk === "string" &&
-      !this.hasHeader("content-type")
-    ) {
-      this.setHeader("content-type", "text/plain;charset=UTF-8");
-    }
-  }
-
-  respond(final: boolean, singleChunk?: Chunk) {
-    this.headersSent = true;
-    this.#ensureHeaders(singleChunk);
-    let body = singleChunk ?? (final ? null : this.#readable);
-    if (ServerResponse.#bodyShouldBeNull(this.statusCode)) {
-      body = null;
-    }
-    let headers: Record<string, string> | [string, string][] = this
-      .#headers as Record<string, string>;
-    if (this.#hasNonStringHeaders) {
-      headers = [];
-      // Guard is not needed as this is a null prototype object.
-      // deno-lint-ignore guard-for-in
-      for (const key in this.#headers) {
-        const entry = this.#headers[key];
-        if (Array.isArray(entry)) {
-          for (const value of entry) {
-            headers.push([key, value]);
-          }
-        } else {
-          headers.push([key, entry]);
-        }
-      }
-    }
-    this.#resolve(
-      new Response(body, {
-        headers,
-        status: this.statusCode,
-        statusText: this.statusMessage,
-      }),
-    );
   }
+  this._resolve(
+    new Response(body, {
+      headers,
+      status: this.statusCode,
+      statusText: this.statusMessage,
+    }),
+  );
+};
 
+ServerResponse.prototype.end = function (
+  this: ServerResponse,
   // deno-lint-ignore no-explicit-any
-  override end(chunk?: any, encoding?: any, cb?: any): this {
-    this.finished = true;
-    if (!chunk && "transfer-encoding" in this.#headers) {
-      // FIXME(bnoordhuis) Node sends a zero length chunked body instead, i.e.,
-      // the trailing "0\r\n", but respondWith() just hangs when I try that.
-      this.#headers["content-length"] = "0";
-      delete this.#headers["transfer-encoding"];
-    }
-
-    // @ts-expect-error The signature for cb is stricter than the one implemented here
-    return super.end(chunk, encoding, cb);
+  chunk?: any,
+  // deno-lint-ignore no-explicit-any
+  encoding?: any,
+  // deno-lint-ignore no-explicit-any
+  cb?: any,
+) {
+  this.finished = true;
+  if (!chunk && "transfer-encoding" in this._headers) {
+    // FIXME(bnoordhuis) Node sends a zero length chunked body instead, i.e.,
+    // the trailing "0\r\n", but respondWith() just hangs when I try that.
+    this._headers["content-length"] = "0";
+    delete this._headers["transfer-encoding"];
   }
 
-  flushHeaders() {
-    // no-op
-  }
+  // @ts-expect-error The signature for cb is stricter than the one implemented here
+  NodeWritable.prototype.end.call(this, chunk, encoding, cb);
+};
 
-  // Undocumented API used by `npm:compression`.
-  _implicitHeader() {
-    this.writeHead(this.statusCode);
-  }
+ServerResponse.prototype.flushHeaders = function (this: ServerResponse) {
+  // no-op
+};
 
-  assignSocket(socket) {
-    if (socket._httpMessage) {
-      throw new ERR_HTTP_SOCKET_ASSIGNED();
-    }
-    socket._httpMessage = this;
-    this.#socketOverride = socket;
-  }
+// Undocumented API used by `npm:compression`.
+ServerResponse.prototype._implicitHeader = function (this: ServerResponse) {
+  this.writeHead(this.statusCode);
+};
 
-  detachSocket(socket) {
-    assert(socket._httpMessage === this);
-    socket._httpMessage = null;
-    this.#socketOverride = null;
+ServerResponse.prototype.assignSocket = function (
+  this: ServerResponse,
+  socket,
+) {
+  if (socket._httpMessage) {
+    throw new ERR_HTTP_SOCKET_ASSIGNED();
   }
-}
+  socket._httpMessage = this;
+  this._socketOverride = socket;
+};
+
+ServerResponse.prototype.detachSocket = function (
+  this: ServerResponse,
+  socket,
+) {
+  assert(socket._httpMessage === this);
+  socket._httpMessage = null;
+  this._socketOverride = null;
+};
+
+Object.defineProperty(ServerResponse.prototype, "connection", {
+  get: deprecate(
+    function (this: ServerResponse) {
+      return this._socketOverride;
+    },
+    "ServerResponse.prototype.connection is deprecated",
+    "DEP0066",
+  ),
+  set: deprecate(
+    // deno-lint-ignore no-explicit-any
+    function (this: ServerResponse, socket: any) {
+      this._socketOverride = socket;
+    },
+    "ServerResponse.prototype.connection is deprecated",
+    "DEP0066",
+  ),
+});
 
 // TODO(@AaronO): optimize
 export class IncomingMessageForServer extends NodeReadable {
@@ -1677,6 +1802,8 @@ export class ServerImpl extends EventEmitter {
       this.#server.ref();
     }
     this.#unref = false;
+
+    return this;
   }
 
   unref() {
@@ -1684,6 +1811,8 @@ export class ServerImpl extends EventEmitter {
       this.#server.unref();
     }
     this.#unref = true;
+
+    return this;
   }
 
   close(cb?: (err?: Error) => void): this {
diff --git a/ext/node/polyfills/http2.ts b/ext/node/polyfills/http2.ts
index a9ced2bd9e..dc2379aebb 100644
--- a/ext/node/polyfills/http2.ts
+++ b/ext/node/polyfills/http2.ts
@@ -882,6 +882,7 @@ export class ClientHttp2Stream extends Duplex {
       trailersReady: false,
       endAfterHeaders: false,
       shutdownWritableCalled: false,
+      serverEndedCall: false,
     };
     this[kDenoResponse] = undefined;
     this[kDenoRid] = undefined;
@@ -1109,7 +1110,9 @@ export class ClientHttp2Stream extends Duplex {
       }
 
       debugHttp2(">>> chunk", chunk, finished, this[kDenoResponse].bodyRid);
-      if (chunk === null) {
+      if (finished || chunk === null) {
+        this[kState].serverEndedCall = true;
+
         const trailerList = await op_http2_client_get_response_trailers(
           this[kDenoResponse].bodyRid,
         );
@@ -1237,7 +1240,9 @@ export class ClientHttp2Stream extends Duplex {
     this[kSession] = undefined;
 
     session[kMaybeDestroy]();
-    callback(err);
+    if (callback) {
+      callback(err);
+    }
   }
 
   [kMaybeDestroy](code = constants.NGHTTP2_NO_ERROR) {
@@ -1280,6 +1285,9 @@ function shutdownWritable(stream, callback, streamRid) {
   if (state.flags & STREAM_FLAGS_HAS_TRAILERS) {
     onStreamTrailers(stream);
     callback();
+  } else if (state.serverEndedCall) {
+    debugHttp2(">>> stream finished");
+    callback();
   } else {
     op_http2_client_send_data(streamRid, new Uint8Array(), true)
       .then(() => {
diff --git a/ext/node/polyfills/internal/buffer.mjs b/ext/node/polyfills/internal/buffer.mjs
index 6687f73941..dd549221fa 100644
--- a/ext/node/polyfills/internal/buffer.mjs
+++ b/ext/node/polyfills/internal/buffer.mjs
@@ -2,10 +2,59 @@
 // Copyright Joyent and Node contributors. All rights reserved. MIT license.
 // Copyright Feross Aboukhadijeh, and other contributors. All rights reserved. MIT license.
 
-// TODO(petamoriken): enable prefer-primordials for node polyfills
-// deno-lint-ignore-file prefer-primordials
-
-import { core } from "ext:core/mod.js";
+import { core, primordials } from "ext:core/mod.js";
+const {
+  isAnyArrayBuffer,
+  isArrayBuffer,
+  isDataView,
+  isSharedArrayBuffer,
+  isTypedArray,
+} = core;
+const {
+  ArrayBufferPrototypeGetByteLength,
+  ArrayBufferPrototypeGetDetached,
+  ArrayIsArray,
+  ArrayPrototypeSlice,
+  BigInt,
+  DataViewPrototypeGetByteLength,
+  Float32Array,
+  Float64Array,
+  MathFloor,
+  MathMin,
+  Number,
+  NumberIsInteger,
+  NumberIsNaN,
+  NumberMAX_SAFE_INTEGER,
+  NumberMIN_SAFE_INTEGER,
+  NumberPrototypeToString,
+  ObjectCreate,
+  ObjectDefineProperty,
+  ObjectPrototypeIsPrototypeOf,
+  ObjectSetPrototypeOf,
+  RangeError,
+  SafeRegExp,
+  String,
+  StringFromCharCode,
+  StringPrototypeCharCodeAt,
+  StringPrototypeIncludes,
+  StringPrototypeReplace,
+  StringPrototypeToLowerCase,
+  StringPrototypeTrim,
+  SymbolFor,
+  SymbolToPrimitive,
+  TypeError,
+  TypeErrorPrototype,
+  TypedArrayPrototypeCopyWithin,
+  TypedArrayPrototypeFill,
+  TypedArrayPrototypeGetBuffer,
+  TypedArrayPrototypeGetByteLength,
+  TypedArrayPrototypeGetByteOffset,
+  TypedArrayPrototypeSet,
+  TypedArrayPrototypeSlice,
+  TypedArrayPrototypeSubarray,
+  Uint8Array,
+  Uint8ArrayPrototype,
+} = primordials;
 import { op_is_ascii, op_is_utf8, op_transcode } from "ext:core/ops";
 
 import { TextDecoder, TextEncoder } from "ext:deno_web/08_text_encoding.js";
@@ -24,11 +73,6 @@ import {
   hexToBytes,
   utf16leToBytes,
 } from "ext:deno_node/internal_binding/_utils.ts";
-import {
-  isAnyArrayBuffer,
-  isArrayBufferView,
-  isTypedArray,
-} from "ext:deno_node/internal/util/types.ts";
 import { normalizeEncoding } from "ext:deno_node/internal/util.mjs";
 import { validateBuffer } from "ext:deno_node/internal/validators.mjs";
 import { isUint8Array } from "ext:deno_node/internal/util/types.ts";
@@ -50,9 +94,13 @@ const utf8Encoder = new TextEncoder();
 
 // Temporary buffers to convert numbers.
 const float32Array = new Float32Array(1);
-const uInt8Float32Array = new Uint8Array(float32Array.buffer);
+const uInt8Float32Array = new Uint8Array(
+  TypedArrayPrototypeGetBuffer(float32Array),
+);
 const float64Array = new Float64Array(1);
-const uInt8Float64Array = new Uint8Array(float64Array.buffer);
+const uInt8Float64Array = new Uint8Array(
+  TypedArrayPrototypeGetBuffer(float64Array),
+);
 
 // Check endianness.
 float32Array[0] = -1; // 0xBF800000
@@ -64,10 +112,7 @@ export const kMaxLength = 2147483647;
 export const kStringMaxLength = 536870888;
 const MAX_UINT32 = 2 ** 32;
 
-const customInspectSymbol =
-  typeof Symbol === "function" && typeof Symbol["for"] === "function"
-    ? Symbol["for"]("nodejs.util.inspect.custom")
-    : null;
+const customInspectSymbol = SymbolFor("nodejs.util.inspect.custom");
 
 export const INSPECT_MAX_BYTES = 50;
 
@@ -76,23 +121,25 @@ export const constants = {
   MAX_STRING_LENGTH: kStringMaxLength,
 };
 
-Object.defineProperty(Buffer.prototype, "parent", {
+ObjectDefineProperty(Buffer.prototype, "parent", {
+  __proto__: null,
   enumerable: true,
   get: function () {
-    if (!Buffer.isBuffer(this)) {
+    if (!BufferIsBuffer(this)) {
       return void 0;
     }
-    return this.buffer;
+    return TypedArrayPrototypeGetBuffer(this);
   },
 });
 
-Object.defineProperty(Buffer.prototype, "offset", {
+ObjectDefineProperty(Buffer.prototype, "offset", {
+  __proto__: null,
   enumerable: true,
   get: function () {
-    if (!Buffer.isBuffer(this)) {
+    if (!BufferIsBuffer(this)) {
       return void 0;
     }
-    return this.byteOffset;
+    return TypedArrayPrototypeGetByteOffset(this);
   },
 });
 
@@ -103,10 +150,21 @@ function createBuffer(length) {
     );
   }
   const buf = new Uint8Array(length);
-  Object.setPrototypeOf(buf, Buffer.prototype);
+  ObjectSetPrototypeOf(buf, BufferPrototype);
   return buf;
 }
 
+/**
+ * @param {ArrayBufferLike} O
+ * @returns {boolean}
+ */
+function isDetachedBuffer(O) {
+  if (isSharedArrayBuffer(O)) {
+    return false;
+  }
+  return ArrayBufferPrototypeGetDetached(O);
+}
+
 export function Buffer(arg, encodingOrOffset, length) {
   if (typeof arg === "number") {
     if (typeof encodingOrOffset === "string") {
@@ -133,6 +191,7 @@ function _from(value, encodingOrOffset, length) {
       return fromArrayBuffer(value, encodingOrOffset, length);
     }
 
+    // deno-lint-ignore prefer-primordials
     const valueOf = value.valueOf && value.valueOf();
     if (
       valueOf != null &&
@@ -147,8 +206,8 @@ function _from(value, encodingOrOffset, length) {
       return b;
     }
 
-    if (typeof value[Symbol.toPrimitive] === "function") {
-      const primitive = value[Symbol.toPrimitive]("string");
+    if (typeof value[SymbolToPrimitive] === "function") {
+      const primitive = value[SymbolToPrimitive]("string");
       if (typeof primitive === "string") {
         return fromString(primitive, encodingOrOffset);
       }
@@ -162,13 +221,19 @@ function _from(value, encodingOrOffset, length) {
   );
 }
 
-Buffer.from = function from(value, encodingOrOffset, length) {
+const BufferFrom = Buffer.from = function from(
+  value,
+  encodingOrOffset,
+  length,
+) {
   return _from(value, encodingOrOffset, length);
 };
 
-Object.setPrototypeOf(Buffer.prototype, Uint8Array.prototype);
+const BufferPrototype = Buffer.prototype;
 
-Object.setPrototypeOf(Buffer, Uint8Array);
+ObjectSetPrototypeOf(Buffer.prototype, Uint8ArrayPrototype);
+
+ObjectSetPrototypeOf(Buffer, Uint8Array);
 
 function assertSize(size) {
   validateNumber(size, "size", 0, kMaxLength);
@@ -186,6 +251,7 @@ function _alloc(size, fill, encoding) {
         encoding,
       );
     }
+    // deno-lint-ignore prefer-primordials
     return buffer.fill(fill, encoding);
   }
   return buffer;
@@ -212,13 +278,14 @@ function fromString(string, encoding) {
   if (typeof encoding !== "string" || encoding === "") {
     encoding = "utf8";
   }
-  if (!Buffer.isEncoding(encoding)) {
+  if (!BufferIsEncoding(encoding)) {
     throw new codes.ERR_UNKNOWN_ENCODING(encoding);
   }
   const length = byteLength(string, encoding) | 0;
   let buf = createBuffer(length);
   const actual = buf.write(string, encoding);
   if (actual !== length) {
+    // deno-lint-ignore prefer-primordials
     buf = buf.slice(0, actual);
   }
   return buf;
@@ -226,11 +293,12 @@ function fromString(string, encoding) {
 
 function fromArrayLike(obj) {
   const buf = new Uint8Array(obj);
-  Object.setPrototypeOf(buf, Buffer.prototype);
+  ObjectSetPrototypeOf(buf, BufferPrototype);
   return buf;
 }
 
 function fromObject(obj) {
+  // deno-lint-ignore prefer-primordials
   if (obj.length !== undefined || isAnyArrayBuffer(obj.buffer)) {
     if (typeof obj.length !== "number") {
       return createBuffer(0);
@@ -239,7 +307,7 @@ function fromObject(obj) {
     return fromArrayLike(obj);
   }
 
-  if (obj.type === "Buffer" && Array.isArray(obj.data)) {
+  if (obj.type === "Buffer" && ArrayIsArray(obj.data)) {
     return fromArrayLike(obj.data);
   }
 }
@@ -248,7 +316,7 @@ function checked(length) {
   if (length >= kMaxLength) {
     throw new RangeError(
       "Attempt to allocate Buffer larger than maximum size: 0x" +
-        kMaxLength.toString(16) + " bytes",
+        NumberPrototypeToString(kMaxLength, 16) + " bytes",
     );
   }
   return length | 0;
@@ -256,25 +324,33 @@ function checked(length) {
 
 export function SlowBuffer(length) {
   assertSize(length);
-  return Buffer.alloc(+length);
+  return _alloc(+length);
 }
 
-Object.setPrototypeOf(SlowBuffer.prototype, Uint8Array.prototype);
+ObjectSetPrototypeOf(SlowBuffer.prototype, Uint8ArrayPrototype);
 
-Object.setPrototypeOf(SlowBuffer, Uint8Array);
+ObjectSetPrototypeOf(SlowBuffer, Uint8Array);
 
-Buffer.isBuffer = function isBuffer(b) {
-  return b != null && b._isBuffer === true && b !== Buffer.prototype;
+const BufferIsBuffer = Buffer.isBuffer = function isBuffer(b) {
+  return b != null && b._isBuffer === true && b !== BufferPrototype;
 };
 
-Buffer.compare = function compare(a, b) {
-  if (isInstance(a, Uint8Array)) {
-    a = Buffer.from(a, a.offset, a.byteLength);
+const BufferCompare = Buffer.compare = function compare(a, b) {
+  if (isUint8Array(a)) {
+    a = BufferFrom(
+      a,
+      TypedArrayPrototypeGetByteOffset(a),
+      TypedArrayPrototypeGetByteLength(a),
+    );
   }
-  if (isInstance(b, Uint8Array)) {
-    b = Buffer.from(b, b.offset, b.byteLength);
+  if (isUint8Array(b)) {
+    b = BufferFrom(
+      b,
+      TypedArrayPrototypeGetByteOffset(b),
+      TypedArrayPrototypeGetByteLength(b),
+    );
   }
-  if (!Buffer.isBuffer(a) || !Buffer.isBuffer(b)) {
+  if (!BufferIsBuffer(a) || !BufferIsBuffer(b)) {
     throw new TypeError(
       'The "buf1", "buf2" arguments must be one of type Buffer or Uint8Array',
     );
@@ -284,7 +360,7 @@ Buffer.compare = function compare(a, b) {
   }
   let x = a.length;
   let y = b.length;
-  for (let i = 0, len = Math.min(x, y); i < len; ++i) {
+  for (let i = 0, len = MathMin(x, y); i < len; ++i) {
     if (a[i] !== b[i]) {
       x = a[i];
       y = b[i];
@@ -300,18 +376,18 @@ Buffer.compare = function compare(a, b) {
   return 0;
 };
 
-Buffer.isEncoding = function isEncoding(encoding) {
+const BufferIsEncoding = Buffer.isEncoding = function isEncoding(encoding) {
   return typeof encoding === "string" && encoding.length !== 0 &&
     normalizeEncoding(encoding) !== undefined;
 };
 
 Buffer.concat = function concat(list, length) {
-  if (!Array.isArray(list)) {
+  if (!ArrayIsArray(list)) {
     throw new codes.ERR_INVALID_ARG_TYPE("list", "Array", list);
   }
 
   if (list.length === 0) {
-    return Buffer.alloc(0);
+    return _alloc(0);
   }
 
   if (length === undefined) {
@@ -325,7 +401,7 @@ Buffer.concat = function concat(list, length) {
     validateOffset(length, "length");
   }
 
-  const buffer = Buffer.allocUnsafe(length);
+  const buffer = _allocUnsafe(length);
   let pos = 0;
   for (let i = 0; i < list.length; i++) {
     const buf = list[i];
@@ -346,7 +422,7 @@ Buffer.concat = function concat(list, length) {
     // Zero-fill the remaining bytes if the specified `length` was more than
     // the actual total length, i.e. if we have some remaining allocated bytes
     // there were not initialized.
-    buffer.fill(0, pos, length);
+    TypedArrayPrototypeFill(buffer, 0, pos, length);
   }
 
   return buffer;
@@ -354,7 +430,18 @@ Buffer.concat = function concat(list, length) {
 
 function byteLength(string, encoding) {
   if (typeof string !== "string") {
-    if (isArrayBufferView(string) || isAnyArrayBuffer(string)) {
+    if (isTypedArray(string)) {
+      return TypedArrayPrototypeGetByteLength(string);
+    }
+    if (isDataView(string)) {
+      return DataViewPrototypeGetByteLength(string);
+    }
+    if (isArrayBuffer(string)) {
+      return ArrayBufferPrototypeGetByteLength(string);
+    }
+    if (isSharedArrayBuffer(string)) {
+      // TODO(petamoriken): add SharedArayBuffer to primordials
+      // deno-lint-ignore prefer-primordials
       return string.byteLength;
     }
 
@@ -463,6 +550,7 @@ Buffer.prototype.toString = function toString(encoding, start, end) {
     throw new codes.ERR_UNKNOWN_ENCODING(encoding);
   }
 
+  // deno-lint-ignore prefer-primordials
   return ops.slice(this, start, end);
 };
 
@@ -479,22 +567,29 @@ Buffer.prototype.equals = function equals(b) {
   if (this === b) {
     return true;
   }
-  return Buffer.compare(this, b) === 0;
+  return BufferCompare(this, b) === 0;
 };
 
-Buffer.prototype.inspect = function inspect() {
-  let str = "";
-  const max = INSPECT_MAX_BYTES;
-  str = this.toString("hex", 0, max).replace(/(.{2})/g, "$1 ").trim();
-  if (this.length > max) {
-    str += " ... ";
-  }
-  return "<Buffer " + str + ">";
-};
+const SPACER_PATTERN = new SafeRegExp(/(.{2})/g);
 
-if (customInspectSymbol) {
-  Buffer.prototype[customInspectSymbol] = Buffer.prototype.inspect;
-}
+Buffer.prototype[customInspectSymbol] =
+  Buffer.prototype.inspect =
+    function inspect() {
+      let str = "";
+      const max = INSPECT_MAX_BYTES;
+      str = StringPrototypeTrim(
+        StringPrototypeReplace(
+          // deno-lint-ignore prefer-primordials
+          this.toString("hex", 0, max),
+          SPACER_PATTERN,
+          "$1 ",
+        ),
+      );
+      if (this.length > max) {
+        str += " ... ";
+      }
+      return "<Buffer " + str + ">";
+    };
 
 Buffer.prototype.compare = function compare(
   target,
@@ -503,10 +598,14 @@ Buffer.prototype.compare = function compare(
   thisStart,
   thisEnd,
 ) {
-  if (isInstance(target, Uint8Array)) {
-    target = Buffer.from(target, target.offset, target.byteLength);
+  if (isUint8Array(target)) {
+    target = BufferFrom(
+      target,
+      TypedArrayPrototypeGetByteOffset(target),
+      TypedArrayPrototypeGetByteLength(target),
+    );
   }
-  if (!Buffer.isBuffer(target)) {
+  if (!BufferIsBuffer(target)) {
     throw new codes.ERR_INVALID_ARG_TYPE(
       "target",
       ["Buffer", "Uint8Array"],
@@ -563,8 +662,9 @@ Buffer.prototype.compare = function compare(
   }
   let x = thisEnd - thisStart;
   let y = end - start;
-  const len = Math.min(x, y);
-  const thisCopy = this.slice(thisStart, thisEnd);
+  const len = MathMin(x, y);
+  const thisCopy = TypedArrayPrototypeSlice(this, thisStart, thisEnd);
+  // deno-lint-ignore prefer-primordials
   const targetCopy = target.slice(start, end);
   for (let i = 0; i < len; ++i) {
     if (thisCopy[i] !== targetCopy[i]) {
@@ -594,7 +694,8 @@ function bidirectionalIndexOf(buffer, val, byteOffset, encoding, dir) {
     byteOffset = -0x80000000;
   }
   byteOffset = +byteOffset;
-  if (Number.isNaN(byteOffset)) {
+  if (NumberIsNaN(byteOffset)) {
+    // deno-lint-ignore prefer-primordials
     byteOffset = dir ? 0 : (buffer.length || buffer.byteLength);
   }
   dir = !!dir;
@@ -614,6 +715,7 @@ function bidirectionalIndexOf(buffer, val, byteOffset, encoding, dir) {
     if (ops === undefined) {
       throw new codes.ERR_UNKNOWN_ENCODING(encoding);
     }
+    // deno-lint-ignore prefer-primordials
     return ops.indexOf(buffer, val, byteOffset, dir);
   }
 
@@ -630,6 +732,7 @@ function bidirectionalIndexOf(buffer, val, byteOffset, encoding, dir) {
 }
 
 Buffer.prototype.includes = function includes(val, byteOffset, encoding) {
+  // deno-lint-ignore prefer-primordials
   return this.indexOf(val, byteOffset, encoding) !== -1;
 };
 
@@ -649,7 +752,7 @@ Buffer.prototype.asciiSlice = function asciiSlice(offset, length) {
   if (offset === 0 && length === this.length) {
     return bytesToAscii(this);
   } else {
-    return bytesToAscii(this.slice(offset, length));
+    return bytesToAscii(TypedArrayPrototypeSlice(this, offset, length));
   }
 };
 
@@ -664,7 +767,9 @@ Buffer.prototype.base64Slice = function base64Slice(
   if (offset === 0 && length === this.length) {
     return forgivingBase64Encode(this);
   } else {
-    return forgivingBase64Encode(this.slice(offset, length));
+    return forgivingBase64Encode(
+      TypedArrayPrototypeSlice(this, offset, length),
+    );
   }
 };
 
@@ -683,7 +788,9 @@ Buffer.prototype.base64urlSlice = function base64urlSlice(
   if (offset === 0 && length === this.length) {
     return forgivingBase64UrlEncode(this);
   } else {
-    return forgivingBase64UrlEncode(this.slice(offset, length));
+    return forgivingBase64UrlEncode(
+      TypedArrayPrototypeSlice(this, offset, length),
+    );
   }
 };
 
@@ -728,7 +835,7 @@ Buffer.prototype.ucs2Slice = function ucs2Slice(offset, length) {
   if (offset === 0 && length === this.length) {
     return bytesToUtf16le(this);
   } else {
-    return bytesToUtf16le(this.slice(offset, length));
+    return bytesToUtf16le(TypedArrayPrototypeSlice(this, offset, length));
   }
 };
 
@@ -747,9 +854,9 @@ Buffer.prototype.utf8Slice = function utf8Slice(string, offset, length) {
 
 Buffer.prototype.utf8Write = function utf8Write(string, offset, length) {
   offset = offset || 0;
-  const maxLength = Math.min(length || Infinity, this.length - offset);
+  const maxLength = MathMin(length || Infinity, this.length - offset);
   const buf = offset || maxLength < this.length
-    ? this.subarray(offset, maxLength + offset)
+    ? TypedArrayPrototypeSubarray(this, offset, maxLength + offset)
     : this;
   return utf8Encoder.encodeInto(string, buf).written;
 };
@@ -801,7 +908,7 @@ Buffer.prototype.write = function write(string, offset, length, encoding) {
 Buffer.prototype.toJSON = function toJSON() {
   return {
     type: "Buffer",
-    data: Array.prototype.slice.call(this._arr || this, 0),
+    data: ArrayPrototypeSlice(this._arr || this, 0),
   };
 };
 function fromArrayBuffer(obj, byteOffset, length) {
@@ -810,11 +917,12 @@ function fromArrayBuffer(obj, byteOffset, length) {
     byteOffset = 0;
   } else {
     byteOffset = +byteOffset;
-    if (Number.isNaN(byteOffset)) {
+    if (NumberIsNaN(byteOffset)) {
       byteOffset = 0;
     }
   }
 
+  // deno-lint-ignore prefer-primordials
   const maxLength = obj.byteLength - byteOffset;
 
   if (maxLength < 0) {
@@ -836,7 +944,7 @@ function fromArrayBuffer(obj, byteOffset, length) {
   }
 
   const buffer = new Uint8Array(obj, byteOffset, length);
-  Object.setPrototypeOf(buffer, Buffer.prototype);
+  ObjectSetPrototypeOf(buffer, BufferPrototype);
   return buffer;
 }
 
@@ -844,6 +952,7 @@ function _base64Slice(buf, start, end) {
   if (start === 0 && end === buf.length) {
     return forgivingBase64Encode(buf);
   } else {
+    // deno-lint-ignore prefer-primordials
     return forgivingBase64Encode(buf.slice(start, end));
   }
 }
@@ -852,9 +961,10 @@ const decoder = new TextDecoder();
 
 function _utf8Slice(buf, start, end) {
   try {
+    // deno-lint-ignore prefer-primordials
     return decoder.decode(buf.slice(start, end));
   } catch (err) {
-    if (err instanceof TypeError) {
+    if (ObjectPrototypeIsPrototypeOf(TypeErrorPrototype, err)) {
       throw new NodeError("ERR_STRING_TOO_LONG", "String too long");
     }
     throw err;
@@ -863,9 +973,9 @@ function _utf8Slice(buf, start, end) {
 
 function _latin1Slice(buf, start, end) {
   let ret = "";
-  end = Math.min(buf.length, end);
+  end = MathMin(buf.length, end);
   for (let i = start; i < end; ++i) {
-    ret += String.fromCharCode(buf[i]);
+    ret += StringFromCharCode(buf[i]);
   }
   return ret;
 }
@@ -994,42 +1104,38 @@ Buffer.prototype.readUint32BE = Buffer.prototype.readUInt32BE = readUInt32BE;
 
 Buffer.prototype.readBigUint64LE =
   Buffer.prototype.readBigUInt64LE =
-    defineBigIntMethod(
-      function readBigUInt64LE(offset) {
-        offset = offset >>> 0;
-        validateNumber(offset, "offset");
-        const first = this[offset];
-        const last = this[offset + 7];
-        if (first === void 0 || last === void 0) {
-          boundsError(offset, this.length - 8);
-        }
-        const lo = first + this[++offset] * 2 ** 8 +
-          this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 24;
-        const hi = this[++offset] + this[++offset] * 2 ** 8 +
-          this[++offset] * 2 ** 16 + last * 2 ** 24;
-        return BigInt(lo) + (BigInt(hi) << BigInt(32));
-      },
-    );
+    function readBigUInt64LE(offset) {
+      offset = offset >>> 0;
+      validateNumber(offset, "offset");
+      const first = this[offset];
+      const last = this[offset + 7];
+      if (first === void 0 || last === void 0) {
+        boundsError(offset, this.length - 8);
+      }
+      const lo = first + this[++offset] * 2 ** 8 +
+        this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 24;
+      const hi = this[++offset] + this[++offset] * 2 ** 8 +
+        this[++offset] * 2 ** 16 + last * 2 ** 24;
+      return BigInt(lo) + (BigInt(hi) << 32n);
+    };
 
 Buffer.prototype.readBigUint64BE =
   Buffer.prototype.readBigUInt64BE =
-    defineBigIntMethod(
-      function readBigUInt64BE(offset) {
-        offset = offset >>> 0;
-        validateNumber(offset, "offset");
-        const first = this[offset];
-        const last = this[offset + 7];
-        if (first === void 0 || last === void 0) {
-          boundsError(offset, this.length - 8);
-        }
-        const hi = first * 2 ** 24 + this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 8 + this[++offset];
-        const lo = this[++offset] * 2 ** 24 + this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 8 + last;
-        return (BigInt(hi) << BigInt(32)) + BigInt(lo);
-      },
-    );
+    function readBigUInt64BE(offset) {
+      offset = offset >>> 0;
+      validateNumber(offset, "offset");
+      const first = this[offset];
+      const last = this[offset + 7];
+      if (first === void 0 || last === void 0) {
+        boundsError(offset, this.length - 8);
+      }
+      const hi = first * 2 ** 24 + this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 8 + this[++offset];
+      const lo = this[++offset] * 2 ** 24 + this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 8 + last;
+      return (BigInt(hi) << 32n) + BigInt(lo);
+    };
 
 Buffer.prototype.readIntLE = function readIntLE(
   offset,
@@ -1148,43 +1254,39 @@ Buffer.prototype.readInt32BE = function readInt32BE(offset = 0) {
     last;
 };
 
-Buffer.prototype.readBigInt64LE = defineBigIntMethod(
-  function readBigInt64LE(offset) {
-    offset = offset >>> 0;
-    validateNumber(offset, "offset");
-    const first = this[offset];
-    const last = this[offset + 7];
-    if (first === void 0 || last === void 0) {
-      boundsError(offset, this.length - 8);
-    }
-    const val = this[offset + 4] + this[offset + 5] * 2 ** 8 +
-      this[offset + 6] * 2 ** 16 + (last << 24);
-    return (BigInt(val) << BigInt(32)) +
-      BigInt(
-        first + this[++offset] * 2 ** 8 + this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 24,
-      );
-  },
-);
+Buffer.prototype.readBigInt64LE = function readBigInt64LE(offset) {
+  offset = offset >>> 0;
+  validateNumber(offset, "offset");
+  const first = this[offset];
+  const last = this[offset + 7];
+  if (first === void 0 || last === void 0) {
+    boundsError(offset, this.length - 8);
+  }
+  const val = this[offset + 4] + this[offset + 5] * 2 ** 8 +
+    this[offset + 6] * 2 ** 16 + (last << 24);
+  return (BigInt(val) << 32n) +
+    BigInt(
+      first + this[++offset] * 2 ** 8 + this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 24,
+    );
+};
 
-Buffer.prototype.readBigInt64BE = defineBigIntMethod(
-  function readBigInt64BE(offset) {
-    offset = offset >>> 0;
-    validateNumber(offset, "offset");
-    const first = this[offset];
-    const last = this[offset + 7];
-    if (first === void 0 || last === void 0) {
-      boundsError(offset, this.length - 8);
-    }
-    const val = (first << 24) + this[++offset] * 2 ** 16 +
-      this[++offset] * 2 ** 8 + this[++offset];
-    return (BigInt(val) << BigInt(32)) +
-      BigInt(
-        this[++offset] * 2 ** 24 + this[++offset] * 2 ** 16 +
-          this[++offset] * 2 ** 8 + last,
-      );
-  },
-);
+Buffer.prototype.readBigInt64BE = function readBigInt64BE(offset) {
+  offset = offset >>> 0;
+  validateNumber(offset, "offset");
+  const first = this[offset];
+  const last = this[offset + 7];
+  if (first === void 0 || last === void 0) {
+    boundsError(offset, this.length - 8);
+  }
+  const val = (first << 24) + this[++offset] * 2 ** 16 +
+    this[++offset] * 2 ** 8 + this[++offset];
+  return (BigInt(val) << 32n) +
+    BigInt(
+      this[++offset] * 2 ** 24 + this[++offset] * 2 ** 16 +
+        this[++offset] * 2 ** 8 + last,
+    );
+};
 
 Buffer.prototype.readFloatLE = function readFloatLE(offset) {
   return bigEndian
@@ -1293,7 +1395,7 @@ Buffer.prototype.writeUint32BE =
 
 function wrtBigUInt64LE(buf, value, offset, min, max) {
   checkIntBI(value, min, max, buf, offset, 7);
-  let lo = Number(value & BigInt(4294967295));
+  let lo = Number(value & 4294967295n);
   buf[offset++] = lo;
   lo = lo >> 8;
   buf[offset++] = lo;
@@ -1301,7 +1403,7 @@ function wrtBigUInt64LE(buf, value, offset, min, max) {
   buf[offset++] = lo;
   lo = lo >> 8;
   buf[offset++] = lo;
-  let hi = Number(value >> BigInt(32) & BigInt(4294967295));
+  let hi = Number(value >> 32n & 4294967295n);
   buf[offset++] = hi;
   hi = hi >> 8;
   buf[offset++] = hi;
@@ -1314,7 +1416,7 @@ function wrtBigUInt64LE(buf, value, offset, min, max) {
 
 function wrtBigUInt64BE(buf, value, offset, min, max) {
   checkIntBI(value, min, max, buf, offset, 7);
-  let lo = Number(value & BigInt(4294967295));
+  let lo = Number(value & 4294967295n);
   buf[offset + 7] = lo;
   lo = lo >> 8;
   buf[offset + 6] = lo;
@@ -1322,7 +1424,7 @@ function wrtBigUInt64BE(buf, value, offset, min, max) {
   buf[offset + 5] = lo;
   lo = lo >> 8;
   buf[offset + 4] = lo;
-  let hi = Number(value >> BigInt(32) & BigInt(4294967295));
+  let hi = Number(value >> 32n & 4294967295n);
   buf[offset + 3] = hi;
   hi = hi >> 8;
   buf[offset + 2] = hi;
@@ -1335,31 +1437,27 @@ function wrtBigUInt64BE(buf, value, offset, min, max) {
 
 Buffer.prototype.writeBigUint64LE =
   Buffer.prototype.writeBigUInt64LE =
-    defineBigIntMethod(
-      function writeBigUInt64LE(value, offset = 0) {
-        return wrtBigUInt64LE(
-          this,
-          value,
-          offset,
-          BigInt(0),
-          BigInt("0xffffffffffffffff"),
-        );
-      },
-    );
+    function writeBigUInt64LE(value, offset = 0) {
+      return wrtBigUInt64LE(
+        this,
+        value,
+        offset,
+        0n,
+        0xffffffffffffffffn,
+      );
+    };
 
 Buffer.prototype.writeBigUint64BE =
   Buffer.prototype.writeBigUInt64BE =
-    defineBigIntMethod(
-      function writeBigUInt64BE(value, offset = 0) {
-        return wrtBigUInt64BE(
-          this,
-          value,
-          offset,
-          BigInt(0),
-          BigInt("0xffffffffffffffff"),
-        );
-      },
-    );
+    function writeBigUInt64BE(value, offset = 0) {
+      return wrtBigUInt64BE(
+        this,
+        value,
+        offset,
+        0n,
+        0xffffffffffffffffn,
+      );
+    };
 
 Buffer.prototype.writeIntLE = function writeIntLE(
   value,
@@ -1450,29 +1548,25 @@ Buffer.prototype.writeInt32BE = function writeInt32BE(value, offset = 0) {
   return writeU_Int32BE(this, value, offset, -0x80000000, 0x7fffffff);
 };
 
-Buffer.prototype.writeBigInt64LE = defineBigIntMethod(
-  function writeBigInt64LE(value, offset = 0) {
-    return wrtBigUInt64LE(
-      this,
-      value,
-      offset,
-      -BigInt("0x8000000000000000"),
-      BigInt("0x7fffffffffffffff"),
-    );
-  },
-);
+Buffer.prototype.writeBigInt64LE = function writeBigInt64LE(value, offset = 0) {
+  return wrtBigUInt64LE(
+    this,
+    value,
+    offset,
+    -0x8000000000000000n,
+    0x7fffffffffffffffn,
+  );
+};
 
-Buffer.prototype.writeBigInt64BE = defineBigIntMethod(
-  function writeBigInt64BE(value, offset = 0) {
-    return wrtBigUInt64BE(
-      this,
-      value,
-      offset,
-      -BigInt("0x8000000000000000"),
-      BigInt("0x7fffffffffffffff"),
-    );
-  },
-);
+Buffer.prototype.writeBigInt64BE = function writeBigInt64BE(value, offset = 0) {
+  return wrtBigUInt64BE(
+    this,
+    value,
+    offset,
+    -0x8000000000000000n,
+    0x7fffffffffffffffn,
+  );
+};
 
 Buffer.prototype.writeFloatLE = function writeFloatLE(
   value,
@@ -1600,14 +1694,12 @@ Buffer.prototype.copy = function copy(
   }
 
   const len = sourceEnd - sourceStart;
-  if (
-    this === target && typeof Uint8Array.prototype.copyWithin === "function"
-  ) {
-    this.copyWithin(targetStart, sourceStart, sourceEnd);
+  if (this === target) {
+    TypedArrayPrototypeCopyWithin(this, targetStart, sourceStart, sourceEnd);
   } else {
-    Uint8Array.prototype.set.call(
+    TypedArrayPrototypeSet(
       target,
-      this.subarray(sourceStart, sourceEnd),
+      TypedArrayPrototypeSubarray(this, sourceStart, sourceEnd),
       targetStart,
     );
   }
@@ -1627,11 +1719,11 @@ Buffer.prototype.fill = function fill(val, start, end, encoding) {
     if (encoding !== void 0 && typeof encoding !== "string") {
       throw new TypeError("encoding must be a string");
     }
-    if (typeof encoding === "string" && !Buffer.isEncoding(encoding)) {
+    if (typeof encoding === "string" && !BufferIsEncoding(encoding)) {
       throw new TypeError("Unknown encoding: " + encoding);
     }
     if (val.length === 1) {
-      const code = val.charCodeAt(0);
+      const code = StringPrototypeCharCodeAt(val, 0);
       if (encoding === "utf8" && code < 128 || encoding === "latin1") {
         val = code;
       }
@@ -1658,7 +1750,7 @@ Buffer.prototype.fill = function fill(val, start, end, encoding) {
       this[i] = val;
     }
   } else {
-    const bytes = Buffer.isBuffer(val) ? val : Buffer.from(val, encoding);
+    const bytes = BufferIsBuffer(val) ? val : BufferFrom(val, encoding);
     const len = bytes.length;
     if (len === 0) {
       throw new codes.ERR_INVALID_ARG_VALUE(
@@ -1685,7 +1777,7 @@ function checkIntBI(value, min, max, buf, offset, byteLength2) {
     const n = typeof min === "bigint" ? "n" : "";
     let range;
     if (byteLength2 > 3) {
-      if (min === 0 || min === BigInt(0)) {
+      if (min === 0 || min === 0n) {
         range = `>= 0${n} and < 2${n} ** ${(byteLength2 + 1) * 8}${n}`;
       } else {
         range = `>= -(2${n} ** ${(byteLength2 + 1) * 8 - 1}${n}) and < 2 ** ${
@@ -1710,7 +1802,7 @@ function checkIntBI(value, min, max, buf, offset, byteLength2) {
 function blitBuffer(src, dst, offset, byteLength = Infinity) {
   const srcLength = src.length;
   // Establish the number of bytes to be written
-  const bytesToWrite = Math.min(
+  const bytesToWrite = MathMin(
     // If byte length is defined in the call, then it sets an upper bound,
     // otherwise it is Infinity and is never chosen.
     byteLength,
@@ -1730,15 +1822,9 @@ function blitBuffer(src, dst, offset, byteLength = Infinity) {
   return bytesToWrite;
 }
 
-function isInstance(obj, type) {
-  return obj instanceof type ||
-    obj != null && obj.constructor != null &&
-      obj.constructor.name != null && obj.constructor.name === type.name;
-}
-
 const hexSliceLookupTable = function () {
   const alphabet = "0123456789abcdef";
-  const table = new Array(256);
+  const table = [];
   for (let i = 0; i < 16; ++i) {
     const i16 = i * 16;
     for (let j = 0; j < 16; ++j) {
@@ -1748,14 +1834,6 @@ const hexSliceLookupTable = function () {
   return table;
 }();
 
-function defineBigIntMethod(fn) {
-  return typeof BigInt === "undefined" ? BufferBigIntNotDefined : fn;
-}
-
-function BufferBigIntNotDefined() {
-  throw new Error("BigInt not supported");
-}
-
 export function readUInt48LE(buf, offset = 0) {
   validateNumber(offset, "offset");
   const first = buf[offset];
@@ -2079,10 +2157,10 @@ export function byteLengthUtf8(str) {
 
 function base64ByteLength(str, bytes) {
   // Handle padding
-  if (str.charCodeAt(bytes - 1) === 0x3D) {
+  if (StringPrototypeCharCodeAt(str, bytes - 1) === 0x3D) {
     bytes--;
   }
-  if (bytes > 1 && str.charCodeAt(bytes - 1) === 0x3D) {
+  if (bytes > 1 && StringPrototypeCharCodeAt(str, bytes - 1) === 0x3D) {
     bytes--;
   }
 
@@ -2090,7 +2168,7 @@ function base64ByteLength(str, bytes) {
   return (bytes * 3) >>> 2;
 }
 
-export const encodingsMap = Object.create(null);
+export const encodingsMap = ObjectCreate(null);
 for (let i = 0; i < encodings.length; ++i) {
   encodingsMap[encodings[i]] = i;
 }
@@ -2220,7 +2298,7 @@ export const encodingOps = {
 };
 
 export function getEncodingOps(encoding) {
-  encoding = String(encoding).toLowerCase();
+  encoding = StringPrototypeToLowerCase(String(encoding));
   switch (encoding.length) {
     case 4:
       if (encoding === "utf8") return encodingOps.utf8;
@@ -2260,6 +2338,14 @@ export function getEncodingOps(encoding) {
   }
 }
 
+/**
+ * @param {Buffer} source
+ * @param {Buffer} target
+ * @param {number} targetStart
+ * @param {number} sourceStart
+ * @param {number} sourceEnd
+ * @returns {number}
+ */
 export function _copyActual(
   source,
   target,
@@ -2278,6 +2364,7 @@ export function _copyActual(
   }
 
   if (sourceStart !== 0 || sourceEnd < source.length) {
+    // deno-lint-ignore prefer-primordials
     source = new Uint8Array(source.buffer, source.byteOffset + sourceStart, nb);
   }
 
@@ -2287,7 +2374,7 @@ export function _copyActual(
 }
 
 export function boundsError(value, length, type) {
-  if (Math.floor(value) !== value) {
+  if (MathFloor(value) !== value) {
     validateNumber(value, type);
     throw new codes.ERR_OUT_OF_RANGE(type || "offset", "an integer", value);
   }
@@ -2310,7 +2397,7 @@ export function validateNumber(value, name, min = undefined, max) {
 
   if (
     (min != null && value < min) || (max != null && value > max) ||
-    ((min != null || max != null) && Number.isNaN(value))
+    ((min != null || max != null) && NumberIsNaN(value))
   ) {
     throw new codes.ERR_OUT_OF_RANGE(
       name,
@@ -2344,11 +2431,11 @@ function checkInt(value, min, max, buf, offset, byteLength) {
 export function toInteger(n, defaultVal) {
   n = +n;
   if (
-    !Number.isNaN(n) &&
-    n >= Number.MIN_SAFE_INTEGER &&
-    n <= Number.MAX_SAFE_INTEGER
+    !NumberIsNaN(n) &&
+    n >= NumberMIN_SAFE_INTEGER &&
+    n <= NumberMAX_SAFE_INTEGER
   ) {
-    return ((n % 1) === 0 ? n : Math.floor(n));
+    return ((n % 1) === 0 ? n : MathFloor(n));
   }
   return defaultVal;
 }
@@ -2421,7 +2508,7 @@ export function writeU_Int48BE(buf, value, offset, min, max) {
   value = +value;
   checkInt(value, min, max, buf, offset, 5);
 
-  const newVal = Math.floor(value * 2 ** -32);
+  const newVal = MathFloor(value * 2 ** -32);
   buf[offset++] = newVal >>> 8;
   buf[offset++] = newVal;
   buf[offset + 3] = value;
@@ -2439,7 +2526,7 @@ export function writeU_Int40BE(buf, value, offset, min, max) {
   value = +value;
   checkInt(value, min, max, buf, offset, 4);
 
-  buf[offset++] = Math.floor(value * 2 ** -32);
+  buf[offset++] = MathFloor(value * 2 ** -32);
   buf[offset + 3] = value;
   value = value >>> 8;
   buf[offset + 2] = value;
@@ -2482,12 +2569,12 @@ export function validateOffset(
   value,
   name,
   min = 0,
-  max = Number.MAX_SAFE_INTEGER,
+  max = NumberMAX_SAFE_INTEGER,
 ) {
   if (typeof value !== "number") {
     throw new codes.ERR_INVALID_ARG_TYPE(name, "number", value);
   }
-  if (!Number.isInteger(value)) {
+  if (!NumberIsInteger(value)) {
     throw new codes.ERR_OUT_OF_RANGE(name, "an integer", value);
   }
   if (value < min || value > max) {
@@ -2500,7 +2587,7 @@ export function writeU_Int48LE(buf, value, offset, min, max) {
   value = +value;
   checkInt(value, min, max, buf, offset, 5);
 
-  const newVal = Math.floor(value * 2 ** -32);
+  const newVal = MathFloor(value * 2 ** -32);
   buf[offset++] = value;
   value = value >>> 8;
   buf[offset++] = value;
@@ -2526,7 +2613,7 @@ export function writeU_Int40LE(buf, value, offset, min, max) {
   buf[offset++] = value;
   value = value >>> 8;
   buf[offset++] = value;
-  buf[offset++] = Math.floor(newVal * 2 ** -32);
+  buf[offset++] = MathFloor(newVal * 2 ** -32);
   return offset;
 }
 
@@ -2560,14 +2647,14 @@ export function writeU_Int24LE(buf, value, offset, min, max) {
 
 export function isUtf8(input) {
   if (isTypedArray(input)) {
-    if (input.buffer.detached) {
+    if (isDetachedBuffer(TypedArrayPrototypeGetBuffer(input))) {
       throw new ERR_INVALID_STATE("Cannot validate on a detached buffer");
     }
     return op_is_utf8(input);
   }
 
   if (isAnyArrayBuffer(input)) {
-    if (input.detached) {
+    if (isDetachedBuffer(input)) {
       throw new ERR_INVALID_STATE("Cannot validate on a detached buffer");
     }
     return op_is_utf8(new Uint8Array(input));
@@ -2582,14 +2669,14 @@ export function isUtf8(input) {
 
 export function isAscii(input) {
   if (isTypedArray(input)) {
-    if (input.buffer.detached) {
+    if (isDetachedBuffer(TypedArrayPrototypeGetBuffer(input))) {
       throw new ERR_INVALID_STATE("Cannot validate on a detached buffer");
     }
     return op_is_ascii(input);
   }
 
   if (isAnyArrayBuffer(input)) {
-    if (input.detached) {
+    if (isDetachedBuffer(input)) {
       throw new ERR_INVALID_STATE("Cannot validate on a detached buffer");
     }
     return op_is_ascii(new Uint8Array(input));
@@ -2636,7 +2723,7 @@ export function transcode(source, fromEnco, toEnco) {
     const result = op_transcode(new Uint8Array(source), fromEnco, toEnco);
     return Buffer.from(result, toEnco);
   } catch (err) {
-    if (err.message.includes("Unable to transcode Buffer")) {
+    if (StringPrototypeIncludes(err.message, "Unable to transcode Buffer")) {
       throw illegalArgumentError;
     } else {
       throw err;
diff --git a/ext/node/polyfills/internal/child_process.ts b/ext/node/polyfills/internal/child_process.ts
index 6f209b7192..cfff1079ff 100644
--- a/ext/node/polyfills/internal/child_process.ts
+++ b/ext/node/polyfills/internal/child_process.ts
@@ -1191,8 +1191,12 @@ function toDenoArgs(args: string[]): string[] {
     }
 
     if (flagInfo === undefined) {
-      // Not a known flag that expects a value. Just copy it to the output.
-      denoArgs.push(arg);
+      if (arg === "--no-warnings") {
+        denoArgs.push("--quiet");
+      } else {
+        // Not a known flag that expects a value. Just copy it to the output.
+        denoArgs.push(arg);
+      }
       continue;
     }
 
@@ -1335,7 +1339,7 @@ export function setupChannel(target: any, ipc: number) {
           }
         }
 
-        process.nextTick(handleMessage, msg);
+        nextTick(handleMessage, msg);
       }
     } catch (err) {
       if (
@@ -1396,7 +1400,7 @@ export function setupChannel(target: any, ipc: number) {
     if (!target.connected) {
       const err = new ERR_IPC_CHANNEL_CLOSED();
       if (typeof callback === "function") {
-        process.nextTick(callback, err);
+        nextTick(callback, err);
       } else {
         nextTick(() => target.emit("error", err));
       }
@@ -1412,7 +1416,18 @@ export function setupChannel(target: any, ipc: number) {
       .then(() => {
         control.unrefCounted();
         if (callback) {
-          process.nextTick(callback, null);
+          nextTick(callback, null);
+        }
+      }, (err: Error) => {
+        control.unrefCounted();
+        if (err instanceof Deno.errors.Interrupted) {
+          // Channel closed on us mid-write.
+        } else {
+          if (typeof callback === "function") {
+            nextTick(callback, err);
+          } else {
+            nextTick(() => target.emit("error", err));
+          }
         }
       });
     return queueOk[0];
@@ -1429,7 +1444,7 @@ export function setupChannel(target: any, ipc: number) {
     target.connected = false;
     target[kCanDisconnect] = false;
     control[kControlDisconnect]();
-    process.nextTick(() => {
+    nextTick(() => {
       target.channel = null;
       core.close(ipc);
       target.emit("disconnect");
diff --git a/ext/node/polyfills/internal/crypto/_randomInt.ts b/ext/node/polyfills/internal/crypto/_randomInt.ts
index 7f4d703ad4..e08b3e9639 100644
--- a/ext/node/polyfills/internal/crypto/_randomInt.ts
+++ b/ext/node/polyfills/internal/crypto/_randomInt.ts
@@ -1,9 +1,15 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-// TODO(petamoriken): enable prefer-primordials for node polyfills
-// deno-lint-ignore-file prefer-primordials
-
 import { op_node_random_int } from "ext:core/ops";
+import { primordials } from "ext:core/mod.js";
+const {
+  Error,
+  MathCeil,
+  MathFloor,
+  MathPow,
+  NumberIsSafeInteger,
+  RangeError,
+} = primordials;
 
 export default function randomInt(max: number): number;
 export default function randomInt(min: number, max: number): number;
@@ -23,7 +29,9 @@ export default function randomInt(
   cb?: (err: Error | null, n?: number) => void,
 ): number | void {
   if (typeof max === "number" && typeof min === "number") {
-    [max, min] = [min, max];
+    const temp = max;
+    max = min;
+    min = temp;
   }
   if (min === undefined) min = 0;
   else if (typeof min === "function") {
@@ -32,13 +40,13 @@ export default function randomInt(
   }
 
   if (
-    !Number.isSafeInteger(min) ||
-    typeof max === "number" && !Number.isSafeInteger(max)
+    !NumberIsSafeInteger(min) ||
+    typeof max === "number" && !NumberIsSafeInteger(max)
   ) {
     throw new Error("max or min is not a Safe Number");
   }
 
-  if (max - min > Math.pow(2, 48)) {
+  if (max - min > MathPow(2, 48)) {
     throw new RangeError("max - min should be less than 2^48!");
   }
 
@@ -46,8 +54,8 @@ export default function randomInt(
     throw new Error("Min is bigger than Max!");
   }
 
-  min = Math.ceil(min);
-  max = Math.floor(max);
+  min = MathCeil(min);
+  max = MathFloor(max);
   const result = op_node_random_int(min, max);
 
   if (cb) {
diff --git a/ext/node/polyfills/internal/errors.ts b/ext/node/polyfills/internal/errors.ts
index 51bd7a0250..5a3d4437a1 100644
--- a/ext/node/polyfills/internal/errors.ts
+++ b/ext/node/polyfills/internal/errors.ts
@@ -2558,19 +2558,6 @@ export class ERR_FS_RMDIR_ENOTDIR extends NodeSystemError {
   }
 }
 
-export class ERR_OS_NO_HOMEDIR extends NodeSystemError {
-  constructor() {
-    const code = isWindows ? "ENOENT" : "ENOTDIR";
-    const ctx: NodeSystemErrorCtx = {
-      message: "not a directory",
-      syscall: "home",
-      code,
-      errno: isWindows ? osConstants.errno.ENOENT : osConstants.errno.ENOTDIR,
-    };
-    super(code, ctx, "Path is not a directory");
-  }
-}
-
 export class ERR_HTTP_SOCKET_ASSIGNED extends NodeError {
   constructor() {
     super(
diff --git a/ext/node/polyfills/internal/util/inspect.mjs b/ext/node/polyfills/internal/util/inspect.mjs
index 3a61c387c0..ae797449bf 100644
--- a/ext/node/polyfills/internal/util/inspect.mjs
+++ b/ext/node/polyfills/internal/util/inspect.mjs
@@ -565,6 +565,19 @@ export function stripVTControlCharacters(str) {
 
 export function styleText(format, text) {
   validateString(text, "text");
+
+  if (Array.isArray(format)) {
+    for (let i = 0; i < format.length; i++) {
+      const item = format[i];
+      const formatCodes = inspect.colors[item];
+      if (formatCodes == null) {
+        validateOneOf(item, "format", Object.keys(inspect.colors));
+      }
+      text = `\u001b[${formatCodes[0]}m${text}\u001b[${formatCodes[1]}m`;
+    }
+    return text;
+  }
+
   const formatCodes = inspect.colors[format];
   if (formatCodes == null) {
     validateOneOf(format, "format", Object.keys(inspect.colors));
diff --git a/ext/node/polyfills/internal_binding/_timingSafeEqual.ts b/ext/node/polyfills/internal_binding/_timingSafeEqual.ts
index ff141fdbfc..559b7685b8 100644
--- a/ext/node/polyfills/internal_binding/_timingSafeEqual.ts
+++ b/ext/node/polyfills/internal_binding/_timingSafeEqual.ts
@@ -5,10 +5,11 @@
 
 import { Buffer } from "node:buffer";
 
-function assert(cond) {
-  if (!cond) {
-    throw new Error("assertion failed");
+function toDataView(ab: ArrayBufferLike | ArrayBufferView): DataView {
+  if (ArrayBuffer.isView(ab)) {
+    return new DataView(ab.buffer, ab.byteOffset, ab.byteLength);
   }
+  return new DataView(ab);
 }
 
 /** Compare to array buffers or data views in a way that timing based attacks
@@ -21,13 +22,11 @@ function stdTimingSafeEqual(
     return false;
   }
   if (!(a instanceof DataView)) {
-    a = new DataView(ArrayBuffer.isView(a) ? a.buffer : a);
+    a = toDataView(a);
   }
   if (!(b instanceof DataView)) {
-    b = new DataView(ArrayBuffer.isView(b) ? b.buffer : b);
+    b = toDataView(b);
   }
-  assert(a instanceof DataView);
-  assert(b instanceof DataView);
   const length = a.byteLength;
   let out = 0;
   let i = -1;
@@ -41,7 +40,11 @@ export const timingSafeEqual = (
   a: Buffer | DataView | ArrayBuffer,
   b: Buffer | DataView | ArrayBuffer,
 ): boolean => {
-  if (a instanceof Buffer) a = new DataView(a.buffer);
-  if (a instanceof Buffer) b = new DataView(a.buffer);
+  if (a instanceof Buffer) {
+    a = new DataView(a.buffer, a.byteOffset, a.byteLength);
+  }
+  if (b instanceof Buffer) {
+    b = new DataView(b.buffer, b.byteOffset, b.byteLength);
+  }
   return stdTimingSafeEqual(a, b);
 };
diff --git a/ext/node/polyfills/internal_binding/http_parser.ts b/ext/node/polyfills/internal_binding/http_parser.ts
new file mode 100644
index 0000000000..ca4f896e20
--- /dev/null
+++ b/ext/node/polyfills/internal_binding/http_parser.ts
@@ -0,0 +1,159 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+// Copyright Joyent, Inc. and other Node contributors.
+//
+// Permission is hereby granted, free of charge, to any person obtaining a
+// copy of this software and associated documentation files (the
+// "Software"), to deal in the Software without restriction, including
+// without limitation the rights to use, copy, modify, merge, publish,
+// distribute, sublicense, and/or sell copies of the Software, and to permit
+// persons to whom the Software is furnished to do so, subject to the
+// following conditions:
+//
+// The above copyright notice and this permission notice shall be included
+// in all copies or substantial portions of the Software.
+//
+// THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS
+// OR IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF
+// MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN
+// NO EVENT SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM,
+// DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR
+// OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE
+// USE OR OTHER DEALINGS IN THE SOFTWARE.
+
+import { primordials } from "ext:core/mod.js";
+import { AsyncWrap } from "ext:deno_node/internal_binding/async_wrap.ts";
+
+const {
+  ObjectDefineProperty,
+  ObjectEntries,
+  ObjectSetPrototypeOf,
+  SafeArrayIterator,
+} = primordials;
+
+export const methods = [
+  "DELETE",
+  "GET",
+  "HEAD",
+  "POST",
+  "PUT",
+  "CONNECT",
+  "OPTIONS",
+  "TRACE",
+  "COPY",
+  "LOCK",
+  "MKCOL",
+  "MOVE",
+  "PROPFIND",
+  "PROPPATCH",
+  "SEARCH",
+  "UNLOCK",
+  "BIND",
+  "REBIND",
+  "UNBIND",
+  "ACL",
+  "REPORT",
+  "MKACTIVITY",
+  "CHECKOUT",
+  "MERGE",
+  "M-SEARCH",
+  "NOTIFY",
+  "SUBSCRIBE",
+  "UNSUBSCRIBE",
+  "PATCH",
+  "PURGE",
+  "MKCALENDAR",
+  "LINK",
+  "UNLINK",
+  "SOURCE",
+  "QUERY",
+];
+
+export const allMethods = [
+  "DELETE",
+  "GET",
+  "HEAD",
+  "POST",
+  "PUT",
+  "CONNECT",
+  "OPTIONS",
+  "TRACE",
+  "COPY",
+  "LOCK",
+  "MKCOL",
+  "MOVE",
+  "PROPFIND",
+  "PROPPATCH",
+  "SEARCH",
+  "UNLOCK",
+  "BIND",
+  "REBIND",
+  "UNBIND",
+  "ACL",
+  "REPORT",
+  "MKACTIVITY",
+  "CHECKOUT",
+  "MERGE",
+  "M-SEARCH",
+  "NOTIFY",
+  "SUBSCRIBE",
+  "UNSUBSCRIBE",
+  "PATCH",
+  "PURGE",
+  "MKCALENDAR",
+  "LINK",
+  "UNLINK",
+  "SOURCE",
+  "PRI",
+  "DESCRIBE",
+  "ANNOUNCE",
+  "SETUP",
+  "PLAY",
+  "PAUSE",
+  "TEARDOWN",
+  "GET_PARAMETER",
+  "SET_PARAMETER",
+  "REDIRECT",
+  "RECORD",
+  "FLUSH",
+  "QUERY",
+];
+
+export function HTTPParser() {
+}
+
+ObjectSetPrototypeOf(HTTPParser.prototype, AsyncWrap.prototype);
+
+function defineProps(obj: object, props: Record<string, unknown>) {
+  for (const entry of new SafeArrayIterator(ObjectEntries(props))) {
+    ObjectDefineProperty(obj, entry[0], {
+      value: entry[1],
+      enumerable: true,
+      writable: true,
+      configurable: true,
+    });
+  }
+}
+
+defineProps(HTTPParser, {
+  REQUEST: 1,
+  RESPONSE: 2,
+  kOnMessageBegin: 0,
+  kOnHeaders: 1,
+  kOnHeadersComplete: 2,
+  kOnBody: 3,
+  kOnMessageComplete: 4,
+  kOnExecute: 5,
+  kOnTimeout: 6,
+  kLenientNone: 0,
+  kLenientHeaders: 1,
+  kLenientChunkedLength: 2,
+  kLenientKeepAlive: 4,
+  kLenientTransferEncoding: 8,
+  kLenientVersion: 16,
+  kLenientDataAfterClose: 32,
+  kLenientOptionalLFAfterCR: 64,
+  kLenientOptionalCRLFAfterChunk: 128,
+  kLenientOptionalCRBeforeLF: 256,
+  kLenientSpacesAfterChunkSize: 512,
+  kLenientAll: 1023,
+});
diff --git a/ext/node/polyfills/internal_binding/mod.ts b/ext/node/polyfills/internal_binding/mod.ts
index f2d7f55bc7..ebbfc629f1 100644
--- a/ext/node/polyfills/internal_binding/mod.ts
+++ b/ext/node/polyfills/internal_binding/mod.ts
@@ -17,6 +17,7 @@ import * as types from "ext:deno_node/internal_binding/types.ts";
 import * as udpWrap from "ext:deno_node/internal_binding/udp_wrap.ts";
 import * as util from "ext:deno_node/internal_binding/util.ts";
 import * as uv from "ext:deno_node/internal_binding/uv.ts";
+import * as httpParser from "ext:deno_node/internal_binding/http_parser.ts";
 
 const modules = {
   "async_wrap": asyncWrap,
@@ -32,7 +33,7 @@ const modules = {
   "fs_dir": {},
   "fs_event_wrap": {},
   "heap_utils": {},
-  "http_parser": {},
+  "http_parser": httpParser,
   icu: {},
   inspector: {},
   "js_stream": {},
diff --git a/ext/node/polyfills/internal_binding/tcp_wrap.ts b/ext/node/polyfills/internal_binding/tcp_wrap.ts
index 973a1d1c01..d9f1c5356a 100644
--- a/ext/node/polyfills/internal_binding/tcp_wrap.ts
+++ b/ext/node/polyfills/internal_binding/tcp_wrap.ts
@@ -299,8 +299,10 @@ export class TCP extends ConnectionWrap {
    * @param noDelay
    * @return An error status code.
    */
-  setNoDelay(_noDelay: boolean): number {
-    // TODO(bnoordhuis) https://github.com/denoland/deno/pull/13103
+  setNoDelay(noDelay: boolean): number {
+    if (this[kStreamBaseField] && "setNoDelay" in this[kStreamBaseField]) {
+      this[kStreamBaseField].setNoDelay(noDelay);
+    }
     return 0;
   }
 
diff --git a/ext/node/polyfills/os.ts b/ext/node/polyfills/os.ts
index e47e8679ec..edc89ed2c3 100644
--- a/ext/node/polyfills/os.ts
+++ b/ext/node/polyfills/os.ts
@@ -28,16 +28,17 @@ import {
   op_homedir,
   op_node_os_get_priority,
   op_node_os_set_priority,
-  op_node_os_username,
+  op_node_os_user_info,
 } from "ext:core/ops";
 
 import { validateIntegerRange } from "ext:deno_node/_utils.ts";
 import process from "node:process";
 import { isWindows } from "ext:deno_node/_util/os.ts";
-import { ERR_OS_NO_HOMEDIR } from "ext:deno_node/internal/errors.ts";
 import { os } from "ext:deno_node/internal_binding/constants.ts";
 import { osUptime } from "ext:runtime/30_os.js";
 import { Buffer } from "ext:deno_node/internal/buffer.mjs";
+import { primordials } from "ext:core/mod.js";
+const { StringPrototypeEndsWith, StringPrototypeSlice } = primordials;
 
 export const constants = os;
 
@@ -136,6 +137,8 @@ export function arch(): string {
 (uptime as any)[Symbol.toPrimitive] = (): number => uptime();
 // deno-lint-ignore no-explicit-any
 (machine as any)[Symbol.toPrimitive] = (): string => machine();
+// deno-lint-ignore no-explicit-any
+(tmpdir as any)[Symbol.toPrimitive] = (): string | null => tmpdir();
 
 export function cpus(): CPUCoreInfo[] {
   return op_cpus();
@@ -268,26 +271,27 @@ export function setPriority(pid: number, priority?: number) {
 export function tmpdir(): string | null {
   /* This follows the node js implementation, but has a few
      differences:
-     * On windows, if none of the environment variables are defined,
-       we return null.
-     * On unix we use a plain Deno.env.get, instead of safeGetenv,
+     * We use a plain Deno.env.get, instead of safeGetenv,
        which special cases setuid binaries.
-     * Node removes a single trailing / or \, we remove all.
   */
   if (isWindows) {
-    const temp = Deno.env.get("TEMP") || Deno.env.get("TMP");
-    if (temp) {
-      return temp.replace(/(?<!:)[/\\]*$/, "");
+    let temp = Deno.env.get("TEMP") || Deno.env.get("TMP") ||
+      (Deno.env.get("SystemRoot") || Deno.env.get("windir")) + "\\temp";
+    if (
+      temp.length > 1 && StringPrototypeEndsWith(temp, "\\") &&
+      !StringPrototypeEndsWith(temp, ":\\")
+    ) {
+      temp = StringPrototypeSlice(temp, 0, -1);
     }
-    const base = Deno.env.get("SYSTEMROOT") || Deno.env.get("WINDIR");
-    if (base) {
-      return base + "\\temp";
-    }
-    return null;
+
+    return temp;
   } else { // !isWindows
-    const temp = Deno.env.get("TMPDIR") || Deno.env.get("TMP") ||
+    let temp = Deno.env.get("TMPDIR") || Deno.env.get("TMP") ||
       Deno.env.get("TEMP") || "/tmp";
-    return temp.replace(/(?<!^)\/*$/, "");
+    if (temp.length > 1 && StringPrototypeEndsWith(temp, "/")) {
+      temp = StringPrototypeSlice(temp, 0, -1);
+    }
+    return temp;
   }
 }
 
@@ -320,7 +324,6 @@ export function uptime(): number {
   return osUptime();
 }
 
-/** Not yet implemented */
 export function userInfo(
   options: UserInfoOptions = { encoding: "utf-8" },
 ): UserInfo {
@@ -331,20 +334,10 @@ export function userInfo(
     uid = -1;
     gid = -1;
   }
-
-  // TODO(@crowlKats): figure out how to do this correctly:
-  //  The value of homedir returned by os.userInfo() is provided by the operating system.
-  //  This differs from the result of os.homedir(), which queries environment
-  //  variables for the home directory before falling back to the operating system response.
-  let _homedir = homedir();
-  if (!_homedir) {
-    throw new ERR_OS_NO_HOMEDIR();
-  }
-  let shell = isWindows ? null : (Deno.env.get("SHELL") || null);
-  let username = op_node_os_username();
+  let { username, homedir, shell } = op_node_os_user_info(uid);
 
   if (options?.encoding === "buffer") {
-    _homedir = _homedir ? Buffer.from(_homedir) : _homedir;
+    homedir = homedir ? Buffer.from(homedir) : homedir;
     shell = shell ? Buffer.from(shell) : shell;
     username = Buffer.from(username);
   }
@@ -352,7 +345,7 @@ export function userInfo(
   return {
     uid,
     gid,
-    homedir: _homedir,
+    homedir,
     shell,
     username,
   };
diff --git a/ext/node/polyfills/process.ts b/ext/node/polyfills/process.ts
index 3dc6ce61aa..2605fa6d1a 100644
--- a/ext/node/polyfills/process.ts
+++ b/ext/node/polyfills/process.ts
@@ -520,9 +520,7 @@ Process.prototype.on = function (
     } else if (
       event !== "SIGBREAK" && event !== "SIGINT" && Deno.build.os === "windows"
     ) {
-      // Ignores all signals except SIGBREAK and SIGINT on windows.
-      // deno-lint-ignore no-console
-      console.warn(`Ignoring signal "${event}" on Windows`);
+      // TODO(#26331): Ignores all signals except SIGBREAK and SIGINT on windows.
     } else {
       EventEmitter.prototype.on.call(this, event, listener);
       Deno.addSignalListener(event as Deno.Signal, listener);
diff --git a/ext/node/polyfills/util.ts b/ext/node/polyfills/util.ts
index 586fae17e9..d82b288b03 100644
--- a/ext/node/polyfills/util.ts
+++ b/ext/node/polyfills/util.ts
@@ -39,6 +39,7 @@ import {
   formatWithOptions,
   inspect,
   stripVTControlCharacters,
+  styleText,
 } from "ext:deno_node/internal/util/inspect.mjs";
 import { codes } from "ext:deno_node/internal/error_codes.ts";
 import types from "node:util/types";
@@ -63,6 +64,7 @@ export {
   parseArgs,
   promisify,
   stripVTControlCharacters,
+  styleText,
   types,
 };
 
@@ -354,4 +356,5 @@ export default {
   debuglog,
   debug: debuglog,
   isDeepStrictEqual,
+  styleText,
 };
diff --git a/ext/tls/Cargo.toml b/ext/tls/Cargo.toml
index 6c1554241e..6871faa5b8 100644
--- a/ext/tls/Cargo.toml
+++ b/ext/tls/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_tls"
-version = "0.158.0"
+version = "0.162.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -21,5 +21,6 @@ rustls-pemfile.workspace = true
 rustls-tokio-stream.workspace = true
 rustls-webpki.workspace = true
 serde.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
 webpki-roots.workspace = true
diff --git a/ext/tls/lib.rs b/ext/tls/lib.rs
index c4d548ccf2..883d2995e4 100644
--- a/ext/tls/lib.rs
+++ b/ext/tls/lib.rs
@@ -9,17 +9,12 @@ pub use rustls_tokio_stream::*;
 pub use webpki;
 pub use webpki_roots;
 
-use deno_core::anyhow::anyhow;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
-
 use rustls::client::danger::HandshakeSignatureValid;
 use rustls::client::danger::ServerCertVerified;
 use rustls::client::danger::ServerCertVerifier;
 use rustls::client::WebPkiServerVerifier;
 use rustls::ClientConfig;
 use rustls::DigitallySignedStruct;
-use rustls::Error;
 use rustls::RootCertStore;
 use rustls_pemfile::certs;
 use rustls_pemfile::ec_private_keys;
@@ -35,12 +30,30 @@ use std::sync::Arc;
 mod tls_key;
 pub use tls_key::*;
 
+#[derive(Debug, thiserror::Error)]
+pub enum TlsError {
+  #[error(transparent)]
+  Rustls(#[from] rustls::Error),
+  #[error("Unable to add pem file to certificate store: {0}")]
+  UnableAddPemFileToCert(std::io::Error),
+  #[error("Unable to decode certificate")]
+  CertInvalid,
+  #[error("No certificates found in certificate data")]
+  CertsNotFound,
+  #[error("No keys found in key data")]
+  KeysNotFound,
+  #[error("Unable to decode key")]
+  KeyDecode,
+}
+
 /// Lazily resolves the root cert store.
 ///
 /// This was done because the root cert store is not needed in all cases
 /// and takes a bit of time to initialize.
 pub trait RootCertStoreProvider: Send + Sync {
-  fn get_or_try_init(&self) -> Result<&RootCertStore, AnyError>;
+  fn get_or_try_init(
+    &self,
+  ) -> Result<&RootCertStore, deno_core::error::AnyError>;
 }
 
 // This extension has no runtime apis, it only exports some shared native functions.
@@ -77,7 +90,7 @@ impl ServerCertVerifier for NoCertificateVerification {
     server_name: &rustls::pki_types::ServerName<'_>,
     ocsp_response: &[u8],
     now: rustls::pki_types::UnixTime,
-  ) -> Result<ServerCertVerified, Error> {
+  ) -> Result<ServerCertVerified, rustls::Error> {
     if self.ic_allowlist.is_empty() {
       return Ok(ServerCertVerified::assertion());
     }
@@ -89,7 +102,9 @@ impl ServerCertVerifier for NoCertificateVerification {
       _ => {
         // NOTE(bartlomieju): `ServerName` is a non-exhaustive enum
         // so we have this catch all errors here.
-        return Err(Error::General("Unknown `ServerName` variant".to_string()));
+        return Err(rustls::Error::General(
+          "Unknown `ServerName` variant".to_string(),
+        ));
       }
     };
     if self.ic_allowlist.contains(&dns_name_or_ip_address) {
@@ -110,7 +125,7 @@ impl ServerCertVerifier for NoCertificateVerification {
     message: &[u8],
     cert: &rustls::pki_types::CertificateDer,
     dss: &DigitallySignedStruct,
-  ) -> Result<HandshakeSignatureValid, Error> {
+  ) -> Result<HandshakeSignatureValid, rustls::Error> {
     if self.ic_allowlist.is_empty() {
       return Ok(HandshakeSignatureValid::assertion());
     }
@@ -126,7 +141,7 @@ impl ServerCertVerifier for NoCertificateVerification {
     message: &[u8],
     cert: &rustls::pki_types::CertificateDer,
     dss: &DigitallySignedStruct,
-  ) -> Result<HandshakeSignatureValid, Error> {
+  ) -> Result<HandshakeSignatureValid, rustls::Error> {
     if self.ic_allowlist.is_empty() {
       return Ok(HandshakeSignatureValid::assertion());
     }
@@ -178,7 +193,7 @@ pub fn create_client_config(
   unsafely_ignore_certificate_errors: Option<Vec<String>>,
   maybe_cert_chain_and_key: TlsKeys,
   socket_use: SocketUse,
-) -> Result<ClientConfig, AnyError> {
+) -> Result<ClientConfig, TlsError> {
   if let Some(ic_allowlist) = unsafely_ignore_certificate_errors {
     let client_config = ClientConfig::builder()
       .dangerous()
@@ -214,10 +229,7 @@ pub fn create_client_config(
           root_cert_store.add(cert)?;
         }
         Err(e) => {
-          return Err(anyhow!(
-            "Unable to add pem file to certificate store: {}",
-            e
-          ));
+          return Err(TlsError::UnableAddPemFileToCert(e));
         }
       }
     }
@@ -255,74 +267,61 @@ fn add_alpn(client: &mut ClientConfig, socket_use: SocketUse) {
 
 pub fn load_certs(
   reader: &mut dyn BufRead,
-) -> Result<Vec<CertificateDer<'static>>, AnyError> {
+) -> Result<Vec<CertificateDer<'static>>, TlsError> {
   let certs: Result<Vec<_>, _> = certs(reader).collect();
 
-  let certs = certs
-    .map_err(|_| custom_error("InvalidData", "Unable to decode certificate"))?;
+  let certs = certs.map_err(|_| TlsError::CertInvalid)?;
 
   if certs.is_empty() {
-    return Err(cert_not_found_err());
+    return Err(TlsError::CertsNotFound);
   }
 
   Ok(certs)
 }
 
-fn key_decode_err() -> AnyError {
-  custom_error("InvalidData", "Unable to decode key")
-}
-
-fn key_not_found_err() -> AnyError {
-  custom_error("InvalidData", "No keys found in key data")
-}
-
-fn cert_not_found_err() -> AnyError {
-  custom_error("InvalidData", "No certificates found in certificate data")
-}
-
 /// Starts with -----BEGIN RSA PRIVATE KEY-----
 fn load_rsa_keys(
   mut bytes: &[u8],
-) -> Result<Vec<PrivateKeyDer<'static>>, AnyError> {
+) -> Result<Vec<PrivateKeyDer<'static>>, TlsError> {
   let keys: Result<Vec<_>, _> = rsa_private_keys(&mut bytes).collect();
-  let keys = keys.map_err(|_| key_decode_err())?;
+  let keys = keys.map_err(|_| TlsError::KeyDecode)?;
   Ok(keys.into_iter().map(PrivateKeyDer::Pkcs1).collect())
 }
 
 /// Starts with -----BEGIN EC PRIVATE KEY-----
 fn load_ec_keys(
   mut bytes: &[u8],
-) -> Result<Vec<PrivateKeyDer<'static>>, AnyError> {
+) -> Result<Vec<PrivateKeyDer<'static>>, TlsError> {
   let keys: Result<Vec<_>, std::io::Error> =
     ec_private_keys(&mut bytes).collect();
-  let keys2 = keys.map_err(|_| key_decode_err())?;
+  let keys2 = keys.map_err(|_| TlsError::KeyDecode)?;
   Ok(keys2.into_iter().map(PrivateKeyDer::Sec1).collect())
 }
 
 /// Starts with -----BEGIN PRIVATE KEY-----
 fn load_pkcs8_keys(
   mut bytes: &[u8],
-) -> Result<Vec<PrivateKeyDer<'static>>, AnyError> {
+) -> Result<Vec<PrivateKeyDer<'static>>, TlsError> {
   let keys: Result<Vec<_>, std::io::Error> =
     pkcs8_private_keys(&mut bytes).collect();
-  let keys2 = keys.map_err(|_| key_decode_err())?;
+  let keys2 = keys.map_err(|_| TlsError::KeyDecode)?;
   Ok(keys2.into_iter().map(PrivateKeyDer::Pkcs8).collect())
 }
 
 fn filter_invalid_encoding_err(
-  to_be_filtered: Result<HandshakeSignatureValid, Error>,
-) -> Result<HandshakeSignatureValid, Error> {
+  to_be_filtered: Result<HandshakeSignatureValid, rustls::Error>,
+) -> Result<HandshakeSignatureValid, rustls::Error> {
   match to_be_filtered {
-    Err(Error::InvalidCertificate(rustls::CertificateError::BadEncoding)) => {
-      Ok(HandshakeSignatureValid::assertion())
-    }
+    Err(rustls::Error::InvalidCertificate(
+      rustls::CertificateError::BadEncoding,
+    )) => Ok(HandshakeSignatureValid::assertion()),
     res => res,
   }
 }
 
 pub fn load_private_keys(
   bytes: &[u8],
-) -> Result<Vec<PrivateKeyDer<'static>>, AnyError> {
+) -> Result<Vec<PrivateKeyDer<'static>>, TlsError> {
   let mut keys = load_rsa_keys(bytes)?;
 
   if keys.is_empty() {
@@ -334,7 +333,7 @@ pub fn load_private_keys(
   }
 
   if keys.is_empty() {
-    return Err(key_not_found_err());
+    return Err(TlsError::KeysNotFound);
   }
 
   Ok(keys)
diff --git a/ext/tls/tls_key.rs b/ext/tls/tls_key.rs
index 66fac86f87..b7baa604b9 100644
--- a/ext/tls/tls_key.rs
+++ b/ext/tls/tls_key.rs
@@ -11,8 +11,6 @@
 //! key lookup can handle closing one end of the pair, in which case they will just
 //! attempt to clean up the associated resources.
 
-use deno_core::anyhow::anyhow;
-use deno_core::error::AnyError;
 use deno_core::futures::future::poll_fn;
 use deno_core::futures::future::Either;
 use deno_core::futures::FutureExt;
@@ -33,7 +31,19 @@ use tokio::sync::oneshot;
 use webpki::types::CertificateDer;
 use webpki::types::PrivateKeyDer;
 
-type ErrorType = Rc<AnyError>;
+#[derive(Debug, thiserror::Error)]
+pub enum TlsKeyError {
+  #[error(transparent)]
+  Rustls(#[from] rustls::Error),
+  #[error("Failed: {0}")]
+  Failed(ErrorType),
+  #[error(transparent)]
+  JoinError(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  RecvError(#[from] tokio::sync::broadcast::error::RecvError),
+}
+
+type ErrorType = Arc<Box<str>>;
 
 /// A TLS certificate/private key pair.
 /// see https://docs.rs/rustls-pki-types/latest/rustls_pki_types/#cloning-private-keys
@@ -114,7 +124,7 @@ impl TlsKeyResolver {
     &self,
     sni: String,
     alpn: Vec<Vec<u8>>,
-  ) -> Result<Arc<ServerConfig>, AnyError> {
+  ) -> Result<Arc<ServerConfig>, TlsKeyError> {
     let key = self.resolve(sni).await?;
 
     let mut tls_config = ServerConfig::builder()
@@ -183,7 +193,7 @@ impl TlsKeyResolver {
   pub fn resolve(
     &self,
     sni: String,
-  ) -> impl Future<Output = Result<TlsKey, AnyError>> {
+  ) -> impl Future<Output = Result<TlsKey, TlsKeyError>> {
     let mut cache = self.inner.cache.borrow_mut();
     let mut recv = match cache.get(&sni) {
       None => {
@@ -194,7 +204,7 @@ impl TlsKeyResolver {
       }
       Some(TlsKeyState::Resolving(recv)) => recv.resubscribe(),
       Some(TlsKeyState::Resolved(res)) => {
-        return Either::Left(ready(res.clone().map_err(|_| anyhow!("Failed"))));
+        return Either::Left(ready(res.clone().map_err(TlsKeyError::Failed)));
       }
     };
     drop(cache);
@@ -212,7 +222,7 @@ impl TlsKeyResolver {
           // Someone beat us to it
         }
       }
-      res.map_err(|_| anyhow!("Failed"))
+      res.map_err(TlsKeyError::Failed)
     });
     Either::Right(async move { handle.await? })
   }
@@ -247,13 +257,13 @@ impl TlsKeyLookup {
   }
 
   /// Resolve a previously polled item.
-  pub fn resolve(&self, sni: String, res: Result<TlsKey, AnyError>) {
+  pub fn resolve(&self, sni: String, res: Result<TlsKey, String>) {
     _ = self
       .pending
       .borrow_mut()
       .remove(&sni)
       .unwrap()
-      .send(res.map_err(Rc::new));
+      .send(res.map_err(|e| Arc::new(e.into_boxed_str())));
   }
 }
 
diff --git a/ext/url/Cargo.toml b/ext/url/Cargo.toml
index 13aca99539..24d81abf83 100644
--- a/ext/url/Cargo.toml
+++ b/ext/url/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_url"
-version = "0.171.0"
+version = "0.175.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -15,6 +15,7 @@ path = "lib.rs"
 
 [dependencies]
 deno_core.workspace = true
+thiserror.workspace = true
 urlpattern = "0.3.0"
 
 [dev-dependencies]
diff --git a/ext/url/lib.rs b/ext/url/lib.rs
index 6869d656b5..f8946532ae 100644
--- a/ext/url/lib.rs
+++ b/ext/url/lib.rs
@@ -15,6 +15,8 @@ use std::path::PathBuf;
 use crate::urlpattern::op_urlpattern_parse;
 use crate::urlpattern::op_urlpattern_process_match_input;
 
+pub use urlpattern::UrlPatternError;
+
 deno_core::extension!(
   deno_url,
   deps = [deno_webidl],
diff --git a/ext/url/urlpattern.rs b/ext/url/urlpattern.rs
index b6d9a13828..7d4e8ee71b 100644
--- a/ext/url/urlpattern.rs
+++ b/ext/url/urlpattern.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 
 use urlpattern::quirks;
@@ -9,21 +7,23 @@ use urlpattern::quirks::MatchInput;
 use urlpattern::quirks::StringOrInit;
 use urlpattern::quirks::UrlPattern;
 
+#[derive(Debug, thiserror::Error)]
+#[error(transparent)]
+pub struct UrlPatternError(urlpattern::Error);
+
 #[op2]
 #[serde]
 pub fn op_urlpattern_parse(
   #[serde] input: StringOrInit,
   #[string] base_url: Option<String>,
   #[serde] options: urlpattern::UrlPatternOptions,
-) -> Result<UrlPattern, AnyError> {
-  let init = urlpattern::quirks::process_construct_pattern_input(
-    input,
-    base_url.as_deref(),
-  )
-  .map_err(|e| type_error(e.to_string()))?;
+) -> Result<UrlPattern, UrlPatternError> {
+  let init =
+    quirks::process_construct_pattern_input(input, base_url.as_deref())
+      .map_err(UrlPatternError)?;
 
-  let pattern = urlpattern::quirks::parse_pattern(init, options)
-    .map_err(|e| type_error(e.to_string()))?;
+  let pattern =
+    quirks::parse_pattern(init, options).map_err(UrlPatternError)?;
 
   Ok(pattern)
 }
@@ -33,14 +33,14 @@ pub fn op_urlpattern_parse(
 pub fn op_urlpattern_process_match_input(
   #[serde] input: StringOrInit,
   #[string] base_url: Option<String>,
-) -> Result<Option<(MatchInput, quirks::Inputs)>, AnyError> {
-  let res = urlpattern::quirks::process_match_input(input, base_url.as_deref())
-    .map_err(|e| type_error(e.to_string()))?;
+) -> Result<Option<(MatchInput, quirks::Inputs)>, UrlPatternError> {
+  let res = quirks::process_match_input(input, base_url.as_deref())
+    .map_err(UrlPatternError)?;
 
   let (input, inputs) = match res {
     Some((input, inputs)) => (input, inputs),
     None => return Ok(None),
   };
 
-  Ok(urlpattern::quirks::parse_match_input(input).map(|input| (input, inputs)))
+  Ok(quirks::parse_match_input(input).map(|input| (input, inputs)))
 }
diff --git a/ext/web/Cargo.toml b/ext/web/Cargo.toml
index 4120e978e0..a02cff98fc 100644
--- a/ext/web/Cargo.toml
+++ b/ext/web/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_web"
-version = "0.202.0"
+version = "0.206.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -23,6 +23,7 @@ encoding_rs.workspace = true
 flate2 = { workspace = true, features = ["default"] }
 futures.workspace = true
 serde = "1.0.149"
+thiserror.workspace = true
 tokio.workspace = true
 uuid = { workspace = true, features = ["serde"] }
 
diff --git a/ext/web/blob.rs b/ext/web/blob.rs
index 392f36acb8..bc64a0f27e 100644
--- a/ext/web/blob.rs
+++ b/ext/web/blob.rs
@@ -7,8 +7,6 @@ use std::rc::Rc;
 use std::sync::Arc;
 
 use async_trait::async_trait;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::parking_lot::Mutex;
 use deno_core::url::Url;
@@ -19,6 +17,18 @@ use serde::Deserialize;
 use serde::Serialize;
 use uuid::Uuid;
 
+#[derive(Debug, thiserror::Error)]
+pub enum BlobError {
+  #[error("Blob part not found")]
+  BlobPartNotFound,
+  #[error("start + len can not be larger than blob part size")]
+  SizeLargerThanBlobPart,
+  #[error("Blob URLs are not supported in this context")]
+  BlobURLsNotSupported,
+  #[error(transparent)]
+  Url(#[from] deno_core::url::ParseError),
+}
+
 use crate::Location;
 
 pub type PartMap = HashMap<Uuid, Arc<dyn BlobPart + Send + Sync>>;
@@ -96,18 +106,18 @@ pub struct Blob {
 
 impl Blob {
   // TODO(lucacsonato): this should be a stream!
-  pub async fn read_all(&self) -> Result<Vec<u8>, AnyError> {
+  pub async fn read_all(&self) -> Vec<u8> {
     let size = self.size();
     let mut bytes = Vec::with_capacity(size);
 
     for part in &self.parts {
-      let chunk = part.read().await?;
+      let chunk = part.read().await;
       bytes.extend_from_slice(chunk);
     }
 
     assert_eq!(bytes.len(), size);
 
-    Ok(bytes)
+    bytes
   }
 
   fn size(&self) -> usize {
@@ -122,7 +132,7 @@ impl Blob {
 #[async_trait]
 pub trait BlobPart: Debug {
   // TODO(lucacsonato): this should be a stream!
-  async fn read(&self) -> Result<&[u8], AnyError>;
+  async fn read(&self) -> &[u8];
   fn size(&self) -> usize;
 }
 
@@ -137,8 +147,8 @@ impl From<Vec<u8>> for InMemoryBlobPart {
 
 #[async_trait]
 impl BlobPart for InMemoryBlobPart {
-  async fn read(&self) -> Result<&[u8], AnyError> {
-    Ok(&self.0)
+  async fn read(&self) -> &[u8] {
+    &self.0
   }
 
   fn size(&self) -> usize {
@@ -155,9 +165,9 @@ pub struct SlicedBlobPart {
 
 #[async_trait]
 impl BlobPart for SlicedBlobPart {
-  async fn read(&self) -> Result<&[u8], AnyError> {
-    let original = self.part.read().await?;
-    Ok(&original[self.start..self.start + self.len])
+  async fn read(&self) -> &[u8] {
+    let original = self.part.read().await;
+    &original[self.start..self.start + self.len]
   }
 
   fn size(&self) -> usize {
@@ -189,19 +199,17 @@ pub fn op_blob_slice_part(
   state: &mut OpState,
   #[serde] id: Uuid,
   #[serde] options: SliceOptions,
-) -> Result<Uuid, AnyError> {
+) -> Result<Uuid, BlobError> {
   let blob_store = state.borrow::<Arc<BlobStore>>();
   let part = blob_store
     .get_part(&id)
-    .ok_or_else(|| type_error("Blob part not found"))?;
+    .ok_or(BlobError::BlobPartNotFound)?;
 
   let SliceOptions { start, len } = options;
 
   let size = part.size();
   if start + len > size {
-    return Err(type_error(
-      "start + len can not be larger than blob part size",
-    ));
+    return Err(BlobError::SizeLargerThanBlobPart);
   }
 
   let sliced_part = SlicedBlobPart { part, start, len };
@@ -215,14 +223,14 @@ pub fn op_blob_slice_part(
 pub async fn op_blob_read_part(
   state: Rc<RefCell<OpState>>,
   #[serde] id: Uuid,
-) -> Result<ToJsBuffer, AnyError> {
+) -> Result<ToJsBuffer, BlobError> {
   let part = {
     let state = state.borrow();
     let blob_store = state.borrow::<Arc<BlobStore>>();
     blob_store.get_part(&id)
   }
-  .ok_or_else(|| type_error("Blob part not found"))?;
-  let buf = part.read().await?;
+  .ok_or(BlobError::BlobPartNotFound)?;
+  let buf = part.read().await;
   Ok(ToJsBuffer::from(buf.to_vec()))
 }
 
@@ -238,13 +246,13 @@ pub fn op_blob_create_object_url(
   state: &mut OpState,
   #[string] media_type: String,
   #[serde] part_ids: Vec<Uuid>,
-) -> Result<String, AnyError> {
+) -> Result<String, BlobError> {
   let mut parts = Vec::with_capacity(part_ids.len());
   let blob_store = state.borrow::<Arc<BlobStore>>();
   for part_id in part_ids {
     let part = blob_store
       .get_part(&part_id)
-      .ok_or_else(|| type_error("Blob part not found"))?;
+      .ok_or(BlobError::BlobPartNotFound)?;
     parts.push(part);
   }
 
@@ -263,7 +271,7 @@ pub fn op_blob_create_object_url(
 pub fn op_blob_revoke_object_url(
   state: &mut OpState,
   #[string] url: &str,
-) -> Result<(), AnyError> {
+) -> Result<(), BlobError> {
   let url = Url::parse(url)?;
   let blob_store = state.borrow::<Arc<BlobStore>>();
   blob_store.remove_object_url(&url);
@@ -287,15 +295,15 @@ pub struct ReturnBlobPart {
 pub fn op_blob_from_object_url(
   state: &mut OpState,
   #[string] url: String,
-) -> Result<Option<ReturnBlob>, AnyError> {
+) -> Result<Option<ReturnBlob>, BlobError> {
   let url = Url::parse(&url)?;
   if url.scheme() != "blob" {
     return Ok(None);
   }
 
-  let blob_store = state.try_borrow::<Arc<BlobStore>>().ok_or_else(|| {
-    type_error("Blob URLs are not supported in this context.")
-  })?;
+  let blob_store = state
+    .try_borrow::<Arc<BlobStore>>()
+    .ok_or(BlobError::BlobURLsNotSupported)?;
   if let Some(blob) = blob_store.get_object_url(url) {
     let parts = blob
       .parts
diff --git a/ext/web/compression.rs b/ext/web/compression.rs
index b9ae12ef17..6967009915 100644
--- a/ext/web/compression.rs
+++ b/ext/web/compression.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use flate2::write::DeflateDecoder;
 use flate2::write::DeflateEncoder;
@@ -13,6 +11,18 @@ use flate2::Compression;
 use std::cell::RefCell;
 use std::io::Write;
 
+#[derive(Debug, thiserror::Error)]
+pub enum CompressionError {
+  #[error("Unsupported format")]
+  UnsupportedFormat,
+  #[error("resource is closed")]
+  ResourceClosed,
+  #[error(transparent)]
+  IoTypeError(std::io::Error),
+  #[error(transparent)]
+  Io(std::io::Error),
+}
+
 #[derive(Debug)]
 struct CompressionResource(RefCell<Option<Inner>>);
 
@@ -34,7 +44,7 @@ enum Inner {
 pub fn op_compression_new(
   #[string] format: &str,
   is_decoder: bool,
-) -> Result<CompressionResource, AnyError> {
+) -> Result<CompressionResource, CompressionError> {
   let w = Vec::new();
   let inner = match (format, is_decoder) {
     ("deflate", true) => Inner::DeflateDecoder(ZlibDecoder::new(w)),
@@ -49,7 +59,7 @@ pub fn op_compression_new(
     ("gzip", false) => {
       Inner::GzEncoder(GzEncoder::new(w, Compression::default()))
     }
-    _ => return Err(type_error("Unsupported format")),
+    _ => return Err(CompressionError::UnsupportedFormat),
   };
   Ok(CompressionResource(RefCell::new(Some(inner))))
 }
@@ -59,40 +69,38 @@ pub fn op_compression_new(
 pub fn op_compression_write(
   #[cppgc] resource: &CompressionResource,
   #[anybuffer] input: &[u8],
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, CompressionError> {
   let mut inner = resource.0.borrow_mut();
-  let inner = inner
-    .as_mut()
-    .ok_or_else(|| type_error("resource is closed"))?;
+  let inner = inner.as_mut().ok_or(CompressionError::ResourceClosed)?;
   let out: Vec<u8> = match &mut *inner {
     Inner::DeflateDecoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::DeflateEncoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::DeflateRawDecoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::DeflateRawEncoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::GzDecoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
     Inner::GzEncoder(d) => {
-      d.write_all(input).map_err(|e| type_error(e.to_string()))?;
-      d.flush()?;
+      d.write_all(input).map_err(CompressionError::IoTypeError)?;
+      d.flush().map_err(CompressionError::Io)?;
       d.get_mut().drain(..)
     }
   }
@@ -105,27 +113,27 @@ pub fn op_compression_write(
 pub fn op_compression_finish(
   #[cppgc] resource: &CompressionResource,
   report_errors: bool,
-) -> Result<Vec<u8>, AnyError> {
+) -> Result<Vec<u8>, CompressionError> {
   let inner = resource
     .0
     .borrow_mut()
     .take()
-    .ok_or_else(|| type_error("resource is closed"))?;
+    .ok_or(CompressionError::ResourceClosed)?;
   let out = match inner {
     Inner::DeflateDecoder(d) => {
-      d.finish().map_err(|e| type_error(e.to_string()))
+      d.finish().map_err(CompressionError::IoTypeError)
     }
     Inner::DeflateEncoder(d) => {
-      d.finish().map_err(|e| type_error(e.to_string()))
+      d.finish().map_err(CompressionError::IoTypeError)
     }
     Inner::DeflateRawDecoder(d) => {
-      d.finish().map_err(|e| type_error(e.to_string()))
+      d.finish().map_err(CompressionError::IoTypeError)
     }
     Inner::DeflateRawEncoder(d) => {
-      d.finish().map_err(|e| type_error(e.to_string()))
+      d.finish().map_err(CompressionError::IoTypeError)
     }
-    Inner::GzDecoder(d) => d.finish().map_err(|e| type_error(e.to_string())),
-    Inner::GzEncoder(d) => d.finish().map_err(|e| type_error(e.to_string())),
+    Inner::GzDecoder(d) => d.finish().map_err(CompressionError::IoTypeError),
+    Inner::GzEncoder(d) => d.finish().map_err(CompressionError::IoTypeError),
   };
   match out {
     Err(err) => {
diff --git a/ext/web/lib.rs b/ext/web/lib.rs
index 3977379a5d..4935af5bd3 100644
--- a/ext/web/lib.rs
+++ b/ext/web/lib.rs
@@ -6,9 +6,6 @@ mod message_port;
 mod stream_resource;
 mod timers;
 
-use deno_core::error::range_error;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::url::Url;
 use deno_core::v8;
@@ -22,10 +19,14 @@ use encoding_rs::DecoderResult;
 use encoding_rs::Encoding;
 use std::borrow::Cow;
 use std::cell::RefCell;
-use std::fmt;
 use std::path::PathBuf;
 use std::sync::Arc;
 
+pub use blob::BlobError;
+pub use compression::CompressionError;
+pub use message_port::MessagePortError;
+pub use stream_resource::StreamResourceError;
+
 use crate::blob::op_blob_create_object_url;
 use crate::blob::op_blob_create_part;
 use crate::blob::op_blob_from_object_url;
@@ -126,9 +127,27 @@ deno_core::extension!(deno_web,
   }
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum WebError {
+  #[error("Failed to decode base64")]
+  Base64Decode,
+  #[error("The encoding label provided ('{0}') is invalid.")]
+  InvalidEncodingLabel(String),
+  #[error("buffer exceeds maximum length")]
+  BufferTooLong,
+  #[error("Value too large to decode")]
+  ValueTooLarge,
+  #[error("Provided buffer too small")]
+  BufferTooSmall,
+  #[error("The encoded data is not valid")]
+  DataInvalid,
+  #[error(transparent)]
+  DataError(#[from] v8::DataError),
+}
+
 #[op2]
 #[serde]
-fn op_base64_decode(#[string] input: String) -> Result<ToJsBuffer, AnyError> {
+fn op_base64_decode(#[string] input: String) -> Result<ToJsBuffer, WebError> {
   let mut s = input.into_bytes();
   let decoded_len = forgiving_base64_decode_inplace(&mut s)?;
   s.truncate(decoded_len);
@@ -137,7 +156,7 @@ fn op_base64_decode(#[string] input: String) -> Result<ToJsBuffer, AnyError> {
 
 #[op2]
 #[serde]
-fn op_base64_atob(#[serde] mut s: ByteString) -> Result<ByteString, AnyError> {
+fn op_base64_atob(#[serde] mut s: ByteString) -> Result<ByteString, WebError> {
   let decoded_len = forgiving_base64_decode_inplace(&mut s)?;
   s.truncate(decoded_len);
   Ok(s)
@@ -147,11 +166,9 @@ fn op_base64_atob(#[serde] mut s: ByteString) -> Result<ByteString, AnyError> {
 #[inline]
 fn forgiving_base64_decode_inplace(
   input: &mut [u8],
-) -> Result<usize, AnyError> {
-  let error =
-    || DomExceptionInvalidCharacterError::new("Failed to decode base64");
-  let decoded =
-    base64_simd::forgiving_decode_inplace(input).map_err(|_| error())?;
+) -> Result<usize, WebError> {
+  let decoded = base64_simd::forgiving_decode_inplace(input)
+    .map_err(|_| WebError::Base64Decode)?;
   Ok(decoded.len())
 }
 
@@ -177,13 +194,9 @@ fn forgiving_base64_encode(s: &[u8]) -> String {
 #[string]
 fn op_encoding_normalize_label(
   #[string] label: String,
-) -> Result<String, AnyError> {
+) -> Result<String, WebError> {
   let encoding = Encoding::for_label_no_replacement(label.as_bytes())
-    .ok_or_else(|| {
-      range_error(format!(
-        "The encoding label provided ('{label}') is invalid."
-      ))
-    })?;
+    .ok_or(WebError::InvalidEncodingLabel(label))?;
   Ok(encoding.name().to_lowercase())
 }
 
@@ -192,7 +205,7 @@ fn op_encoding_decode_utf8<'a>(
   scope: &mut v8::HandleScope<'a>,
   #[anybuffer] zero_copy: &[u8],
   ignore_bom: bool,
-) -> Result<v8::Local<'a, v8::String>, AnyError> {
+) -> Result<v8::Local<'a, v8::String>, WebError> {
   let buf = &zero_copy;
 
   let buf = if !ignore_bom
@@ -216,7 +229,7 @@ fn op_encoding_decode_utf8<'a>(
   // - https://github.com/v8/v8/blob/d68fb4733e39525f9ff0a9222107c02c28096e2a/include/v8.h#L3277-L3278
   match v8::String::new_from_utf8(scope, buf, v8::NewStringType::Normal) {
     Some(text) => Ok(text),
-    None => Err(type_error("buffer exceeds maximum length")),
+    None => Err(WebError::BufferTooLong),
   }
 }
 
@@ -227,12 +240,9 @@ fn op_encoding_decode_single(
   #[string] label: String,
   fatal: bool,
   ignore_bom: bool,
-) -> Result<U16String, AnyError> {
-  let encoding = Encoding::for_label(label.as_bytes()).ok_or_else(|| {
-    range_error(format!(
-      "The encoding label provided ('{label}') is invalid."
-    ))
-  })?;
+) -> Result<U16String, WebError> {
+  let encoding = Encoding::for_label(label.as_bytes())
+    .ok_or(WebError::InvalidEncodingLabel(label))?;
 
   let mut decoder = if ignore_bom {
     encoding.new_decoder_without_bom_handling()
@@ -242,7 +252,7 @@ fn op_encoding_decode_single(
 
   let max_buffer_length = decoder
     .max_utf16_buffer_length(data.len())
-    .ok_or_else(|| range_error("Value too large to decode."))?;
+    .ok_or(WebError::ValueTooLarge)?;
 
   let mut output = vec![0; max_buffer_length];
 
@@ -254,12 +264,8 @@ fn op_encoding_decode_single(
         output.truncate(written);
         Ok(output.into())
       }
-      DecoderResult::OutputFull => {
-        Err(range_error("Provided buffer too small."))
-      }
-      DecoderResult::Malformed(_, _) => {
-        Err(type_error("The encoded data is not valid."))
-      }
+      DecoderResult::OutputFull => Err(WebError::BufferTooSmall),
+      DecoderResult::Malformed(_, _) => Err(WebError::DataInvalid),
     }
   } else {
     let (result, _, written, _) =
@@ -269,7 +275,7 @@ fn op_encoding_decode_single(
         output.truncate(written);
         Ok(output.into())
       }
-      CoderResult::OutputFull => Err(range_error("Provided buffer too small.")),
+      CoderResult::OutputFull => Err(WebError::BufferTooSmall),
     }
   }
 }
@@ -280,12 +286,9 @@ fn op_encoding_new_decoder(
   #[string] label: &str,
   fatal: bool,
   ignore_bom: bool,
-) -> Result<TextDecoderResource, AnyError> {
-  let encoding = Encoding::for_label(label.as_bytes()).ok_or_else(|| {
-    range_error(format!(
-      "The encoding label provided ('{label}') is invalid."
-    ))
-  })?;
+) -> Result<TextDecoderResource, WebError> {
+  let encoding = Encoding::for_label(label.as_bytes())
+    .ok_or_else(|| WebError::InvalidEncodingLabel(label.to_string()))?;
 
   let decoder = if ignore_bom {
     encoding.new_decoder_without_bom_handling()
@@ -305,13 +308,13 @@ fn op_encoding_decode(
   #[anybuffer] data: &[u8],
   #[cppgc] resource: &TextDecoderResource,
   stream: bool,
-) -> Result<U16String, AnyError> {
+) -> Result<U16String, WebError> {
   let mut decoder = resource.decoder.borrow_mut();
   let fatal = resource.fatal;
 
   let max_buffer_length = decoder
     .max_utf16_buffer_length(data.len())
-    .ok_or_else(|| range_error("Value too large to decode."))?;
+    .ok_or(WebError::ValueTooLarge)?;
 
   let mut output = vec![0; max_buffer_length];
 
@@ -323,12 +326,8 @@ fn op_encoding_decode(
         output.truncate(written);
         Ok(output.into())
       }
-      DecoderResult::OutputFull => {
-        Err(range_error("Provided buffer too small."))
-      }
-      DecoderResult::Malformed(_, _) => {
-        Err(type_error("The encoded data is not valid."))
-      }
+      DecoderResult::OutputFull => Err(WebError::BufferTooSmall),
+      DecoderResult::Malformed(_, _) => Err(WebError::DataInvalid),
     }
   } else {
     let (result, _, written, _) =
@@ -338,7 +337,7 @@ fn op_encoding_decode(
         output.truncate(written);
         Ok(output.into())
       }
-      CoderResult::OutputFull => Err(range_error("Provided buffer too small.")),
+      CoderResult::OutputFull => Err(WebError::BufferTooSmall),
     }
   }
 }
@@ -356,7 +355,7 @@ fn op_encoding_encode_into(
   input: v8::Local<v8::Value>,
   #[buffer] buffer: &mut [u8],
   #[buffer] out_buf: &mut [u32],
-) -> Result<(), AnyError> {
+) -> Result<(), WebError> {
   let s = v8::Local::<v8::String>::try_from(input)?;
 
   let mut nchars = 0;
@@ -414,53 +413,4 @@ pub fn get_declaration() -> PathBuf {
   PathBuf::from(env!("CARGO_MANIFEST_DIR")).join("lib.deno_web.d.ts")
 }
 
-#[derive(Debug)]
-pub struct DomExceptionQuotaExceededError {
-  pub msg: String,
-}
-
-impl DomExceptionQuotaExceededError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionQuotaExceededError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-#[derive(Debug)]
-pub struct DomExceptionInvalidCharacterError {
-  pub msg: String,
-}
-
-impl DomExceptionInvalidCharacterError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionInvalidCharacterError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-impl fmt::Display for DomExceptionQuotaExceededError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-impl fmt::Display for DomExceptionInvalidCharacterError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-
-impl std::error::Error for DomExceptionQuotaExceededError {}
-
-impl std::error::Error for DomExceptionInvalidCharacterError {}
-
-pub fn get_error_class_name(e: &AnyError) -> Option<&'static str> {
-  e.downcast_ref::<DomExceptionQuotaExceededError>()
-    .map(|_| "DOMExceptionQuotaExceededError")
-    .or_else(|| {
-      e.downcast_ref::<DomExceptionInvalidCharacterError>()
-        .map(|_| "DOMExceptionInvalidCharacterError")
-    })
-}
 pub struct Location(pub Url);
diff --git a/ext/web/message_port.rs b/ext/web/message_port.rs
index fa299475d9..1a4a09073d 100644
--- a/ext/web/message_port.rs
+++ b/ext/web/message_port.rs
@@ -4,8 +4,6 @@ use std::borrow::Cow;
 use std::cell::RefCell;
 use std::rc::Rc;
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 
 use deno_core::CancelFuture;
@@ -23,6 +21,20 @@ use tokio::sync::mpsc::unbounded_channel;
 use tokio::sync::mpsc::UnboundedReceiver;
 use tokio::sync::mpsc::UnboundedSender;
 
+#[derive(Debug, thiserror::Error)]
+pub enum MessagePortError {
+  #[error("Invalid message port transfer")]
+  InvalidTransfer,
+  #[error("Message port is not ready for transfer")]
+  NotReady,
+  #[error("Can not transfer self message port")]
+  TransferSelf,
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+}
+
 pub enum Transferable {
   MessagePort(MessagePort),
   ArrayBuffer(u32),
@@ -40,7 +52,7 @@ impl MessagePort {
     &self,
     state: &mut OpState,
     data: JsMessageData,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), MessagePortError> {
     let transferables =
       deserialize_js_transferables(state, data.transferables)?;
 
@@ -56,7 +68,7 @@ impl MessagePort {
   pub async fn recv(
     &self,
     state: Rc<RefCell<OpState>>,
-  ) -> Result<Option<JsMessageData>, AnyError> {
+  ) -> Result<Option<JsMessageData>, MessagePortError> {
     let rx = &self.rx;
 
     let maybe_data = poll_fn(|cx| {
@@ -147,7 +159,7 @@ pub enum JsTransferable {
 pub fn deserialize_js_transferables(
   state: &mut OpState,
   js_transferables: Vec<JsTransferable>,
-) -> Result<Vec<Transferable>, AnyError> {
+) -> Result<Vec<Transferable>, MessagePortError> {
   let mut transferables = Vec::with_capacity(js_transferables.len());
   for js_transferable in js_transferables {
     match js_transferable {
@@ -155,10 +167,10 @@ pub fn deserialize_js_transferables(
         let resource = state
           .resource_table
           .take::<MessagePortResource>(id)
-          .map_err(|_| type_error("Invalid message port transfer"))?;
+          .map_err(|_| MessagePortError::InvalidTransfer)?;
         resource.cancel.cancel();
-        let resource = Rc::try_unwrap(resource)
-          .map_err(|_| type_error("Message port is not ready for transfer"))?;
+        let resource =
+          Rc::try_unwrap(resource).map_err(|_| MessagePortError::NotReady)?;
         transferables.push(Transferable::MessagePort(resource.port));
       }
       JsTransferable::ArrayBuffer(id) => {
@@ -202,16 +214,19 @@ pub fn op_message_port_post_message(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[serde] data: JsMessageData,
-) -> Result<(), AnyError> {
+) -> Result<(), MessagePortError> {
   for js_transferable in &data.transferables {
     if let JsTransferable::MessagePort(id) = js_transferable {
       if *id == rid {
-        return Err(type_error("Can not transfer self message port"));
+        return Err(MessagePortError::TransferSelf);
       }
     }
   }
 
-  let resource = state.resource_table.get::<MessagePortResource>(rid)?;
+  let resource = state
+    .resource_table
+    .get::<MessagePortResource>(rid)
+    .map_err(MessagePortError::Resource)?;
   resource.port.send(state, data)
 }
 
@@ -220,7 +235,7 @@ pub fn op_message_port_post_message(
 pub async fn op_message_port_recv_message(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<JsMessageData>, AnyError> {
+) -> Result<Option<JsMessageData>, MessagePortError> {
   let resource = {
     let state = state.borrow();
     match state.resource_table.get::<MessagePortResource>(rid) {
@@ -237,8 +252,11 @@ pub async fn op_message_port_recv_message(
 pub fn op_message_port_recv_message_sync(
   state: &mut OpState, // Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<JsMessageData>, AnyError> {
-  let resource = state.resource_table.get::<MessagePortResource>(rid)?;
+) -> Result<Option<JsMessageData>, MessagePortError> {
+  let resource = state
+    .resource_table
+    .get::<MessagePortResource>(rid)
+    .map_err(MessagePortError::Resource)?;
   let mut rx = resource.port.rx.borrow_mut();
 
   match rx.try_recv() {
diff --git a/ext/web/stream_resource.rs b/ext/web/stream_resource.rs
index 78487883b6..c44a385ea9 100644
--- a/ext/web/stream_resource.rs
+++ b/ext/web/stream_resource.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 use bytes::BytesMut;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::external;
 use deno_core::op2;
 use deno_core::serde_v8::V8Slice;
@@ -18,6 +16,7 @@ use deno_core::RcRef;
 use deno_core::Resource;
 use deno_core::ResourceId;
 use futures::future::poll_fn;
+use futures::TryFutureExt;
 use std::borrow::Cow;
 use std::cell::RefCell;
 use std::cell::RefMut;
@@ -31,6 +30,14 @@ use std::task::Context;
 use std::task::Poll;
 use std::task::Waker;
 
+#[derive(Debug, thiserror::Error)]
+pub enum StreamResourceError {
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+  #[error("{0}")]
+  Js(String),
+}
+
 // How many buffers we'll allow in the channel before we stop allowing writes.
 const BUFFER_CHANNEL_SIZE: u16 = 1024;
 
@@ -48,7 +55,7 @@ struct BoundedBufferChannelInner {
   buffers: [MaybeUninit<V8Slice<u8>>; BUFFER_CHANNEL_SIZE as _],
   ring_producer: u16,
   ring_consumer: u16,
-  error: Option<AnyError>,
+  error: Option<StreamResourceError>,
   current_size: usize,
   // TODO(mmastrac): we can math this field instead of accounting for it
   len: usize,
@@ -141,7 +148,10 @@ impl BoundedBufferChannelInner {
     self.len = 0;
   }
 
-  pub fn read(&mut self, limit: usize) -> Result<Option<BufView>, AnyError> {
+  pub fn read(
+    &mut self,
+    limit: usize,
+  ) -> Result<Option<BufView>, StreamResourceError> {
     // Empty buffers will return the error, if one exists, or None
     if self.len == 0 {
       if let Some(error) = self.error.take() {
@@ -230,7 +240,7 @@ impl BoundedBufferChannelInner {
     Ok(())
   }
 
-  pub fn write_error(&mut self, error: AnyError) {
+  pub fn write_error(&mut self, error: StreamResourceError) {
     self.error = Some(error);
     if let Some(waker) = self.read_waker.take() {
       waker.wake();
@@ -306,7 +316,10 @@ impl BoundedBufferChannel {
     self.inner.borrow_mut()
   }
 
-  pub fn read(&self, limit: usize) -> Result<Option<BufView>, AnyError> {
+  pub fn read(
+    &self,
+    limit: usize,
+  ) -> Result<Option<BufView>, StreamResourceError> {
     self.inner().read(limit)
   }
 
@@ -314,7 +327,7 @@ impl BoundedBufferChannel {
     self.inner().write(buffer)
   }
 
-  pub fn write_error(&self, error: AnyError) {
+  pub fn write_error(&self, error: StreamResourceError) {
     self.inner().write_error(error)
   }
 
@@ -358,7 +371,10 @@ impl ReadableStreamResource {
     RcRef::map(self, |s| &s.cancel_handle).clone()
   }
 
-  async fn read(self: Rc<Self>, limit: usize) -> Result<BufView, AnyError> {
+  async fn read(
+    self: Rc<Self>,
+    limit: usize,
+  ) -> Result<BufView, StreamResourceError> {
     let cancel_handle = self.cancel_handle();
     // Serialize all the reads using a task queue.
     let _read_permit = self.read_queue.acquire().await;
@@ -387,7 +403,7 @@ impl Resource for ReadableStreamResource {
   }
 
   fn read(self: Rc<Self>, limit: usize) -> AsyncResult<BufView> {
-    Box::pin(ReadableStreamResource::read(self, limit))
+    Box::pin(ReadableStreamResource::read(self, limit).map_err(|e| e.into()))
   }
 
   fn close(self: Rc<Self>) {
@@ -550,7 +566,7 @@ pub fn op_readable_stream_resource_write_error(
 ) -> bool {
   let sender = get_sender(sender);
   // We can always write an error, no polling required
-  sender.write_error(type_error(Cow::Owned(error)));
+  sender.write_error(StreamResourceError::Js(error));
   !sender.closed()
 }
 
diff --git a/ext/webgpu/Cargo.toml b/ext/webgpu/Cargo.toml
index 4c709b9c30..3bb814c25c 100644
--- a/ext/webgpu/Cargo.toml
+++ b/ext/webgpu/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_webgpu"
-version = "0.138.0"
+version = "0.142.0"
 authors = ["the Deno authors"]
 edition.workspace = true
 license = "MIT"
@@ -25,6 +25,7 @@ serde = { workspace = true, features = ["derive"] }
 tokio = { workspace = true, features = ["full"] }
 wgpu-types = { workspace = true, features = ["serde"] }
 raw-window-handle = { workspace = true }
+thiserror.workspace = true
 
 [target.'cfg(not(target_arch = "wasm32"))'.dependencies.wgpu-core]
 workspace = true
diff --git a/ext/webgpu/buffer.rs b/ext/webgpu/buffer.rs
index c6cd6f0a74..c2b53890e0 100644
--- a/ext/webgpu/buffer.rs
+++ b/ext/webgpu/buffer.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -13,9 +11,18 @@ use std::sync::Arc;
 use std::sync::Mutex;
 use std::time::Duration;
 
-use super::error::DomExceptionOperationError;
 use super::error::WebGpuResult;
 
+#[derive(Debug, thiserror::Error)]
+pub enum BufferError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("usage is not valid")]
+  InvalidUsage,
+  #[error(transparent)]
+  Access(wgpu_core::resource::BufferAccessError),
+}
+
 pub(crate) struct WebGpuBuffer(
   pub(crate) super::Instance,
   pub(crate) wgpu_core::id::BufferId,
@@ -46,18 +53,19 @@ pub fn op_webgpu_create_buffer(
   #[number] size: u64,
   usage: u32,
   mapped_at_creation: bool,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BufferError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
-    .get::<super::WebGpuDevice>(device_rid)?;
+    .get::<super::WebGpuDevice>(device_rid)
+    .map_err(BufferError::Resource)?;
   let device = device_resource.1;
 
   let descriptor = wgpu_core::resource::BufferDescriptor {
     label: Some(label),
     size,
     usage: wgpu_types::BufferUsages::from_bits(usage)
-      .ok_or_else(|| type_error("usage is not valid"))?,
+      .ok_or(BufferError::InvalidUsage)?,
     mapped_at_creation,
   };
 
@@ -77,18 +85,21 @@ pub async fn op_webgpu_buffer_get_map_async(
   mode: u32,
   #[number] offset: u64,
   #[number] size: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BufferError> {
   let device;
   let done = Arc::new(Mutex::new(None));
   {
     let state_ = state.borrow();
     let instance = state_.borrow::<super::Instance>();
-    let buffer_resource =
-      state_.resource_table.get::<WebGpuBuffer>(buffer_rid)?;
+    let buffer_resource = state_
+      .resource_table
+      .get::<WebGpuBuffer>(buffer_rid)
+      .map_err(BufferError::Resource)?;
     let buffer = buffer_resource.1;
     let device_resource = state_
       .resource_table
-      .get::<super::WebGpuDevice>(device_rid)?;
+      .get::<super::WebGpuDevice>(device_rid)
+      .map_err(BufferError::Resource)?;
     device = device_resource.1;
 
     let done_ = done.clone();
@@ -120,9 +131,7 @@ pub async fn op_webgpu_buffer_get_map_async(
     let result = done.lock().unwrap().take();
     match result {
       Some(Ok(())) => return Ok(WebGpuResult::empty()),
-      Some(Err(e)) => {
-        return Err(DomExceptionOperationError::new(&e.to_string()).into())
-      }
+      Some(Err(e)) => return Err(BufferError::Access(e)),
       None => {
         {
           let state = state.borrow();
@@ -143,9 +152,12 @@ pub fn op_webgpu_buffer_get_mapped_range(
   #[number] offset: u64,
   #[number] size: Option<u64>,
   #[buffer] buf: &mut [u8],
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BufferError> {
   let instance = state.borrow::<super::Instance>();
-  let buffer_resource = state.resource_table.get::<WebGpuBuffer>(buffer_rid)?;
+  let buffer_resource = state
+    .resource_table
+    .get::<WebGpuBuffer>(buffer_rid)
+    .map_err(BufferError::Resource)?;
   let buffer = buffer_resource.1;
 
   let (slice_pointer, range_size) =
@@ -154,7 +166,7 @@ pub fn op_webgpu_buffer_get_mapped_range(
       offset,
       size
     ))
-    .map_err(|e| DomExceptionOperationError::new(&e.to_string()))?;
+    .map_err(BufferError::Access)?;
 
   // SAFETY: guarantee to be safe from wgpu
   let slice = unsafe {
@@ -176,12 +188,16 @@ pub fn op_webgpu_buffer_unmap(
   #[smi] buffer_rid: ResourceId,
   #[smi] mapped_rid: ResourceId,
   #[buffer] buf: Option<&[u8]>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BufferError> {
   let mapped_resource = state
     .resource_table
-    .take::<WebGpuBufferMapped>(mapped_rid)?;
+    .take::<WebGpuBufferMapped>(mapped_rid)
+    .map_err(BufferError::Resource)?;
   let instance = state.borrow::<super::Instance>();
-  let buffer_resource = state.resource_table.get::<WebGpuBuffer>(buffer_rid)?;
+  let buffer_resource = state
+    .resource_table
+    .get::<WebGpuBuffer>(buffer_rid)
+    .map_err(BufferError::Resource)?;
   let buffer = buffer_resource.1;
 
   if let Some(buf) = buf {
diff --git a/ext/webgpu/bundle.rs b/ext/webgpu/bundle.rs
index 57158271cc..d9a5b29539 100644
--- a/ext/webgpu/bundle.rs
+++ b/ext/webgpu/bundle.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -13,6 +11,14 @@ use std::rc::Rc;
 
 use super::error::WebGpuResult;
 
+#[derive(Debug, thiserror::Error)]
+pub enum BundleError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("size must be larger than 0")]
+  InvalidSize,
+}
+
 struct WebGpuRenderBundleEncoder(
   RefCell<wgpu_core::command::RenderBundleEncoder>,
 );
@@ -53,7 +59,7 @@ pub struct CreateRenderBundleEncoderArgs {
 pub fn op_webgpu_create_render_bundle_encoder(
   state: &mut OpState,
   #[serde] args: CreateRenderBundleEncoderArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let device_resource = state
     .resource_table
     .get::<super::WebGpuDevice>(args.device_rid)?;
@@ -100,7 +106,7 @@ pub fn op_webgpu_render_bundle_encoder_finish(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[string] label: Cow<str>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -131,7 +137,7 @@ pub fn op_webgpu_render_bundle_encoder_set_bind_group(
   #[buffer] dynamic_offsets_data: &[u32],
   #[number] dynamic_offsets_data_start: usize,
   #[number] dynamic_offsets_data_length: usize,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let bind_group_resource =
     state
       .resource_table
@@ -171,7 +177,7 @@ pub fn op_webgpu_render_bundle_encoder_push_debug_group(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[string] group_label: &str,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -195,7 +201,7 @@ pub fn op_webgpu_render_bundle_encoder_push_debug_group(
 pub fn op_webgpu_render_bundle_encoder_pop_debug_group(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -214,7 +220,7 @@ pub fn op_webgpu_render_bundle_encoder_insert_debug_marker(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[string] marker_label: &str,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -239,7 +245,7 @@ pub fn op_webgpu_render_bundle_encoder_set_pipeline(
   state: &mut OpState,
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[smi] pipeline: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pipeline_resource =
     state
       .resource_table
@@ -266,18 +272,17 @@ pub fn op_webgpu_render_bundle_encoder_set_index_buffer(
   #[serde] index_format: wgpu_types::IndexFormat,
   #[number] offset: u64,
   #[number] size: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BundleError> {
   let buffer_resource = state
     .resource_table
-    .get::<super::buffer::WebGpuBuffer>(buffer)?;
-  let render_bundle_encoder_resource =
-    state
-      .resource_table
-      .get::<WebGpuRenderBundleEncoder>(render_bundle_encoder_rid)?;
-  let size = Some(
-    std::num::NonZeroU64::new(size)
-      .ok_or_else(|| type_error("size must be larger than 0"))?,
-  );
+    .get::<super::buffer::WebGpuBuffer>(buffer)
+    .map_err(BundleError::Resource)?;
+  let render_bundle_encoder_resource = state
+    .resource_table
+    .get::<WebGpuRenderBundleEncoder>(render_bundle_encoder_rid)
+    .map_err(BundleError::Resource)?;
+  let size =
+    Some(std::num::NonZeroU64::new(size).ok_or(BundleError::InvalidSize)?);
 
   render_bundle_encoder_resource
     .0
@@ -296,19 +301,17 @@ pub fn op_webgpu_render_bundle_encoder_set_vertex_buffer(
   #[smi] buffer: ResourceId,
   #[number] offset: u64,
   #[number] size: Option<u64>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, BundleError> {
   let buffer_resource = state
     .resource_table
-    .get::<super::buffer::WebGpuBuffer>(buffer)?;
-  let render_bundle_encoder_resource =
-    state
-      .resource_table
-      .get::<WebGpuRenderBundleEncoder>(render_bundle_encoder_rid)?;
+    .get::<super::buffer::WebGpuBuffer>(buffer)
+    .map_err(BundleError::Resource)?;
+  let render_bundle_encoder_resource = state
+    .resource_table
+    .get::<WebGpuRenderBundleEncoder>(render_bundle_encoder_rid)
+    .map_err(BundleError::Resource)?;
   let size = if let Some(size) = size {
-    Some(
-      std::num::NonZeroU64::new(size)
-        .ok_or_else(|| type_error("size must be larger than 0"))?,
-    )
+    Some(std::num::NonZeroU64::new(size).ok_or(BundleError::InvalidSize)?)
   } else {
     None
   };
@@ -333,7 +336,7 @@ pub fn op_webgpu_render_bundle_encoder_draw(
   instance_count: u32,
   first_vertex: u32,
   first_instance: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -360,7 +363,7 @@ pub fn op_webgpu_render_bundle_encoder_draw_indexed(
   first_index: u32,
   base_vertex: i32,
   first_instance: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_bundle_encoder_resource =
     state
       .resource_table
@@ -385,7 +388,7 @@ pub fn op_webgpu_render_bundle_encoder_draw_indirect(
   #[smi] render_bundle_encoder_rid: ResourceId,
   #[smi] indirect_buffer: ResourceId,
   #[number] indirect_offset: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let buffer_resource = state
     .resource_table
     .get::<super::buffer::WebGpuBuffer>(indirect_buffer)?;
diff --git a/ext/webgpu/byow.rs b/ext/webgpu/byow.rs
index 3a43f416e5..c9e1177b1e 100644
--- a/ext/webgpu/byow.rs
+++ b/ext/webgpu/byow.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::ResourceId;
@@ -16,6 +14,47 @@ use std::ptr::NonNull;
 
 use crate::surface::WebGpuSurface;
 
+#[derive(Debug, thiserror::Error)]
+pub enum ByowError {
+  #[error("Cannot create surface outside of WebGPU context. Did you forget to call `navigator.gpu.requestAdapter()`?")]
+  WebGPUNotInitiated,
+  #[error("Invalid parameters")]
+  InvalidParameters,
+  #[error(transparent)]
+  CreateSurface(wgpu_core::instance::CreateSurfaceError),
+  #[cfg(target_os = "windows")]
+  #[error("Invalid system on Windows")]
+  InvalidSystem,
+  #[cfg(target_os = "macos")]
+  #[error("Invalid system on macOS")]
+  InvalidSystem,
+  #[cfg(any(
+    target_os = "linux",
+    target_os = "freebsd",
+    target_os = "openbsd"
+  ))]
+  #[error("Invalid system on Linux/BSD")]
+  InvalidSystem,
+  #[cfg(any(
+    target_os = "windows",
+    target_os = "linux",
+    target_os = "freebsd",
+    target_os = "openbsd"
+  ))]
+  #[error("window is null")]
+  NullWindow,
+  #[cfg(any(
+    target_os = "linux",
+    target_os = "freebsd",
+    target_os = "openbsd"
+  ))]
+  #[error("display is null")]
+  NullDisplay,
+  #[cfg(target_os = "macos")]
+  #[error("ns_view is null")]
+  NSViewDisplay,
+}
+
 #[op2(fast)]
 #[smi]
 pub fn op_webgpu_surface_create(
@@ -23,10 +62,10 @@ pub fn op_webgpu_surface_create(
   #[string] system: &str,
   p1: *const c_void,
   p2: *const c_void,
-) -> Result<ResourceId, AnyError> {
-  let instance = state.try_borrow::<super::Instance>().ok_or_else(|| {
-    type_error("Cannot create surface outside of WebGPU context. Did you forget to call `navigator.gpu.requestAdapter()`?")
-  })?;
+) -> Result<ResourceId, ByowError> {
+  let instance = state
+    .try_borrow::<super::Instance>()
+    .ok_or(ByowError::WebGPUNotInitiated)?;
   // Security note:
   //
   // The `p1` and `p2` parameters are pointers to platform-specific window
@@ -41,13 +80,15 @@ pub fn op_webgpu_surface_create(
   //
   // - Only FFI can export v8::External to user code.
   if p1.is_null() {
-    return Err(type_error("Invalid parameters"));
+    return Err(ByowError::InvalidParameters);
   }
 
   let (win_handle, display_handle) = raw_window(system, p1, p2)?;
   // SAFETY: see above comment
   let surface = unsafe {
-    instance.instance_create_surface(display_handle, win_handle, None)?
+    instance
+      .instance_create_surface(display_handle, win_handle, None)
+      .map_err(ByowError::CreateSurface)?
   };
 
   let rid = state
@@ -66,15 +107,14 @@ fn raw_window(
   system: &str,
   _ns_window: *const c_void,
   ns_view: *const c_void,
-) -> Result<RawHandles, AnyError> {
+) -> Result<RawHandles, ByowError> {
   if system != "cocoa" {
-    return Err(type_error("Invalid system on macOS"));
+    return Err(ByowError::InvalidSystem);
   }
 
   let win_handle = raw_window_handle::RawWindowHandle::AppKit(
     raw_window_handle::AppKitWindowHandle::new(
-      NonNull::new(ns_view as *mut c_void)
-        .ok_or(type_error("ns_view is null"))?,
+      NonNull::new(ns_view as *mut c_void).ok_or(ByowError::NSViewDisplay)?,
     ),
   );
 
@@ -89,16 +129,16 @@ fn raw_window(
   system: &str,
   window: *const c_void,
   hinstance: *const c_void,
-) -> Result<RawHandles, AnyError> {
+) -> Result<RawHandles, ByowError> {
   use raw_window_handle::WindowsDisplayHandle;
   if system != "win32" {
-    return Err(type_error("Invalid system on Windows"));
+    return Err(ByowError::InvalidSystem);
   }
 
   let win_handle = {
     let mut handle = raw_window_handle::Win32WindowHandle::new(
       std::num::NonZeroIsize::new(window as isize)
-        .ok_or(type_error("window is null"))?,
+        .ok_or(ByowError::NullWindow)?,
     );
     handle.hinstance = std::num::NonZeroIsize::new(hinstance as isize);
 
@@ -115,7 +155,7 @@ fn raw_window(
   system: &str,
   window: *const c_void,
   display: *const c_void,
-) -> Result<RawHandles, AnyError> {
+) -> Result<RawHandles, ByowError> {
   let (win_handle, display_handle);
   if system == "x11" {
     win_handle = raw_window_handle::RawWindowHandle::Xlib(
@@ -131,19 +171,17 @@ fn raw_window(
   } else if system == "wayland" {
     win_handle = raw_window_handle::RawWindowHandle::Wayland(
       raw_window_handle::WaylandWindowHandle::new(
-        NonNull::new(window as *mut c_void)
-          .ok_or(type_error("window is null"))?,
+        NonNull::new(window as *mut c_void).ok_or(ByowError::NullWindow)?,
       ),
     );
 
     display_handle = raw_window_handle::RawDisplayHandle::Wayland(
       raw_window_handle::WaylandDisplayHandle::new(
-        NonNull::new(display as *mut c_void)
-          .ok_or(type_error("display is null"))?,
+        NonNull::new(display as *mut c_void).ok_or(ByowError::NullDisplay)?,
       ),
     );
   } else {
-    return Err(type_error("Invalid system on Linux/BSD"));
+    return Err(ByowError::InvalidSystem);
   }
 
   Ok((win_handle, display_handle))
@@ -160,6 +198,6 @@ fn raw_window(
   _system: &str,
   _window: *const c_void,
   _display: *const c_void,
-) -> Result<RawHandles, AnyError> {
-  Err(type_error("Unsupported platform"))
+) -> Result<RawHandles, deno_core::error::AnyError> {
+  Err(deno_core::error::type_error("Unsupported platform"))
 }
diff --git a/ext/webgpu/error.rs b/ext/webgpu/error.rs
index 5b55d506ad..f08f765386 100644
--- a/ext/webgpu/error.rs
+++ b/ext/webgpu/error.rs
@@ -1,11 +1,9 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::ResourceId;
 use serde::Serialize;
 use std::convert::From;
 use std::error::Error;
-use std::fmt;
 use wgpu_core::binding_model::CreateBindGroupError;
 use wgpu_core::binding_model::CreateBindGroupLayoutError;
 use wgpu_core::binding_model::CreatePipelineLayoutError;
@@ -286,29 +284,3 @@ impl From<ConfigureSurfaceError> for WebGpuError {
     WebGpuError::Validation(fmt_err(&err))
   }
 }
-
-#[derive(Debug)]
-pub struct DomExceptionOperationError {
-  pub msg: String,
-}
-
-impl DomExceptionOperationError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionOperationError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-impl fmt::Display for DomExceptionOperationError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-
-impl std::error::Error for DomExceptionOperationError {}
-
-pub fn get_error_class_name(e: &AnyError) -> Option<&'static str> {
-  e.downcast_ref::<DomExceptionOperationError>()
-    .map(|_| "DOMExceptionOperationError")
-}
diff --git a/ext/webgpu/lib.rs b/ext/webgpu/lib.rs
index df2ab323af..5dc8278e41 100644
--- a/ext/webgpu/lib.rs
+++ b/ext/webgpu/lib.rs
@@ -2,7 +2,6 @@
 #![cfg(not(target_arch = "wasm32"))]
 #![warn(unsafe_op_in_unsafe_fn)]
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -16,7 +15,6 @@ use std::rc::Rc;
 pub use wgpu_core;
 pub use wgpu_types;
 
-use error::DomExceptionOperationError;
 use error::WebGpuResult;
 
 pub const UNSTABLE_FEATURE_NAME: &str = "webgpu";
@@ -44,7 +42,7 @@ mod macros {
         #[cfg(all(not(target_arch = "wasm32"), windows))]
         wgpu_types::Backend::Dx12 => $($c)*.$method::<wgpu_core::api::Dx12> $params,
         #[cfg(any(
-            all(unix, not(target_os = "macos"), not(target_os = "ios")),
+            all(not(target_os = "macos"), not(target_os = "ios")),
             feature = "angle",
             target_arch = "wasm32"
         ))]
@@ -85,6 +83,18 @@ pub mod shader;
 pub mod surface;
 pub mod texture;
 
+#[derive(Debug, thiserror::Error)]
+pub enum InitError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  InvalidAdapter(wgpu_core::instance::InvalidAdapter),
+  #[error(transparent)]
+  RequestDevice(wgpu_core::instance::RequestDeviceError),
+  #[error(transparent)]
+  InvalidDevice(wgpu_core::device::InvalidDevice),
+}
+
 pub type Instance = std::sync::Arc<wgpu_core::global::Global>;
 
 struct WebGpuAdapter(Instance, wgpu_core::id::AdapterId);
@@ -400,7 +410,7 @@ pub fn op_webgpu_request_adapter(
   state: Rc<RefCell<OpState>>,
   #[serde] power_preference: Option<wgpu_types::PowerPreference>,
   force_fallback_adapter: bool,
-) -> Result<GpuAdapterResOrErr, AnyError> {
+) -> Result<GpuAdapterResOrErr, InitError> {
   let mut state = state.borrow_mut();
 
   let backends = std::env::var("DENO_WEBGPU_BACKEND").map_or_else(
@@ -441,10 +451,11 @@ pub fn op_webgpu_request_adapter(
     }
   };
   let adapter_features =
-    gfx_select!(adapter => instance.adapter_features(adapter))?;
+    gfx_select!(adapter => instance.adapter_features(adapter))
+      .map_err(InitError::InvalidAdapter)?;
   let features = deserialize_features(&adapter_features);
-  let adapter_limits =
-    gfx_select!(adapter => instance.adapter_limits(adapter))?;
+  let adapter_limits = gfx_select!(adapter => instance.adapter_limits(adapter))
+    .map_err(InitError::InvalidAdapter)?;
 
   let instance = instance.clone();
 
@@ -663,10 +674,12 @@ pub fn op_webgpu_request_device(
   #[string] label: String,
   #[serde] required_features: GpuRequiredFeatures,
   #[serde] required_limits: Option<wgpu_types::Limits>,
-) -> Result<GpuDeviceRes, AnyError> {
+) -> Result<GpuDeviceRes, InitError> {
   let mut state = state.borrow_mut();
-  let adapter_resource =
-    state.resource_table.take::<WebGpuAdapter>(adapter_rid)?;
+  let adapter_resource = state
+    .resource_table
+    .take::<WebGpuAdapter>(adapter_rid)
+    .map_err(InitError::Resource)?;
   let adapter = adapter_resource.1;
   let instance = state.borrow::<Instance>();
 
@@ -685,13 +698,14 @@ pub fn op_webgpu_request_device(
   ));
   adapter_resource.close();
   if let Some(err) = maybe_err {
-    return Err(DomExceptionOperationError::new(&err.to_string()).into());
+    return Err(InitError::RequestDevice(err));
   }
 
-  let device_features =
-    gfx_select!(device => instance.device_features(device))?;
+  let device_features = gfx_select!(device => instance.device_features(device))
+    .map_err(InitError::InvalidDevice)?;
   let features = deserialize_features(&device_features);
-  let limits = gfx_select!(device => instance.device_limits(device))?;
+  let limits = gfx_select!(device => instance.device_limits(device))
+    .map_err(InitError::InvalidDevice)?;
 
   let instance = instance.clone();
   let instance2 = instance.clone();
@@ -722,14 +736,17 @@ pub struct GPUAdapterInfo {
 pub fn op_webgpu_request_adapter_info(
   state: Rc<RefCell<OpState>>,
   #[smi] adapter_rid: ResourceId,
-) -> Result<GPUAdapterInfo, AnyError> {
+) -> Result<GPUAdapterInfo, InitError> {
   let state = state.borrow_mut();
-  let adapter_resource =
-    state.resource_table.get::<WebGpuAdapter>(adapter_rid)?;
+  let adapter_resource = state
+    .resource_table
+    .get::<WebGpuAdapter>(adapter_rid)
+    .map_err(InitError::Resource)?;
   let adapter = adapter_resource.1;
   let instance = state.borrow::<Instance>();
 
-  let info = gfx_select!(adapter => instance.adapter_get_info(adapter))?;
+  let info = gfx_select!(adapter => instance.adapter_get_info(adapter))
+    .map_err(InitError::InvalidAdapter)?;
 
   Ok(GPUAdapterInfo {
     vendor: info.vendor.to_string(),
@@ -770,9 +787,11 @@ impl From<GpuQueryType> for wgpu_types::QueryType {
 pub fn op_webgpu_create_query_set(
   state: &mut OpState,
   #[serde] args: CreateQuerySetArgs,
-) -> Result<WebGpuResult, AnyError> {
-  let device_resource =
-    state.resource_table.get::<WebGpuDevice>(args.device_rid)?;
+) -> Result<WebGpuResult, InitError> {
+  let device_resource = state
+    .resource_table
+    .get::<WebGpuDevice>(args.device_rid)
+    .map_err(InitError::Resource)?;
   let device = device_resource.1;
   let instance = state.borrow::<Instance>();
 
diff --git a/ext/webgpu/render_pass.rs b/ext/webgpu/render_pass.rs
index c68be3d99a..9b9d87d9fc 100644
--- a/ext/webgpu/render_pass.rs
+++ b/ext/webgpu/render_pass.rs
@@ -1,7 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -12,6 +10,14 @@ use std::cell::RefCell;
 
 use super::error::WebGpuResult;
 
+#[derive(Debug, thiserror::Error)]
+pub enum RenderPassError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("size must be larger than 0")]
+  InvalidSize,
+}
+
 pub(crate) struct WebGpuRenderPass(
   pub(crate) RefCell<wgpu_core::command::RenderPass>,
 );
@@ -38,7 +44,7 @@ pub struct RenderPassSetViewportArgs {
 pub fn op_webgpu_render_pass_set_viewport(
   state: &mut OpState,
   #[serde] args: RenderPassSetViewportArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(args.render_pass_rid)?;
@@ -65,7 +71,7 @@ pub fn op_webgpu_render_pass_set_scissor_rect(
   y: u32,
   width: u32,
   height: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -87,7 +93,7 @@ pub fn op_webgpu_render_pass_set_blend_constant(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   #[serde] color: wgpu_types::Color,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -106,7 +112,7 @@ pub fn op_webgpu_render_pass_set_stencil_reference(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   reference: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -125,7 +131,7 @@ pub fn op_webgpu_render_pass_begin_occlusion_query(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   query_index: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -143,7 +149,7 @@ pub fn op_webgpu_render_pass_begin_occlusion_query(
 pub fn op_webgpu_render_pass_end_occlusion_query(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -161,7 +167,7 @@ pub fn op_webgpu_render_pass_execute_bundles(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   #[serde] bundles: Vec<u32>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let bundles = bundles
     .iter()
     .map(|rid| {
@@ -171,7 +177,7 @@ pub fn op_webgpu_render_pass_execute_bundles(
           .get::<super::bundle::WebGpuRenderBundle>(*rid)?;
       Ok(render_bundle_resource.1)
     })
-    .collect::<Result<Vec<_>, AnyError>>()?;
+    .collect::<Result<Vec<_>, deno_core::error::AnyError>>()?;
 
   let render_pass_resource = state
     .resource_table
@@ -191,7 +197,7 @@ pub fn op_webgpu_render_pass_end(
   state: &mut OpState,
   #[smi] command_encoder_rid: ResourceId,
   #[smi] render_pass_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let command_encoder_resource = state
     .resource_table
     .get::<super::command_encoder::WebGpuCommandEncoder>(
@@ -217,7 +223,7 @@ pub fn op_webgpu_render_pass_set_bind_group(
   #[buffer] dynamic_offsets_data: &[u32],
   #[number] dynamic_offsets_data_start: usize,
   #[number] dynamic_offsets_data_length: usize,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let bind_group_resource =
     state
       .resource_table
@@ -251,7 +257,7 @@ pub fn op_webgpu_render_pass_push_debug_group(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   #[string] group_label: &str,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -270,7 +276,7 @@ pub fn op_webgpu_render_pass_push_debug_group(
 pub fn op_webgpu_render_pass_pop_debug_group(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -288,7 +294,7 @@ pub fn op_webgpu_render_pass_insert_debug_marker(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   #[string] marker_label: &str,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -308,7 +314,7 @@ pub fn op_webgpu_render_pass_set_pipeline(
   state: &mut OpState,
   #[smi] render_pass_rid: ResourceId,
   pipeline: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pipeline_resource =
     state
       .resource_table
@@ -334,19 +340,18 @@ pub fn op_webgpu_render_pass_set_index_buffer(
   #[serde] index_format: wgpu_types::IndexFormat,
   #[number] offset: u64,
   #[number] size: Option<u64>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, RenderPassError> {
   let buffer_resource = state
     .resource_table
-    .get::<super::buffer::WebGpuBuffer>(buffer)?;
+    .get::<super::buffer::WebGpuBuffer>(buffer)
+    .map_err(RenderPassError::Resource)?;
   let render_pass_resource = state
     .resource_table
-    .get::<WebGpuRenderPass>(render_pass_rid)?;
+    .get::<WebGpuRenderPass>(render_pass_rid)
+    .map_err(RenderPassError::Resource)?;
 
   let size = if let Some(size) = size {
-    Some(
-      std::num::NonZeroU64::new(size)
-        .ok_or_else(|| type_error("size must be larger than 0"))?,
-    )
+    Some(std::num::NonZeroU64::new(size).ok_or(RenderPassError::InvalidSize)?)
   } else {
     None
   };
@@ -370,19 +375,18 @@ pub fn op_webgpu_render_pass_set_vertex_buffer(
   buffer: u32,
   #[number] offset: u64,
   #[number] size: Option<u64>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, RenderPassError> {
   let buffer_resource = state
     .resource_table
-    .get::<super::buffer::WebGpuBuffer>(buffer)?;
+    .get::<super::buffer::WebGpuBuffer>(buffer)
+    .map_err(RenderPassError::Resource)?;
   let render_pass_resource = state
     .resource_table
-    .get::<WebGpuRenderPass>(render_pass_rid)?;
+    .get::<WebGpuRenderPass>(render_pass_rid)
+    .map_err(RenderPassError::Resource)?;
 
   let size = if let Some(size) = size {
-    Some(
-      std::num::NonZeroU64::new(size)
-        .ok_or_else(|| type_error("size must be larger than 0"))?,
-    )
+    Some(std::num::NonZeroU64::new(size).ok_or(RenderPassError::InvalidSize)?)
   } else {
     None
   };
@@ -407,7 +411,7 @@ pub fn op_webgpu_render_pass_draw(
   instance_count: u32,
   first_vertex: u32,
   first_instance: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -433,7 +437,7 @@ pub fn op_webgpu_render_pass_draw_indexed(
   first_index: u32,
   base_vertex: i32,
   first_instance: u32,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let render_pass_resource = state
     .resource_table
     .get::<WebGpuRenderPass>(render_pass_rid)?;
@@ -457,7 +461,7 @@ pub fn op_webgpu_render_pass_draw_indirect(
   #[smi] render_pass_rid: ResourceId,
   indirect_buffer: u32,
   #[number] indirect_offset: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let buffer_resource = state
     .resource_table
     .get::<super::buffer::WebGpuBuffer>(indirect_buffer)?;
@@ -481,7 +485,7 @@ pub fn op_webgpu_render_pass_draw_indexed_indirect(
   #[smi] render_pass_rid: ResourceId,
   indirect_buffer: u32,
   #[number] indirect_offset: u64,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let buffer_resource = state
     .resource_table
     .get::<super::buffer::WebGpuBuffer>(indirect_buffer)?;
diff --git a/ext/webgpu/sampler.rs b/ext/webgpu/sampler.rs
index 27c36802e6..9fc1269ea7 100644
--- a/ext/webgpu/sampler.rs
+++ b/ext/webgpu/sampler.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -47,7 +46,7 @@ pub struct CreateSamplerArgs {
 pub fn op_webgpu_create_sampler(
   state: &mut OpState,
   #[serde] args: CreateSamplerArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
diff --git a/ext/webgpu/shader.rs b/ext/webgpu/shader.rs
index 0b3991c5de..4653bd85bf 100644
--- a/ext/webgpu/shader.rs
+++ b/ext/webgpu/shader.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -31,7 +30,7 @@ pub fn op_webgpu_create_shader_module(
   #[smi] device_rid: ResourceId,
   #[string] label: Cow<str>,
   #[string] code: Cow<str>,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
diff --git a/ext/webgpu/surface.rs b/ext/webgpu/surface.rs
index 1f6d2c87d2..297eaeb008 100644
--- a/ext/webgpu/surface.rs
+++ b/ext/webgpu/surface.rs
@@ -1,7 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
 use super::WebGpuResult;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -11,6 +10,16 @@ use std::borrow::Cow;
 use std::rc::Rc;
 use wgpu_types::SurfaceStatus;
 
+#[derive(Debug, thiserror::Error)]
+pub enum SurfaceError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("Invalid Surface Status")]
+  InvalidStatus,
+  #[error(transparent)]
+  Surface(wgpu_core::present::SurfaceError),
+}
+
 pub struct WebGpuSurface(pub crate::Instance, pub wgpu_core::id::SurfaceId);
 impl Resource for WebGpuSurface {
   fn name(&self) -> Cow<str> {
@@ -41,7 +50,7 @@ pub struct SurfaceConfigureArgs {
 pub fn op_webgpu_surface_configure(
   state: &mut OpState,
   #[serde] args: SurfaceConfigureArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
@@ -75,18 +84,22 @@ pub fn op_webgpu_surface_get_current_texture(
   state: &mut OpState,
   #[smi] device_rid: ResourceId,
   #[smi] surface_rid: ResourceId,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, SurfaceError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
-    .get::<super::WebGpuDevice>(device_rid)?;
+    .get::<super::WebGpuDevice>(device_rid)
+    .map_err(SurfaceError::Resource)?;
   let device = device_resource.1;
-  let surface_resource =
-    state.resource_table.get::<WebGpuSurface>(surface_rid)?;
+  let surface_resource = state
+    .resource_table
+    .get::<WebGpuSurface>(surface_rid)
+    .map_err(SurfaceError::Resource)?;
   let surface = surface_resource.1;
 
   let output =
-    gfx_select!(device => instance.surface_get_current_texture(surface, None))?;
+    gfx_select!(device => instance.surface_get_current_texture(surface, None))
+      .map_err(SurfaceError::Surface)?;
 
   match output.status {
     SurfaceStatus::Good | SurfaceStatus::Suboptimal => {
@@ -98,7 +111,7 @@ pub fn op_webgpu_surface_get_current_texture(
       });
       Ok(WebGpuResult::rid(rid))
     }
-    _ => Err(AnyError::msg("Invalid Surface Status")),
+    _ => Err(SurfaceError::InvalidStatus),
   }
 }
 
@@ -107,17 +120,21 @@ pub fn op_webgpu_surface_present(
   state: &mut OpState,
   #[smi] device_rid: ResourceId,
   #[smi] surface_rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), SurfaceError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
-    .get::<super::WebGpuDevice>(device_rid)?;
+    .get::<super::WebGpuDevice>(device_rid)
+    .map_err(SurfaceError::Resource)?;
   let device = device_resource.1;
-  let surface_resource =
-    state.resource_table.get::<WebGpuSurface>(surface_rid)?;
+  let surface_resource = state
+    .resource_table
+    .get::<WebGpuSurface>(surface_rid)
+    .map_err(SurfaceError::Resource)?;
   let surface = surface_resource.1;
 
-  let _ = gfx_select!(device => instance.surface_present(surface))?;
+  let _ = gfx_select!(device => instance.surface_present(surface))
+    .map_err(SurfaceError::Surface)?;
 
   Ok(())
 }
diff --git a/ext/webgpu/texture.rs b/ext/webgpu/texture.rs
index 44edd1a887..f8a5e05a3e 100644
--- a/ext/webgpu/texture.rs
+++ b/ext/webgpu/texture.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::Resource;
@@ -62,7 +61,7 @@ pub struct CreateTextureArgs {
 pub fn op_webgpu_create_texture(
   state: &mut OpState,
   #[serde] args: CreateTextureArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let device_resource = state
     .resource_table
@@ -111,7 +110,7 @@ pub struct CreateTextureViewArgs {
 pub fn op_webgpu_create_texture_view(
   state: &mut OpState,
   #[serde] args: CreateTextureViewArgs,
-) -> Result<WebGpuResult, AnyError> {
+) -> Result<WebGpuResult, deno_core::error::AnyError> {
   let instance = state.borrow::<super::Instance>();
   let texture_resource = state
     .resource_table
diff --git a/ext/webidl/Cargo.toml b/ext/webidl/Cargo.toml
index 8a25be3662..1685bb1fd0 100644
--- a/ext/webidl/Cargo.toml
+++ b/ext/webidl/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_webidl"
-version = "0.171.0"
+version = "0.175.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/ext/websocket/Cargo.toml b/ext/websocket/Cargo.toml
index 6bef387b44..6a575cb416 100644
--- a/ext/websocket/Cargo.toml
+++ b/ext/websocket/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_websocket"
-version = "0.176.0"
+version = "0.180.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -28,4 +28,5 @@ hyper-util.workspace = true
 once_cell.workspace = true
 rustls-tokio-stream.workspace = true
 serde.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
diff --git a/ext/websocket/lib.rs b/ext/websocket/lib.rs
index 9e320040b9..2a67ac5a17 100644
--- a/ext/websocket/lib.rs
+++ b/ext/websocket/lib.rs
@@ -1,10 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 use crate::stream::WebSocketStream;
 use bytes::Bytes;
-use deno_core::anyhow::bail;
-use deno_core::error::invalid_hostname;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::TryFutureExt;
 use deno_core::op2;
 use deno_core::unsync::spawn;
@@ -43,7 +39,6 @@ use serde::Serialize;
 use std::borrow::Cow;
 use std::cell::Cell;
 use std::cell::RefCell;
-use std::fmt;
 use std::future::Future;
 use std::num::NonZeroUsize;
 use std::path::PathBuf;
@@ -75,11 +70,33 @@ static USE_WRITEV: Lazy<bool> = Lazy::new(|| {
   false
 });
 
+#[derive(Debug, thiserror::Error)]
+pub enum WebsocketError {
+  #[error(transparent)]
+  Url(url::ParseError),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Uri(#[from] http::uri::InvalidUri),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error(transparent)]
+  WebSocket(#[from] fastwebsockets::WebSocketError),
+  #[error("failed to connect to WebSocket: {0}")]
+  ConnectionFailed(#[from] HandshakeError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+}
+
 #[derive(Clone)]
 pub struct WsRootStoreProvider(Option<Arc<dyn RootCertStoreProvider>>);
 
 impl WsRootStoreProvider {
-  pub fn get_or_try_init(&self) -> Result<Option<RootCertStore>, AnyError> {
+  pub fn get_or_try_init(
+    &self,
+  ) -> Result<Option<RootCertStore>, deno_core::error::AnyError> {
     Ok(match &self.0 {
       Some(provider) => Some(provider.get_or_try_init()?.clone()),
       None => None,
@@ -95,7 +112,7 @@ pub trait WebSocketPermissions {
     &mut self,
     _url: &url::Url,
     _api_name: &str,
-  ) -> Result<(), AnyError>;
+  ) -> Result<(), deno_core::error::AnyError>;
 }
 
 impl WebSocketPermissions for deno_permissions::PermissionsContainer {
@@ -104,7 +121,7 @@ impl WebSocketPermissions for deno_permissions::PermissionsContainer {
     &mut self,
     url: &url::Url,
     api_name: &str,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), deno_core::error::AnyError> {
     deno_permissions::PermissionsContainer::check_net_url(self, url, api_name)
   }
 }
@@ -137,13 +154,17 @@ pub fn op_ws_check_permission_and_cancel_handle<WP>(
   #[string] api_name: String,
   #[string] url: String,
   cancel_handle: bool,
-) -> Result<Option<ResourceId>, AnyError>
+) -> Result<Option<ResourceId>, WebsocketError>
 where
   WP: WebSocketPermissions + 'static,
 {
   state
     .borrow_mut::<WP>()
-    .check_net_url(&url::Url::parse(&url)?, &api_name)?;
+    .check_net_url(
+      &url::Url::parse(&url).map_err(WebsocketError::Url)?,
+      &api_name,
+    )
+    .map_err(WebsocketError::Permission)?;
 
   if cancel_handle {
     let rid = state
@@ -163,16 +184,46 @@ pub struct CreateResponse {
   extensions: String,
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum HandshakeError {
+  #[error("Missing path in url")]
+  MissingPath,
+  #[error("Invalid status code {0}")]
+  InvalidStatusCode(StatusCode),
+  #[error(transparent)]
+  Http(#[from] http::Error),
+  #[error(transparent)]
+  WebSocket(#[from] fastwebsockets::WebSocketError),
+  #[error("Didn't receive h2 alpn, aborting connection")]
+  NoH2Alpn,
+  #[error(transparent)]
+  Rustls(#[from] deno_tls::rustls::Error),
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  #[error(transparent)]
+  H2(#[from] h2::Error),
+  #[error("Invalid hostname: '{0}'")]
+  InvalidHostname(String),
+  #[error(transparent)]
+  RootStoreError(deno_core::error::AnyError),
+  #[error(transparent)]
+  Tls(deno_tls::TlsError),
+  #[error(transparent)]
+  HeaderName(#[from] http::header::InvalidHeaderName),
+  #[error(transparent)]
+  HeaderValue(#[from] http::header::InvalidHeaderValue),
+}
+
 async fn handshake_websocket(
   state: &Rc<RefCell<OpState>>,
   uri: &Uri,
   protocols: &str,
   headers: Option<Vec<(ByteString, ByteString)>>,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let mut request = Request::builder().method(Method::GET).uri(
     uri
       .path_and_query()
-      .ok_or(type_error("Missing path in url".to_string()))?
+      .ok_or(HandshakeError::MissingPath)?
       .as_str(),
   );
 
@@ -194,7 +245,9 @@ async fn handshake_websocket(
   request =
     populate_common_request_headers(request, &user_agent, protocols, &headers)?;
 
-  let request = request.body(http_body_util::Empty::new())?;
+  let request = request
+    .body(http_body_util::Empty::new())
+    .map_err(HandshakeError::Http)?;
   let domain = &uri.host().unwrap().to_string();
   let port = &uri.port_u16().unwrap_or(match uri.scheme_str() {
     Some("wss") => 443,
@@ -231,7 +284,7 @@ async fn handshake_websocket(
 async fn handshake_http1_ws(
   request: Request<http_body_util::Empty<Bytes>>,
   addr: &String,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let tcp_socket = TcpStream::connect(addr).await?;
   handshake_connection(request, tcp_socket).await
 }
@@ -241,11 +294,11 @@ async fn handshake_http1_wss(
   request: Request<http_body_util::Empty<Bytes>>,
   domain: &str,
   addr: &str,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let tcp_socket = TcpStream::connect(addr).await?;
   let tls_config = create_ws_client_config(state, SocketUse::Http1Only)?;
   let dnsname = ServerName::try_from(domain.to_string())
-    .map_err(|_| invalid_hostname(domain))?;
+    .map_err(|_| HandshakeError::InvalidHostname(domain.to_string()))?;
   let mut tls_connector = TlsStream::new_client_side(
     tcp_socket,
     ClientConnection::new(tls_config.into(), dnsname)?,
@@ -266,11 +319,11 @@ async fn handshake_http2_wss(
   domain: &str,
   headers: &Option<Vec<(ByteString, ByteString)>>,
   addr: &str,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let tcp_socket = TcpStream::connect(addr).await?;
   let tls_config = create_ws_client_config(state, SocketUse::Http2Only)?;
   let dnsname = ServerName::try_from(domain.to_string())
-    .map_err(|_| invalid_hostname(domain))?;
+    .map_err(|_| HandshakeError::InvalidHostname(domain.to_string()))?;
   // We need to better expose the underlying errors here
   let mut tls_connector = TlsStream::new_client_side(
     tcp_socket,
@@ -279,7 +332,7 @@ async fn handshake_http2_wss(
   );
   let handshake = tls_connector.handshake().await?;
   if handshake.alpn.is_none() {
-    bail!("Didn't receive h2 alpn, aborting connection");
+    return Err(HandshakeError::NoH2Alpn);
   }
   let h2 = h2::client::Builder::new();
   let (mut send, conn) = h2.handshake::<_, Bytes>(tls_connector).await?;
@@ -298,7 +351,7 @@ async fn handshake_http2_wss(
   let (resp, send) = send.send_request(request.body(())?, false)?;
   let resp = resp.await?;
   if resp.status() != StatusCode::OK {
-    bail!("Invalid status code: {}", resp.status());
+    return Err(HandshakeError::InvalidStatusCode(resp.status()));
   }
   let (http::response::Parts { headers, .. }, recv) = resp.into_parts();
   let mut stream = WebSocket::after_handshake(
@@ -317,7 +370,7 @@ async fn handshake_connection<
 >(
   request: Request<http_body_util::Empty<Bytes>>,
   socket: S,
-) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), AnyError> {
+) -> Result<(WebSocket<WebSocketStream>, http::HeaderMap), HandshakeError> {
   let (upgraded, response) =
     fastwebsockets::handshake::client(&LocalExecutor, request, socket).await?;
 
@@ -332,7 +385,7 @@ async fn handshake_connection<
 pub fn create_ws_client_config(
   state: &Rc<RefCell<OpState>>,
   socket_use: SocketUse,
-) -> Result<ClientConfig, AnyError> {
+) -> Result<ClientConfig, HandshakeError> {
   let unsafely_ignore_certificate_errors: Option<Vec<String>> = state
     .borrow()
     .try_borrow::<UnsafelyIgnoreCertificateErrors>()
@@ -340,7 +393,8 @@ pub fn create_ws_client_config(
   let root_cert_store = state
     .borrow()
     .borrow::<WsRootStoreProvider>()
-    .get_or_try_init()?;
+    .get_or_try_init()
+    .map_err(HandshakeError::RootStoreError)?;
 
   create_client_config(
     root_cert_store,
@@ -349,6 +403,7 @@ pub fn create_ws_client_config(
     TlsKeys::Null,
     socket_use,
   )
+  .map_err(HandshakeError::Tls)
 }
 
 /// Headers common to both http/1.1 and h2 requests.
@@ -357,7 +412,7 @@ fn populate_common_request_headers(
   user_agent: &str,
   protocols: &str,
   headers: &Option<Vec<(ByteString, ByteString)>>,
-) -> Result<http::request::Builder, AnyError> {
+) -> Result<http::request::Builder, HandshakeError> {
   request = request
     .header("User-Agent", user_agent)
     .header("Sec-WebSocket-Version", "13");
@@ -368,10 +423,8 @@ fn populate_common_request_headers(
 
   if let Some(headers) = headers {
     for (key, value) in headers {
-      let name = HeaderName::from_bytes(key)
-        .map_err(|err| type_error(err.to_string()))?;
-      let v = HeaderValue::from_bytes(value)
-        .map_err(|err| type_error(err.to_string()))?;
+      let name = HeaderName::from_bytes(key)?;
+      let v = HeaderValue::from_bytes(value)?;
 
       let is_disallowed_header = matches!(
         name,
@@ -401,14 +454,17 @@ pub async fn op_ws_create<WP>(
   #[string] protocols: String,
   #[smi] cancel_handle: Option<ResourceId>,
   #[serde] headers: Option<Vec<(ByteString, ByteString)>>,
-) -> Result<CreateResponse, AnyError>
+) -> Result<CreateResponse, WebsocketError>
 where
   WP: WebSocketPermissions + 'static,
 {
   {
     let mut s = state.borrow_mut();
     s.borrow_mut::<WP>()
-      .check_net_url(&url::Url::parse(&url)?, &api_name)
+      .check_net_url(
+        &url::Url::parse(&url).map_err(WebsocketError::Url)?,
+        &api_name,
+      )
       .expect(
         "Permission check should have been done in op_ws_check_permission",
       );
@@ -418,7 +474,8 @@ where
     let r = state
       .borrow_mut()
       .resource_table
-      .get::<WsCancelResource>(cancel_rid)?;
+      .get::<WsCancelResource>(cancel_rid)
+      .map_err(WebsocketError::Resource)?;
     Some(r.0.clone())
   } else {
     None
@@ -427,15 +484,11 @@ where
   let uri: Uri = url.parse()?;
 
   let handshake = handshake_websocket(&state, &uri, &protocols, headers)
-    .map_err(|err| {
-      AnyError::from(DomExceptionNetworkError::new(&format!(
-        "failed to connect to WebSocket: {err}"
-      )))
-    });
+    .map_err(WebsocketError::ConnectionFailed);
   let (stream, response) = match cancel_resource {
-    Some(rc) => handshake.try_or_cancel(rc).await,
-    None => handshake.await,
-  }?;
+    Some(rc) => handshake.try_or_cancel(rc).await?,
+    None => handshake.await?,
+  };
 
   if let Some(cancel_rid) = cancel_handle {
     if let Ok(res) = state.borrow_mut().resource_table.take_any(cancel_rid) {
@@ -520,14 +573,12 @@ impl ServerWebSocket {
     self: &Rc<Self>,
     lock: AsyncMutFuture<WebSocketWrite<WriteHalf<WebSocketStream>>>,
     frame: Frame<'_>,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), WebsocketError> {
     let mut ws = lock.await;
     if ws.is_closed() {
       return Ok(());
     }
-    ws.write_frame(frame)
-      .await
-      .map_err(|err| type_error(err.to_string()))?;
+    ws.write_frame(frame).await?;
     Ok(())
   }
 }
@@ -542,7 +593,7 @@ pub fn ws_create_server_stream(
   state: &mut OpState,
   transport: NetworkStream,
   read_buf: Bytes,
-) -> Result<ResourceId, AnyError> {
+) -> ResourceId {
   let mut ws = WebSocket::after_handshake(
     WebSocketStream::new(
       stream::WsStreamKind::Network(transport),
@@ -554,8 +605,7 @@ pub fn ws_create_server_stream(
   ws.set_auto_close(true);
   ws.set_auto_pong(true);
 
-  let rid = state.resource_table.add(ServerWebSocket::new(ws));
-  Ok(rid)
+  state.resource_table.add(ServerWebSocket::new(ws))
 }
 
 fn send_binary(state: &mut OpState, rid: ResourceId, data: &[u8]) {
@@ -625,11 +675,12 @@ pub async fn op_ws_send_binary_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[buffer] data: JsBuffer,
-) -> Result<(), AnyError> {
+) -> Result<(), WebsocketError> {
   let resource = state
     .borrow_mut()
     .resource_table
-    .get::<ServerWebSocket>(rid)?;
+    .get::<ServerWebSocket>(rid)
+    .map_err(WebsocketError::Resource)?;
   let data = data.to_vec();
   let lock = resource.reserve_lock();
   resource
@@ -643,11 +694,12 @@ pub async fn op_ws_send_text_async(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
   #[string] data: String,
-) -> Result<(), AnyError> {
+) -> Result<(), WebsocketError> {
   let resource = state
     .borrow_mut()
     .resource_table
-    .get::<ServerWebSocket>(rid)?;
+    .get::<ServerWebSocket>(rid)
+    .map_err(WebsocketError::Resource)?;
   let lock = resource.reserve_lock();
   resource
     .write_frame(
@@ -677,11 +729,12 @@ pub fn op_ws_get_buffered_amount(
 pub async fn op_ws_send_ping(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), WebsocketError> {
   let resource = state
     .borrow_mut()
     .resource_table
-    .get::<ServerWebSocket>(rid)?;
+    .get::<ServerWebSocket>(rid)
+    .map_err(WebsocketError::Resource)?;
   let lock = resource.reserve_lock();
   resource
     .write_frame(
@@ -697,7 +750,7 @@ pub async fn op_ws_close(
   #[smi] rid: ResourceId,
   #[smi] code: Option<u16>,
   #[string] reason: Option<String>,
-) -> Result<(), AnyError> {
+) -> Result<(), WebsocketError> {
   let Ok(resource) = state
     .borrow_mut()
     .resource_table
@@ -712,8 +765,7 @@ pub async fn op_ws_close(
 
   resource.closed.set(true);
   let lock = resource.reserve_lock();
-  resource.write_frame(lock, frame).await?;
-  Ok(())
+  resource.write_frame(lock, frame).await
 }
 
 #[op2]
@@ -867,32 +919,6 @@ pub fn get_declaration() -> PathBuf {
   PathBuf::from(env!("CARGO_MANIFEST_DIR")).join("lib.deno_websocket.d.ts")
 }
 
-#[derive(Debug)]
-pub struct DomExceptionNetworkError {
-  pub msg: String,
-}
-
-impl DomExceptionNetworkError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionNetworkError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-impl fmt::Display for DomExceptionNetworkError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-
-impl std::error::Error for DomExceptionNetworkError {}
-
-pub fn get_network_error_class_name(e: &AnyError) -> Option<&'static str> {
-  e.downcast_ref::<DomExceptionNetworkError>()
-    .map(|_| "DOMExceptionNetworkError")
-}
-
 // Needed so hyper can use non Send futures
 #[derive(Clone)]
 struct LocalExecutor;
diff --git a/ext/webstorage/Cargo.toml b/ext/webstorage/Cargo.toml
index 08ed8b0f29..079ab2e4ee 100644
--- a/ext/webstorage/Cargo.toml
+++ b/ext/webstorage/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_webstorage"
-version = "0.166.0"
+version = "0.170.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -17,3 +17,4 @@ path = "lib.rs"
 deno_core.workspace = true
 deno_web.workspace = true
 rusqlite.workspace = true
+thiserror.workspace = true
diff --git a/ext/webstorage/lib.rs b/ext/webstorage/lib.rs
index 99e61a1804..40946f05a7 100644
--- a/ext/webstorage/lib.rs
+++ b/ext/webstorage/lib.rs
@@ -2,10 +2,8 @@
 
 // NOTE to all: use **cached** prepared statements when interfacing with SQLite.
 
-use std::fmt;
 use std::path::PathBuf;
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use rusqlite::params;
@@ -14,6 +12,18 @@ use rusqlite::OptionalExtension;
 
 pub use rusqlite;
 
+#[derive(Debug, thiserror::Error)]
+pub enum WebStorageError {
+  #[error("LocalStorage is not supported in this context.")]
+  ContextNotSupported,
+  #[error(transparent)]
+  Sqlite(#[from] rusqlite::Error),
+  #[error(transparent)]
+  Io(std::io::Error),
+  #[error("Exceeded maximum storage size")]
+  StorageExceeded,
+}
+
 #[derive(Clone)]
 struct OriginStorageDir(PathBuf);
 
@@ -51,15 +61,13 @@ struct SessionStorage(Connection);
 fn get_webstorage(
   state: &mut OpState,
   persistent: bool,
-) -> Result<&Connection, AnyError> {
+) -> Result<&Connection, WebStorageError> {
   let conn = if persistent {
     if state.try_borrow::<LocalStorage>().is_none() {
-      let path = state.try_borrow::<OriginStorageDir>().ok_or_else(|| {
-        DomExceptionNotSupportedError::new(
-          "LocalStorage is not supported in this context.",
-        )
-      })?;
-      std::fs::create_dir_all(&path.0)?;
+      let path = state
+        .try_borrow::<OriginStorageDir>()
+        .ok_or(WebStorageError::ContextNotSupported)?;
+      std::fs::create_dir_all(&path.0).map_err(WebStorageError::Io)?;
       let conn = Connection::open(path.0.join("local_storage"))?;
       // Enable write-ahead-logging and tweak some other stuff.
       let initial_pragmas = "
@@ -106,7 +114,7 @@ fn get_webstorage(
 pub fn op_webstorage_length(
   state: &mut OpState,
   persistent: bool,
-) -> Result<u32, AnyError> {
+) -> Result<u32, WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("SELECT COUNT(*) FROM data")?;
@@ -121,7 +129,7 @@ pub fn op_webstorage_key(
   state: &mut OpState,
   #[smi] index: u32,
   persistent: bool,
-) -> Result<Option<String>, AnyError> {
+) -> Result<Option<String>, WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt =
@@ -135,14 +143,9 @@ pub fn op_webstorage_key(
 }
 
 #[inline]
-fn size_check(input: usize) -> Result<(), AnyError> {
+fn size_check(input: usize) -> Result<(), WebStorageError> {
   if input >= MAX_STORAGE_BYTES {
-    return Err(
-      deno_web::DomExceptionQuotaExceededError::new(
-        "Exceeded maximum storage size",
-      )
-      .into(),
-    );
+    return Err(WebStorageError::StorageExceeded);
   }
 
   Ok(())
@@ -154,7 +157,7 @@ pub fn op_webstorage_set(
   #[string] key: &str,
   #[string] value: &str,
   persistent: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   size_check(key.len() + value.len())?;
@@ -178,7 +181,7 @@ pub fn op_webstorage_get(
   state: &mut OpState,
   #[string] key_name: String,
   persistent: bool,
-) -> Result<Option<String>, AnyError> {
+) -> Result<Option<String>, WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("SELECT value FROM data WHERE key = ?")?;
@@ -194,7 +197,7 @@ pub fn op_webstorage_remove(
   state: &mut OpState,
   #[string] key_name: &str,
   persistent: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("DELETE FROM data WHERE key = ?")?;
@@ -207,7 +210,7 @@ pub fn op_webstorage_remove(
 pub fn op_webstorage_clear(
   state: &mut OpState,
   persistent: bool,
-) -> Result<(), AnyError> {
+) -> Result<(), WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("DELETE FROM data")?;
@@ -221,7 +224,7 @@ pub fn op_webstorage_clear(
 pub fn op_webstorage_iterate_keys(
   state: &mut OpState,
   persistent: bool,
-) -> Result<Vec<String>, AnyError> {
+) -> Result<Vec<String>, WebStorageError> {
   let conn = get_webstorage(state, persistent)?;
 
   let mut stmt = conn.prepare_cached("SELECT key FROM data")?;
@@ -232,31 +235,3 @@ pub fn op_webstorage_iterate_keys(
 
   Ok(keys)
 }
-
-#[derive(Debug)]
-pub struct DomExceptionNotSupportedError {
-  pub msg: String,
-}
-
-impl DomExceptionNotSupportedError {
-  pub fn new(msg: &str) -> Self {
-    DomExceptionNotSupportedError {
-      msg: msg.to_string(),
-    }
-  }
-}
-
-impl fmt::Display for DomExceptionNotSupportedError {
-  fn fmt(&self, f: &mut fmt::Formatter) -> fmt::Result {
-    f.pad(&self.msg)
-  }
-}
-
-impl std::error::Error for DomExceptionNotSupportedError {}
-
-pub fn get_not_supported_error_class_name(
-  e: &AnyError,
-) -> Option<&'static str> {
-  e.downcast_ref::<DomExceptionNotSupportedError>()
-    .map(|_| "DOMExceptionNotSupportedError")
-}
diff --git a/resolvers/deno/Cargo.toml b/resolvers/deno/Cargo.toml
index 62504c8303..d8569d7219 100644
--- a/resolvers/deno/Cargo.toml
+++ b/resolvers/deno/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_resolver"
-version = "0.3.0"
+version = "0.7.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/resolvers/deno/fs.rs b/resolvers/deno/fs.rs
index b08be37982..44495fa7c2 100644
--- a/resolvers/deno/fs.rs
+++ b/resolvers/deno/fs.rs
@@ -15,13 +15,3 @@ pub trait DenoResolverFs {
   fn is_dir_sync(&self, path: &Path) -> bool;
   fn read_dir_sync(&self, dir_path: &Path) -> std::io::Result<Vec<DirEntry>>;
 }
-
-pub(crate) struct DenoPkgJsonFsAdapter<'a, Fs: DenoResolverFs>(pub &'a Fs);
-
-impl<'a, Fs: DenoResolverFs> deno_package_json::fs::DenoPkgJsonFs
-  for DenoPkgJsonFsAdapter<'a, Fs>
-{
-  fn read_to_string_lossy(&self, path: &Path) -> std::io::Result<String> {
-    self.0.read_to_string_lossy(path)
-  }
-}
diff --git a/resolvers/deno/npm/byonm.rs b/resolvers/deno/npm/byonm.rs
index 3394b3e501..b85117052c 100644
--- a/resolvers/deno/npm/byonm.rs
+++ b/resolvers/deno/npm/byonm.rs
@@ -10,16 +10,17 @@ use deno_package_json::PackageJsonDepValue;
 use deno_path_util::url_to_file_path;
 use deno_semver::package::PackageReq;
 use deno_semver::Version;
+use node_resolver::env::NodeResolverEnv;
 use node_resolver::errors::PackageFolderResolveError;
 use node_resolver::errors::PackageFolderResolveIoError;
 use node_resolver::errors::PackageJsonLoadError;
 use node_resolver::errors::PackageNotFoundError;
-use node_resolver::load_pkg_json;
+use node_resolver::InNpmPackageChecker;
 use node_resolver::NpmResolver;
+use node_resolver::PackageJsonResolverRc;
 use thiserror::Error;
 use url::Url;
 
-use crate::fs::DenoPkgJsonFsAdapter;
 use crate::fs::DenoResolverFs;
 
 use super::local::normalize_pkg_name_for_node_modules_deno_folder;
@@ -36,32 +37,41 @@ pub enum ByonmResolvePkgFolderFromDenoReqError {
   Io(#[from] std::io::Error),
 }
 
-pub struct ByonmNpmResolverCreateOptions<Fs: DenoResolverFs> {
-  pub fs: Fs,
+pub struct ByonmNpmResolverCreateOptions<
+  Fs: DenoResolverFs,
+  TEnv: NodeResolverEnv,
+> {
   // todo(dsherret): investigate removing this
   pub root_node_modules_dir: Option<PathBuf>,
+  pub fs: Fs,
+  pub pkg_json_resolver: PackageJsonResolverRc<TEnv>,
 }
 
 #[derive(Debug)]
-pub struct ByonmNpmResolver<Fs: DenoResolverFs> {
+pub struct ByonmNpmResolver<Fs: DenoResolverFs, TEnv: NodeResolverEnv> {
   fs: Fs,
+  pkg_json_resolver: PackageJsonResolverRc<TEnv>,
   root_node_modules_dir: Option<PathBuf>,
 }
 
-impl<Fs: DenoResolverFs + Clone> Clone for ByonmNpmResolver<Fs> {
+impl<Fs: DenoResolverFs + Clone, TEnv: NodeResolverEnv> Clone
+  for ByonmNpmResolver<Fs, TEnv>
+{
   fn clone(&self) -> Self {
     Self {
       fs: self.fs.clone(),
+      pkg_json_resolver: self.pkg_json_resolver.clone(),
       root_node_modules_dir: self.root_node_modules_dir.clone(),
     }
   }
 }
 
-impl<Fs: DenoResolverFs> ByonmNpmResolver<Fs> {
-  pub fn new(options: ByonmNpmResolverCreateOptions<Fs>) -> Self {
+impl<Fs: DenoResolverFs, TEnv: NodeResolverEnv> ByonmNpmResolver<Fs, TEnv> {
+  pub fn new(options: ByonmNpmResolverCreateOptions<Fs, TEnv>) -> Self {
     Self {
-      fs: options.fs,
       root_node_modules_dir: options.root_node_modules_dir,
+      fs: options.fs,
+      pkg_json_resolver: options.pkg_json_resolver,
     }
   }
 
@@ -73,7 +83,7 @@ impl<Fs: DenoResolverFs> ByonmNpmResolver<Fs> {
     &self,
     path: &Path,
   ) -> Result<Option<Arc<PackageJson>>, PackageJsonLoadError> {
-    load_pkg_json(&DenoPkgJsonFsAdapter(&self.fs), path)
+    self.pkg_json_resolver.load_package_json(path)
   }
 
   /// Finds the ancestor package.json that contains the specified dependency.
@@ -290,8 +300,10 @@ impl<Fs: DenoResolverFs> ByonmNpmResolver<Fs> {
   }
 }
 
-impl<Fs: DenoResolverFs + Send + Sync + std::fmt::Debug> NpmResolver
-  for ByonmNpmResolver<Fs>
+impl<
+    Fs: DenoResolverFs + Send + Sync + std::fmt::Debug,
+    TEnv: NodeResolverEnv,
+  > NpmResolver for ByonmNpmResolver<Fs, TEnv>
 {
   fn resolve_package_folder_from_package(
     &self,
@@ -342,7 +354,12 @@ impl<Fs: DenoResolverFs + Send + Sync + std::fmt::Debug> NpmResolver
       .into()
     })
   }
+}
 
+#[derive(Debug)]
+pub struct ByonmInNpmPackageChecker;
+
+impl InNpmPackageChecker for ByonmInNpmPackageChecker {
   fn in_npm_package(&self, specifier: &Url) -> bool {
     specifier.scheme() == "file"
       && specifier
diff --git a/resolvers/deno/npm/mod.rs b/resolvers/deno/npm/mod.rs
index 9d885cad31..45e2341c78 100644
--- a/resolvers/deno/npm/mod.rs
+++ b/resolvers/deno/npm/mod.rs
@@ -3,6 +3,7 @@
 mod byonm;
 mod local;
 
+pub use byonm::ByonmInNpmPackageChecker;
 pub use byonm::ByonmNpmResolver;
 pub use byonm::ByonmNpmResolverCreateOptions;
 pub use byonm::ByonmResolvePkgFolderFromDenoReqError;
diff --git a/resolvers/deno/sloppy_imports.rs b/resolvers/deno/sloppy_imports.rs
index e215e87686..7aba5b771a 100644
--- a/resolvers/deno/sloppy_imports.rs
+++ b/resolvers/deno/sloppy_imports.rs
@@ -232,7 +232,7 @@ impl<Fs: SloppyImportResolverFs> SloppyImportsResolver<Fs> {
             | MediaType::Tsx
             | MediaType::Json
             | MediaType::Wasm
-            | MediaType::TsBuildInfo
+            | MediaType::Css
             | MediaType::SourceMap => {
               return None;
             }
diff --git a/resolvers/node/Cargo.toml b/resolvers/node/Cargo.toml
index f05b209fdb..95f7eabad8 100644
--- a/resolvers/node/Cargo.toml
+++ b/resolvers/node/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "node_resolver"
-version = "0.10.0"
+version = "0.14.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/resolvers/node/analyze.rs b/resolvers/node/analyze.rs
index 009296006a..c7415933d7 100644
--- a/resolvers/node/analyze.rs
+++ b/resolvers/node/analyze.rs
@@ -19,18 +19,19 @@ use anyhow::Error as AnyError;
 use url::Url;
 
 use crate::env::NodeResolverEnv;
-use crate::package_json::load_pkg_json;
+use crate::npm::InNpmPackageCheckerRc;
 use crate::resolution::NodeResolverRc;
 use crate::NodeModuleKind;
 use crate::NodeResolutionMode;
 use crate::NpmResolverRc;
+use crate::PackageJsonResolverRc;
 use crate::PathClean;
 
 #[derive(Debug, Clone)]
-pub enum CjsAnalysis {
+pub enum CjsAnalysis<'a> {
   /// File was found to be an ES module and the translator should
   /// load the code as ESM.
-  Esm(String),
+  Esm(Cow<'a, str>),
   Cjs(CjsAnalysisExports),
 }
 
@@ -50,11 +51,11 @@ pub trait CjsCodeAnalyzer {
   /// already has it. If the source is needed by the implementation,
   /// then it can use the provided source, or otherwise load it if
   /// necessary.
-  async fn analyze_cjs(
+  async fn analyze_cjs<'a>(
     &self,
     specifier: &Url,
-    maybe_source: Option<String>,
-  ) -> Result<CjsAnalysis, AnyError>;
+    maybe_source: Option<Cow<'a, str>>,
+  ) -> Result<CjsAnalysis<'a>, AnyError>;
 }
 
 pub struct NodeCodeTranslator<
@@ -63,8 +64,10 @@ pub struct NodeCodeTranslator<
 > {
   cjs_code_analyzer: TCjsCodeAnalyzer,
   env: TNodeResolverEnv,
+  in_npm_pkg_checker: InNpmPackageCheckerRc,
   node_resolver: NodeResolverRc<TNodeResolverEnv>,
   npm_resolver: NpmResolverRc,
+  pkg_json_resolver: PackageJsonResolverRc<TNodeResolverEnv>,
 }
 
 impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
@@ -73,14 +76,18 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
   pub fn new(
     cjs_code_analyzer: TCjsCodeAnalyzer,
     env: TNodeResolverEnv,
+    in_npm_pkg_checker: InNpmPackageCheckerRc,
     node_resolver: NodeResolverRc<TNodeResolverEnv>,
     npm_resolver: NpmResolverRc,
+    pkg_json_resolver: PackageJsonResolverRc<TNodeResolverEnv>,
   ) -> Self {
     Self {
       cjs_code_analyzer,
       env,
+      in_npm_pkg_checker,
       node_resolver,
       npm_resolver,
+      pkg_json_resolver,
     }
   }
 
@@ -90,11 +97,11 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
   /// For all discovered reexports the analysis will be performed recursively.
   ///
   /// If successful a source code for equivalent ES module is returned.
-  pub async fn translate_cjs_to_esm(
+  pub async fn translate_cjs_to_esm<'a>(
     &self,
     entry_specifier: &Url,
-    source: Option<String>,
-  ) -> Result<String, AnyError> {
+    source: Option<Cow<'a, str>>,
+  ) -> Result<Cow<'a, str>, AnyError> {
     let mut temp_var_count = 0;
 
     let analysis = self
@@ -108,7 +115,7 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     };
 
     let mut source = vec![
-      r#"import {createRequire as __internalCreateRequire} from "node:module";
+      r#"import {createRequire as __internalCreateRequire, Module as __internalModule } from "node:module";
       const require = __internalCreateRequire(import.meta.url);"#
         .to_string(),
     ];
@@ -135,7 +142,12 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     }
 
     source.push(format!(
-      "const mod = require(\"{}\");",
+      r#"let mod;
+      if (import.meta.main) {{
+        mod = __internalModule._load("{0}", null, true)
+      }} else {{
+        mod = require("{0}");
+      }}"#,
       url_to_file_path(entry_specifier)
         .unwrap()
         .to_str()
@@ -159,7 +171,7 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     source.push("export default mod;".to_string());
 
     let translated_source = source.join("\n");
-    Ok(translated_source)
+    Ok(Cow::Owned(translated_source))
   }
 
   async fn analyze_reexports<'a>(
@@ -174,7 +186,7 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     struct Analysis {
       reexport_specifier: url::Url,
       referrer: url::Url,
-      analysis: CjsAnalysis,
+      analysis: CjsAnalysis<'static>,
     }
 
     type AnalysisFuture<'a> = LocalBoxFuture<'a, Result<Analysis, AnyError>>;
@@ -329,8 +341,9 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     }?;
 
     let package_json_path = module_dir.join("package.json");
-    let maybe_package_json =
-      load_pkg_json(self.env.pkg_json_fs(), &package_json_path)?;
+    let maybe_package_json = self
+      .pkg_json_resolver
+      .load_package_json(&package_json_path)?;
     if let Some(package_json) = maybe_package_json {
       if let Some(exports) = &package_json.exports {
         return Some(
@@ -356,8 +369,9 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
         if self.env.is_dir_sync(&d) {
           // subdir might have a package.json that specifies the entrypoint
           let package_json_path = d.join("package.json");
-          let maybe_package_json =
-            load_pkg_json(self.env.pkg_json_fs(), &package_json_path)?;
+          let maybe_package_json = self
+            .pkg_json_resolver
+            .load_package_json(&package_json_path)?;
           if let Some(package_json) = maybe_package_json {
             if let Some(main) = package_json.main(NodeModuleKind::Cjs) {
               return Ok(Some(url_from_file_path(&d.join(main).clean())?));
@@ -382,7 +396,7 @@ impl<TCjsCodeAnalyzer: CjsCodeAnalyzer, TNodeResolverEnv: NodeResolverEnv>
     // as a fallback, attempt to resolve it via the ancestor directories
     let mut last = referrer_path.as_path();
     while let Some(parent) = last.parent() {
-      if !self.npm_resolver.in_npm_package_at_dir_path(parent) {
+      if !self.in_npm_pkg_checker.in_npm_package_at_dir_path(parent) {
         break;
       }
       let path = if parent.ends_with("node_modules") {
diff --git a/resolvers/node/errors.rs b/resolvers/node/errors.rs
index 4ba829eda5..aacbecefb4 100644
--- a/resolvers/node/errors.rs
+++ b/resolvers/node/errors.rs
@@ -81,29 +81,6 @@ pub trait NodeJsErrorCoded {
   fn code(&self) -> NodeJsErrorCode;
 }
 
-kinded_err!(
-  ResolvePkgSubpathFromDenoModuleError,
-  ResolvePkgSubpathFromDenoModuleErrorKind
-);
-
-impl NodeJsErrorCoded for ResolvePkgSubpathFromDenoModuleError {
-  fn code(&self) -> NodeJsErrorCode {
-    use ResolvePkgSubpathFromDenoModuleErrorKind::*;
-    match self.as_kind() {
-      PackageSubpathResolve(e) => e.code(),
-      UrlToNodeResolution(e) => e.code(),
-    }
-  }
-}
-
-#[derive(Debug, Error)]
-pub enum ResolvePkgSubpathFromDenoModuleErrorKind {
-  #[error(transparent)]
-  PackageSubpathResolve(#[from] PackageSubpathResolveError),
-  #[error(transparent)]
-  UrlToNodeResolution(#[from] UrlToNodeResolutionError),
-}
-
 // todo(https://github.com/denoland/deno_core/issues/810): make this a TypeError
 #[derive(Debug, Clone, Error)]
 #[error(
@@ -394,37 +371,6 @@ impl NodeJsErrorCoded for CanonicalizingPkgJsonDirError {
   }
 }
 
-#[derive(Debug, Error)]
-#[error("TypeScript files are not supported in npm packages: {specifier}")]
-pub struct TypeScriptNotSupportedInNpmError {
-  pub specifier: Url,
-}
-
-impl NodeJsErrorCoded for TypeScriptNotSupportedInNpmError {
-  fn code(&self) -> NodeJsErrorCode {
-    NodeJsErrorCode::ERR_UNKNOWN_FILE_EXTENSION
-  }
-}
-
-kinded_err!(UrlToNodeResolutionError, UrlToNodeResolutionErrorKind);
-
-impl NodeJsErrorCoded for UrlToNodeResolutionError {
-  fn code(&self) -> NodeJsErrorCode {
-    match self.as_kind() {
-      UrlToNodeResolutionErrorKind::TypeScriptNotSupported(e) => e.code(),
-      UrlToNodeResolutionErrorKind::ClosestPkgJson(e) => e.code(),
-    }
-  }
-}
-
-#[derive(Debug, Error)]
-pub enum UrlToNodeResolutionErrorKind {
-  #[error(transparent)]
-  TypeScriptNotSupported(#[from] TypeScriptNotSupportedInNpmError),
-  #[error(transparent)]
-  ClosestPkgJson(#[from] ClosestPkgJsonError),
-}
-
 // todo(https://github.com/denoland/deno_core/issues/810): make this a TypeError
 #[derive(Debug, Error)]
 #[error(
@@ -533,8 +479,6 @@ pub enum NodeResolveErrorKind {
   TypesNotFound(#[from] TypesNotFoundError),
   #[error(transparent)]
   FinalizeResolution(#[from] FinalizeResolutionError),
-  #[error(transparent)]
-  UrlToNodeResolution(#[from] UrlToNodeResolutionError),
 }
 
 kinded_err!(FinalizeResolutionError, FinalizeResolutionErrorKind);
@@ -728,8 +672,6 @@ pub enum ResolvePkgJsonBinExportError {
   MissingPkgJson { pkg_json_path: PathBuf },
   #[error("Failed resolving binary export. {message}")]
   InvalidBinProperty { message: String },
-  #[error(transparent)]
-  UrlToNodeResolution(#[from] UrlToNodeResolutionError),
 }
 
 #[derive(Debug, Error)]
diff --git a/resolvers/node/lib.rs b/resolvers/node/lib.rs
index f03f770486..18b0a85363 100644
--- a/resolvers/node/lib.rs
+++ b/resolvers/node/lib.rs
@@ -13,9 +13,12 @@ mod resolution;
 mod sync;
 
 pub use deno_package_json::PackageJson;
+pub use npm::InNpmPackageChecker;
+pub use npm::InNpmPackageCheckerRc;
 pub use npm::NpmResolver;
 pub use npm::NpmResolverRc;
-pub use package_json::load_pkg_json;
+pub use package_json::PackageJsonResolver;
+pub use package_json::PackageJsonResolverRc;
 pub use package_json::PackageJsonThreadLocalCache;
 pub use path::PathClean;
 pub use resolution::parse_npm_pkg_name;
diff --git a/resolvers/node/npm.rs b/resolvers/node/npm.rs
index 6b5f21db62..2132f0b545 100644
--- a/resolvers/node/npm.rs
+++ b/resolvers/node/npm.rs
@@ -22,7 +22,13 @@ pub trait NpmResolver: std::fmt::Debug + MaybeSend + MaybeSync {
     specifier: &str,
     referrer: &Url,
   ) -> Result<PathBuf, errors::PackageFolderResolveError>;
+}
 
+#[allow(clippy::disallowed_types)]
+pub type InNpmPackageCheckerRc = crate::sync::MaybeArc<dyn InNpmPackageChecker>;
+
+/// Checks if a provided specifier is in an npm package.
+pub trait InNpmPackageChecker: std::fmt::Debug + MaybeSend + MaybeSync {
   fn in_npm_package(&self, specifier: &Url) -> bool;
 
   fn in_npm_package_at_dir_path(&self, path: &Path) -> bool {
diff --git a/resolvers/node/package_json.rs b/resolvers/node/package_json.rs
index de750f1d7e..6967779e5d 100644
--- a/resolvers/node/package_json.rs
+++ b/resolvers/node/package_json.rs
@@ -2,15 +2,21 @@
 
 use deno_package_json::PackageJson;
 use deno_package_json::PackageJsonRc;
+use deno_path_util::strip_unc_prefix;
 use std::cell::RefCell;
 use std::collections::HashMap;
 use std::io::ErrorKind;
 use std::path::Path;
 use std::path::PathBuf;
+use url::Url;
 
+use crate::env::NodeResolverEnv;
+use crate::errors::CanonicalizingPkgJsonDirError;
+use crate::errors::ClosestPkgJsonError;
 use crate::errors::PackageJsonLoadError;
 
-// use a thread local cache so that workers have their own distinct cache
+// todo(dsherret): this isn't exactly correct and we should change it to instead
+// be created per worker and passed down as a ctor arg to the pkg json resolver
 thread_local! {
   static CACHE: RefCell<HashMap<PathBuf, PackageJsonRc>> = RefCell::new(HashMap::new());
 }
@@ -33,21 +39,91 @@ impl deno_package_json::PackageJsonCache for PackageJsonThreadLocalCache {
   }
 }
 
-/// Helper to load a package.json file using the thread local cache
-/// in node_resolver.
-pub fn load_pkg_json(
-  fs: &dyn deno_package_json::fs::DenoPkgJsonFs,
-  path: &Path,
-) -> Result<Option<PackageJsonRc>, PackageJsonLoadError> {
-  let result =
-    PackageJson::load_from_path(path, fs, Some(&PackageJsonThreadLocalCache));
-  match result {
-    Ok(pkg_json) => Ok(Some(pkg_json)),
-    Err(deno_package_json::PackageJsonLoadError::Io { source, .. })
-      if source.kind() == ErrorKind::NotFound =>
-    {
+#[allow(clippy::disallowed_types)]
+pub type PackageJsonResolverRc<TEnv> =
+  crate::sync::MaybeArc<PackageJsonResolver<TEnv>>;
+
+#[derive(Debug)]
+pub struct PackageJsonResolver<TEnv: NodeResolverEnv> {
+  env: TEnv,
+}
+
+impl<TEnv: NodeResolverEnv> PackageJsonResolver<TEnv> {
+  pub fn new(env: TEnv) -> Self {
+    Self { env }
+  }
+
+  pub fn get_closest_package_json(
+    &self,
+    url: &Url,
+  ) -> Result<Option<PackageJsonRc>, ClosestPkgJsonError> {
+    let Ok(file_path) = deno_path_util::url_to_file_path(url) else {
+      return Ok(None);
+    };
+    self.get_closest_package_json_from_path(&file_path)
+  }
+
+  pub fn get_closest_package_json_from_path(
+    &self,
+    file_path: &Path,
+  ) -> Result<Option<PackageJsonRc>, ClosestPkgJsonError> {
+    // we use this for deno compile using byonm because the script paths
+    // won't be in virtual file system, but the package.json paths will be
+    fn canonicalize_first_ancestor_exists<TEnv: NodeResolverEnv>(
+      dir_path: &Path,
+      env: &TEnv,
+    ) -> Result<Option<PathBuf>, std::io::Error> {
+      for ancestor in dir_path.ancestors() {
+        match env.realpath_sync(ancestor) {
+          Ok(dir_path) => return Ok(Some(dir_path)),
+          Err(err) if err.kind() == std::io::ErrorKind::NotFound => {
+            // keep searching
+          }
+          Err(err) => return Err(err),
+        }
+      }
       Ok(None)
     }
-    Err(err) => Err(PackageJsonLoadError(err)),
+
+    let parent_dir = file_path.parent().unwrap();
+    let Some(start_dir) = canonicalize_first_ancestor_exists(
+      parent_dir, &self.env,
+    )
+    .map_err(|source| CanonicalizingPkgJsonDirError {
+      dir_path: parent_dir.to_path_buf(),
+      source,
+    })?
+    else {
+      return Ok(None);
+    };
+    let start_dir = strip_unc_prefix(start_dir);
+    for current_dir in start_dir.ancestors() {
+      let package_json_path = current_dir.join("package.json");
+      if let Some(pkg_json) = self.load_package_json(&package_json_path)? {
+        return Ok(Some(pkg_json));
+      }
+    }
+
+    Ok(None)
+  }
+
+  pub fn load_package_json(
+    &self,
+    path: &Path,
+  ) -> Result<Option<PackageJsonRc>, PackageJsonLoadError> {
+    let result = PackageJson::load_from_path(
+      path,
+      self.env.pkg_json_fs(),
+      Some(&PackageJsonThreadLocalCache),
+    );
+    match result {
+      Ok(pkg_json) => Ok(Some(pkg_json)),
+      Err(deno_package_json::PackageJsonLoadError::Io { source, .. })
+        if source.kind() == ErrorKind::NotFound =>
+      {
+        Ok(None)
+      }
+      Err(err) => Err(PackageJsonLoadError(err)),
+    }
   }
 }
diff --git a/resolvers/node/resolution.rs b/resolvers/node/resolution.rs
index 811583a5ee..d44539e978 100644
--- a/resolvers/node/resolution.rs
+++ b/resolvers/node/resolution.rs
@@ -6,9 +6,6 @@ use std::path::PathBuf;
 
 use anyhow::bail;
 use anyhow::Error as AnyError;
-use deno_media_type::MediaType;
-use deno_package_json::PackageJsonRc;
-use deno_path_util::strip_unc_prefix;
 use deno_path_util::url_from_file_path;
 use serde_json::Map;
 use serde_json::Value;
@@ -16,8 +13,6 @@ use url::Url;
 
 use crate::env::NodeResolverEnv;
 use crate::errors;
-use crate::errors::CanonicalizingPkgJsonDirError;
-use crate::errors::ClosestPkgJsonError;
 use crate::errors::DataUrlReferrerError;
 use crate::errors::FinalizeResolutionError;
 use crate::errors::InvalidModuleSpecifierError;
@@ -32,7 +27,6 @@ use crate::errors::PackageExportsResolveError;
 use crate::errors::PackageImportNotDefinedError;
 use crate::errors::PackageImportsResolveError;
 use crate::errors::PackageImportsResolveErrorKind;
-use crate::errors::PackageJsonLoadError;
 use crate::errors::PackagePathNotExportedError;
 use crate::errors::PackageResolveError;
 use crate::errors::PackageSubpathResolveError;
@@ -42,14 +36,13 @@ use crate::errors::PackageTargetResolveError;
 use crate::errors::PackageTargetResolveErrorKind;
 use crate::errors::ResolveBinaryCommandsError;
 use crate::errors::ResolvePkgJsonBinExportError;
-use crate::errors::ResolvePkgSubpathFromDenoModuleError;
-use crate::errors::TypeScriptNotSupportedInNpmError;
 use crate::errors::TypesNotFoundError;
 use crate::errors::TypesNotFoundErrorData;
 use crate::errors::UnsupportedDirImportError;
 use crate::errors::UnsupportedEsmUrlSchemeError;
-use crate::errors::UrlToNodeResolutionError;
+use crate::npm::InNpmPackageCheckerRc;
 use crate::NpmResolverRc;
+use crate::PackageJsonResolverRc;
 use crate::PathClean;
 use deno_package_json::PackageJson;
 
@@ -73,16 +66,14 @@ impl NodeResolutionMode {
 
 #[derive(Debug)]
 pub enum NodeResolution {
-  Esm(Url),
-  CommonJs(Url),
+  Module(Url),
   BuiltIn(String),
 }
 
 impl NodeResolution {
   pub fn into_url(self) -> Url {
     match self {
-      Self::Esm(u) => u,
-      Self::CommonJs(u) => u,
+      Self::Module(u) => u,
       Self::BuiltIn(specifier) => {
         if specifier.starts_with("node:") {
           Url::parse(&specifier).unwrap()
@@ -92,42 +83,6 @@ impl NodeResolution {
       }
     }
   }
-
-  pub fn into_specifier_and_media_type(
-    resolution: Option<Self>,
-  ) -> (Url, MediaType) {
-    match resolution {
-      Some(NodeResolution::CommonJs(specifier)) => {
-        let media_type = MediaType::from_specifier(&specifier);
-        (
-          specifier,
-          match media_type {
-            MediaType::JavaScript | MediaType::Jsx => MediaType::Cjs,
-            MediaType::TypeScript | MediaType::Tsx => MediaType::Cts,
-            MediaType::Dts => MediaType::Dcts,
-            _ => media_type,
-          },
-        )
-      }
-      Some(NodeResolution::Esm(specifier)) => {
-        let media_type = MediaType::from_specifier(&specifier);
-        (
-          specifier,
-          match media_type {
-            MediaType::JavaScript | MediaType::Jsx => MediaType::Mjs,
-            MediaType::TypeScript | MediaType::Tsx => MediaType::Mts,
-            MediaType::Dts => MediaType::Dmts,
-            _ => media_type,
-          },
-        )
-      }
-      Some(resolution) => (resolution.into_url(), MediaType::Dts),
-      None => (
-        Url::parse("internal:///missing_dependency.d.ts").unwrap(),
-        MediaType::Dts,
-      ),
-    }
-  }
 }
 
 #[allow(clippy::disallowed_types)]
@@ -136,16 +91,28 @@ pub type NodeResolverRc<TEnv> = crate::sync::MaybeArc<NodeResolver<TEnv>>;
 #[derive(Debug)]
 pub struct NodeResolver<TEnv: NodeResolverEnv> {
   env: TEnv,
+  in_npm_pkg_checker: InNpmPackageCheckerRc,
   npm_resolver: NpmResolverRc,
+  pkg_json_resolver: PackageJsonResolverRc<TEnv>,
 }
 
 impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
-  pub fn new(env: TEnv, npm_resolver: NpmResolverRc) -> Self {
-    Self { env, npm_resolver }
+  pub fn new(
+    env: TEnv,
+    in_npm_pkg_checker: InNpmPackageCheckerRc,
+    npm_resolver: NpmResolverRc,
+    pkg_json_resolver: PackageJsonResolverRc<TEnv>,
+  ) -> Self {
+    Self {
+      env,
+      in_npm_pkg_checker,
+      npm_resolver,
+      pkg_json_resolver,
+    }
   }
 
   pub fn in_npm_package(&self, specifier: &Url) -> bool {
-    self.npm_resolver.in_npm_package(specifier)
+    self.in_npm_pkg_checker.in_npm_package(specifier)
   }
 
   /// This function is an implementation of `defaultResolve` in
@@ -166,7 +133,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
 
     if let Ok(url) = Url::parse(specifier) {
       if url.scheme() == "data" {
-        return Ok(NodeResolution::Esm(url));
+        return Ok(NodeResolution::Module(url));
       }
 
       if let Some(module_name) =
@@ -191,7 +158,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
         let url = referrer
           .join(specifier)
           .map_err(|source| DataUrlReferrerError { source })?;
-        return Ok(NodeResolution::Esm(url));
+        return Ok(NodeResolution::Module(url));
       }
     }
 
@@ -212,7 +179,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     };
 
     let url = self.finalize_resolution(url, Some(referrer))?;
-    let resolve_response = self.url_to_node_resolution(url)?;
+    let resolve_response = NodeResolution::Module(url);
     // TODO(bartlomieju): skipped checking errors for commonJS resolution and
     // "preserveSymlinksMain"/"preserveSymlinks" options.
     Ok(resolve_response)
@@ -236,6 +203,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       })?)
     } else if specifier.starts_with('#') {
       let pkg_config = self
+        .pkg_json_resolver
         .get_closest_package_json(referrer)
         .map_err(PackageImportsResolveErrorKind::ClosestPkgJson)
         .map_err(|err| PackageImportsResolveError(Box::new(err)))?;
@@ -332,7 +300,7 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     package_subpath: Option<&str>,
     maybe_referrer: Option<&Url>,
     mode: NodeResolutionMode,
-  ) -> Result<NodeResolution, ResolvePkgSubpathFromDenoModuleError> {
+  ) -> Result<Url, PackageSubpathResolveError> {
     let node_module_kind = NodeModuleKind::Esm;
     let package_subpath = package_subpath
       .map(|s| format!("./{s}"))
@@ -345,10 +313,9 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       DEFAULT_CONDITIONS,
       mode,
     )?;
-    let resolve_response = self.url_to_node_resolution(resolved_url)?;
     // TODO(bartlomieju): skipped checking errors for commonJS resolution and
     // "preserveSymlinksMain"/"preserveSymlinks" options.
-    Ok(resolve_response)
+    Ok(resolved_url)
   }
 
   pub fn resolve_binary_commands(
@@ -356,7 +323,9 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     package_folder: &Path,
   ) -> Result<Vec<String>, ResolveBinaryCommandsError> {
     let pkg_json_path = package_folder.join("package.json");
-    let Some(package_json) = self.load_package_json(&pkg_json_path)? else {
+    let Some(package_json) =
+      self.pkg_json_resolver.load_package_json(&pkg_json_path)?
+    else {
       return Ok(Vec::new());
     };
 
@@ -381,9 +350,11 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     &self,
     package_folder: &Path,
     sub_path: Option<&str>,
-  ) -> Result<NodeResolution, ResolvePkgJsonBinExportError> {
+  ) -> Result<Url, ResolvePkgJsonBinExportError> {
     let pkg_json_path = package_folder.join("package.json");
-    let Some(package_json) = self.load_package_json(&pkg_json_path)? else {
+    let Some(package_json) =
+      self.pkg_json_resolver.load_package_json(&pkg_json_path)?
+    else {
       return Err(ResolvePkgJsonBinExportError::MissingPkgJson {
         pkg_json_path,
       });
@@ -396,37 +367,9 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
       })?;
     let url = url_from_file_path(&package_folder.join(bin_entry)).unwrap();
 
-    let resolve_response = self.url_to_node_resolution(url)?;
     // TODO(bartlomieju): skipped checking errors for commonJS resolution and
     // "preserveSymlinksMain"/"preserveSymlinks" options.
-    Ok(resolve_response)
-  }
-
-  pub fn url_to_node_resolution(
-    &self,
-    url: Url,
-  ) -> Result<NodeResolution, UrlToNodeResolutionError> {
-    let url_str = url.as_str().to_lowercase();
-    if url_str.starts_with("http") || url_str.ends_with(".json") {
-      Ok(NodeResolution::Esm(url))
-    } else if url_str.ends_with(".js") || url_str.ends_with(".d.ts") {
-      let maybe_package_config = self.get_closest_package_json(&url)?;
-      match maybe_package_config {
-        Some(c) if c.typ == "module" => Ok(NodeResolution::Esm(url)),
-        Some(_) => Ok(NodeResolution::CommonJs(url)),
-        None => Ok(NodeResolution::Esm(url)),
-      }
-    } else if url_str.ends_with(".mjs") || url_str.ends_with(".d.mts") {
-      Ok(NodeResolution::Esm(url))
-    } else if url_str.ends_with(".ts") || url_str.ends_with(".mts") {
-      if self.in_npm_package(&url) {
-        Err(TypeScriptNotSupportedInNpmError { specifier: url }.into())
-      } else {
-        Ok(NodeResolution::Esm(url))
-      }
-    } else {
-      Ok(NodeResolution::CommonJs(url))
-    }
+    Ok(url)
   }
 
   /// Checks if the resolved file has a corresponding declaration file.
@@ -1101,7 +1044,9 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     let (package_name, package_subpath, _is_scoped) =
       parse_npm_pkg_name(specifier, referrer)?;
 
-    if let Some(package_config) = self.get_closest_package_json(referrer)? {
+    if let Some(package_config) =
+      self.pkg_json_resolver.get_closest_package_json(referrer)?
+    {
       // ResolveSelf
       if package_config.name.as_ref() == Some(&package_name) {
         if let Some(exports) = &package_config.exports {
@@ -1216,7 +1161,10 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     mode: NodeResolutionMode,
   ) -> Result<Url, PackageSubpathResolveError> {
     let package_json_path = package_dir_path.join("package.json");
-    match self.load_package_json(&package_json_path)? {
+    match self
+      .pkg_json_resolver
+      .load_package_json(&package_json_path)?
+    {
       Some(pkg_json) => self.resolve_package_subpath(
         &pkg_json,
         package_subpath,
@@ -1337,70 +1285,6 @@ impl<TEnv: NodeResolverEnv> NodeResolver<TEnv> {
     }
   }
 
-  pub fn get_closest_package_json(
-    &self,
-    url: &Url,
-  ) -> Result<Option<PackageJsonRc>, ClosestPkgJsonError> {
-    let Ok(file_path) = deno_path_util::url_to_file_path(url) else {
-      return Ok(None);
-    };
-    self.get_closest_package_json_from_path(&file_path)
-  }
-
-  pub fn get_closest_package_json_from_path(
-    &self,
-    file_path: &Path,
-  ) -> Result<Option<PackageJsonRc>, ClosestPkgJsonError> {
-    // we use this for deno compile using byonm because the script paths
-    // won't be in virtual file system, but the package.json paths will be
-    fn canonicalize_first_ancestor_exists(
-      dir_path: &Path,
-      env: &dyn NodeResolverEnv,
-    ) -> Result<Option<PathBuf>, std::io::Error> {
-      for ancestor in dir_path.ancestors() {
-        match env.realpath_sync(ancestor) {
-          Ok(dir_path) => return Ok(Some(dir_path)),
-          Err(err) if err.kind() == std::io::ErrorKind::NotFound => {
-            // keep searching
-          }
-          Err(err) => return Err(err),
-        }
-      }
-      Ok(None)
-    }
-
-    let parent_dir = file_path.parent().unwrap();
-    let Some(start_dir) = canonicalize_first_ancestor_exists(
-      parent_dir, &self.env,
-    )
-    .map_err(|source| CanonicalizingPkgJsonDirError {
-      dir_path: parent_dir.to_path_buf(),
-      source,
-    })?
-    else {
-      return Ok(None);
-    };
-    let start_dir = strip_unc_prefix(start_dir);
-    for current_dir in start_dir.ancestors() {
-      let package_json_path = current_dir.join("package.json");
-      if let Some(pkg_json) = self.load_package_json(&package_json_path)? {
-        return Ok(Some(pkg_json));
-      }
-    }
-
-    Ok(None)
-  }
-
-  pub fn load_package_json(
-    &self,
-    package_json_path: &Path,
-  ) -> Result<Option<PackageJsonRc>, PackageJsonLoadError> {
-    crate::package_json::load_pkg_json(
-      self.env.pkg_json_fs(),
-      package_json_path,
-    )
-  }
-
   pub(super) fn legacy_main_resolve(
     &self,
     package_json: &PackageJson,
diff --git a/runtime/Cargo.toml b/runtime/Cargo.toml
index ba9dc6243f..c4c0c8ff9b 100644
--- a/runtime/Cargo.toml
+++ b/runtime/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_runtime"
-version = "0.180.0"
+version = "0.184.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
@@ -100,6 +100,7 @@ deno_websocket.workspace = true
 deno_webstorage.workspace = true
 node_resolver = { workspace = true, features = ["sync"] }
 
+color-print.workspace = true
 dlopen2.workspace = true
 encoding_rs.workspace = true
 fastwebsockets.workspace = true
@@ -116,10 +117,12 @@ once_cell.workspace = true
 percent-encoding.workspace = true
 regex.workspace = true
 rustyline = { workspace = true, features = ["custom-bindings"] }
+same-file = "1.0.6"
 serde.workspace = true
 signal-hook = "0.3.17"
 signal-hook-registry = "1.4.0"
 tempfile.workspace = true
+thiserror.workspace = true
 tokio.workspace = true
 tokio-metrics.workspace = true
 twox-hash.workspace = true
diff --git a/runtime/errors.rs b/runtime/errors.rs
index 694402773e..ada26ec35f 100644
--- a/runtime/errors.rs
+++ b/runtime/errors.rs
@@ -9,10 +9,55 @@
 //!   Diagnostics are compile-time type errors, whereas JsErrors are runtime
 //!   exceptions.
 
+use crate::ops::fs_events::FsEventsError;
+use crate::ops::http::HttpStartError;
+use crate::ops::os::OsError;
+use crate::ops::process::ProcessError;
+use crate::ops::signal::SignalError;
+use crate::ops::tty::TtyError;
+use crate::ops::web_worker::SyncFetchError;
+use crate::ops::worker_host::CreateWorkerError;
+use deno_broadcast_channel::BroadcastChannelError;
+use deno_cache::CacheError;
+use deno_canvas::CanvasError;
 use deno_core::error::AnyError;
 use deno_core::serde_json;
 use deno_core::url;
 use deno_core::ModuleResolutionError;
+use deno_cron::CronError;
+use deno_crypto::DecryptError;
+use deno_crypto::EncryptError;
+use deno_crypto::ExportKeyError;
+use deno_crypto::GenerateKeyError;
+use deno_crypto::ImportKeyError;
+use deno_fetch::FetchError;
+use deno_fetch::HttpClientCreateError;
+use deno_ffi::CallError;
+use deno_ffi::CallbackError;
+use deno_ffi::DlfcnError;
+use deno_ffi::IRError;
+use deno_ffi::ReprError;
+use deno_ffi::StaticError;
+use deno_fs::FsOpsError;
+use deno_http::HttpError;
+use deno_http::HttpNextError;
+use deno_http::WebSocketUpgradeError;
+use deno_io::fs::FsError;
+use deno_kv::KvCheckError;
+use deno_kv::KvError;
+use deno_kv::KvMutationError;
+use deno_napi::NApiError;
+use deno_net::ops::NetError;
+use deno_tls::TlsError;
+use deno_web::BlobError;
+use deno_web::CompressionError;
+use deno_web::MessagePortError;
+use deno_web::StreamResourceError;
+use deno_web::WebError;
+use deno_websocket::HandshakeError;
+use deno_websocket::WebsocketError;
+use deno_webstorage::WebStorageError;
+use rustyline::error::ReadlineError;
 use std::env;
 use std::error::Error;
 use std::io;
@@ -153,12 +198,1137 @@ pub fn get_nix_error_class(error: &nix::Error) -> &'static str {
   }
 }
 
+fn get_webgpu_error_class(e: &deno_webgpu::InitError) -> &'static str {
+  match e {
+    deno_webgpu::InitError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::InitError::InvalidAdapter(_) => "Error",
+    deno_webgpu::InitError::RequestDevice(_) => "DOMExceptionOperationError",
+    deno_webgpu::InitError::InvalidDevice(_) => "Error",
+  }
+}
+
+fn get_webgpu_buffer_error_class(
+  e: &deno_webgpu::buffer::BufferError,
+) -> &'static str {
+  match e {
+    deno_webgpu::buffer::BufferError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::buffer::BufferError::InvalidUsage => "TypeError",
+    deno_webgpu::buffer::BufferError::Access(_) => "DOMExceptionOperationError",
+  }
+}
+
+fn get_webgpu_bundle_error_class(
+  e: &deno_webgpu::bundle::BundleError,
+) -> &'static str {
+  match e {
+    deno_webgpu::bundle::BundleError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::bundle::BundleError::InvalidSize => "TypeError",
+  }
+}
+
+fn get_webgpu_byow_error_class(
+  e: &deno_webgpu::byow::ByowError,
+) -> &'static str {
+  match e {
+    deno_webgpu::byow::ByowError::WebGPUNotInitiated => "TypeError",
+    deno_webgpu::byow::ByowError::InvalidParameters => "TypeError",
+    deno_webgpu::byow::ByowError::CreateSurface(_) => "Error",
+    deno_webgpu::byow::ByowError::InvalidSystem => "TypeError",
+    #[cfg(any(
+      target_os = "windows",
+      target_os = "linux",
+      target_os = "freebsd",
+      target_os = "openbsd"
+    ))]
+    deno_webgpu::byow::ByowError::NullWindow => "TypeError",
+    #[cfg(any(
+      target_os = "linux",
+      target_os = "freebsd",
+      target_os = "openbsd"
+    ))]
+    deno_webgpu::byow::ByowError::NullDisplay => "TypeError",
+    #[cfg(target_os = "macos")]
+    deno_webgpu::byow::ByowError::NSViewDisplay => "TypeError",
+  }
+}
+
+fn get_webgpu_render_pass_error_class(
+  e: &deno_webgpu::render_pass::RenderPassError,
+) -> &'static str {
+  match e {
+    deno_webgpu::render_pass::RenderPassError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::render_pass::RenderPassError::InvalidSize => "TypeError",
+  }
+}
+
+fn get_webgpu_surface_error_class(
+  e: &deno_webgpu::surface::SurfaceError,
+) -> &'static str {
+  match e {
+    deno_webgpu::surface::SurfaceError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    deno_webgpu::surface::SurfaceError::Surface(_) => "Error",
+    deno_webgpu::surface::SurfaceError::InvalidStatus => "Error",
+  }
+}
+
+fn get_crypto_decrypt_error_class(e: &DecryptError) -> &'static str {
+  match e {
+    DecryptError::General(e) => get_crypto_shared_error_class(e),
+    DecryptError::Pkcs1(_) => "Error",
+    DecryptError::Failed => "DOMExceptionOperationError",
+    DecryptError::InvalidLength => "TypeError",
+    DecryptError::InvalidCounterLength => "TypeError",
+    DecryptError::InvalidTagLength => "TypeError",
+    DecryptError::InvalidKeyOrIv => "DOMExceptionOperationError",
+    DecryptError::TooMuchData => "DOMExceptionOperationError",
+    DecryptError::InvalidIvLength => "TypeError",
+    DecryptError::Rsa(_) => "DOMExceptionOperationError",
+  }
+}
+
+fn get_crypto_encrypt_error_class(e: &EncryptError) -> &'static str {
+  match e {
+    EncryptError::General(e) => get_crypto_shared_error_class(e),
+    EncryptError::InvalidKeyOrIv => "DOMExceptionOperationError",
+    EncryptError::Failed => "DOMExceptionOperationError",
+    EncryptError::InvalidLength => "TypeError",
+    EncryptError::InvalidIvLength => "TypeError",
+    EncryptError::InvalidCounterLength => "TypeError",
+    EncryptError::TooMuchData => "DOMExceptionOperationError",
+  }
+}
+
+fn get_crypto_shared_error_class(e: &deno_crypto::SharedError) -> &'static str {
+  match e {
+    deno_crypto::SharedError::ExpectedValidPrivateKey => "TypeError",
+    deno_crypto::SharedError::ExpectedValidPublicKey => "TypeError",
+    deno_crypto::SharedError::ExpectedValidPrivateECKey => "TypeError",
+    deno_crypto::SharedError::ExpectedValidPublicECKey => "TypeError",
+    deno_crypto::SharedError::ExpectedPrivateKey => "TypeError",
+    deno_crypto::SharedError::ExpectedPublicKey => "TypeError",
+    deno_crypto::SharedError::ExpectedSecretKey => "TypeError",
+    deno_crypto::SharedError::FailedDecodePrivateKey => {
+      "DOMExceptionOperationError"
+    }
+    deno_crypto::SharedError::FailedDecodePublicKey => {
+      "DOMExceptionOperationError"
+    }
+    deno_crypto::SharedError::UnsupportedFormat => {
+      "DOMExceptionNotSupportedError"
+    }
+  }
+}
+
+fn get_crypto_ed25519_error_class(
+  e: &deno_crypto::Ed25519Error,
+) -> &'static str {
+  match e {
+    deno_crypto::Ed25519Error::FailedExport => "DOMExceptionOperationError",
+    deno_crypto::Ed25519Error::Der(_) => "Error",
+    deno_crypto::Ed25519Error::KeyRejected(_) => "Error",
+  }
+}
+
+fn get_crypto_export_key_error_class(e: &ExportKeyError) -> &'static str {
+  match e {
+    ExportKeyError::General(e) => get_crypto_shared_error_class(e),
+    ExportKeyError::Der(_) => "Error",
+    ExportKeyError::UnsupportedNamedCurve => "DOMExceptionNotSupportedError",
+  }
+}
+
+fn get_crypto_generate_key_error_class(e: &GenerateKeyError) -> &'static str {
+  match e {
+    GenerateKeyError::General(e) => get_crypto_shared_error_class(e),
+    GenerateKeyError::BadPublicExponent => "DOMExceptionOperationError",
+    GenerateKeyError::InvalidHMACKeyLength => "DOMExceptionOperationError",
+    GenerateKeyError::FailedRSAKeySerialization => "DOMExceptionOperationError",
+    GenerateKeyError::InvalidAESKeyLength => "DOMExceptionOperationError",
+    GenerateKeyError::FailedRSAKeyGeneration => "DOMExceptionOperationError",
+    GenerateKeyError::FailedECKeyGeneration => "DOMExceptionOperationError",
+    GenerateKeyError::FailedKeyGeneration => "DOMExceptionOperationError",
+  }
+}
+
+fn get_crypto_import_key_error_class(e: &ImportKeyError) -> &'static str {
+  match e {
+    ImportKeyError::General(e) => get_crypto_shared_error_class(e),
+    ImportKeyError::InvalidModulus => "DOMExceptionDataError",
+    ImportKeyError::InvalidPublicExponent => "DOMExceptionDataError",
+    ImportKeyError::InvalidPrivateExponent => "DOMExceptionDataError",
+    ImportKeyError::InvalidFirstPrimeFactor => "DOMExceptionDataError",
+    ImportKeyError::InvalidSecondPrimeFactor => "DOMExceptionDataError",
+    ImportKeyError::InvalidFirstCRTExponent => "DOMExceptionDataError",
+    ImportKeyError::InvalidSecondCRTExponent => "DOMExceptionDataError",
+    ImportKeyError::InvalidCRTCoefficient => "DOMExceptionDataError",
+    ImportKeyError::InvalidB64Coordinate => "DOMExceptionDataError",
+    ImportKeyError::InvalidRSAPublicKey => "DOMExceptionDataError",
+    ImportKeyError::InvalidRSAPrivateKey => "DOMExceptionDataError",
+    ImportKeyError::UnsupportedAlgorithm => "DOMExceptionDataError",
+    ImportKeyError::PublicKeyTooLong => "DOMExceptionDataError",
+    ImportKeyError::PrivateKeyTooLong => "DOMExceptionDataError",
+    ImportKeyError::InvalidP256ECPoint => "DOMExceptionDataError",
+    ImportKeyError::InvalidP384ECPoint => "DOMExceptionDataError",
+    ImportKeyError::InvalidP521ECPoint => "DOMExceptionDataError",
+    ImportKeyError::UnsupportedNamedCurve => "DOMExceptionDataError",
+    ImportKeyError::CurveMismatch => "DOMExceptionDataError",
+    ImportKeyError::InvalidKeyData => "DOMExceptionDataError",
+    ImportKeyError::InvalidJWKPrivateKey => "DOMExceptionDataError",
+    ImportKeyError::EllipticCurve(_) => "DOMExceptionDataError",
+    ImportKeyError::ExpectedValidPkcs8Data => "DOMExceptionDataError",
+    ImportKeyError::MalformedParameters => "DOMExceptionDataError",
+    ImportKeyError::Spki(_) => "DOMExceptionDataError",
+    ImportKeyError::InvalidP256ECSPKIData => "DOMExceptionDataError",
+    ImportKeyError::InvalidP384ECSPKIData => "DOMExceptionDataError",
+    ImportKeyError::InvalidP521ECSPKIData => "DOMExceptionDataError",
+    ImportKeyError::Der(_) => "DOMExceptionDataError",
+  }
+}
+
+fn get_crypto_x448_error_class(e: &deno_crypto::X448Error) -> &'static str {
+  match e {
+    deno_crypto::X448Error::FailedExport => "DOMExceptionOperationError",
+    deno_crypto::X448Error::Der(_) => "Error",
+  }
+}
+
+fn get_crypto_x25519_error_class(e: &deno_crypto::X25519Error) -> &'static str {
+  match e {
+    deno_crypto::X25519Error::FailedExport => "DOMExceptionOperationError",
+    deno_crypto::X25519Error::Der(_) => "Error",
+  }
+}
+
+fn get_crypto_error_class(e: &deno_crypto::Error) -> &'static str {
+  match e {
+    deno_crypto::Error::Der(_) => "Error",
+    deno_crypto::Error::JoinError(_) => "Error",
+    deno_crypto::Error::MissingArgumentHash => "TypeError",
+    deno_crypto::Error::MissingArgumentSaltLength => "TypeError",
+    deno_crypto::Error::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    deno_crypto::Error::UnsupportedAlgorithm => "TypeError",
+    deno_crypto::Error::KeyRejected(_) => "Error",
+    deno_crypto::Error::RSA(_) => "Error",
+    deno_crypto::Error::Pkcs1(_) => "Error",
+    deno_crypto::Error::Unspecified(_) => "Error",
+    deno_crypto::Error::InvalidKeyFormat => "TypeError",
+    deno_crypto::Error::MissingArgumentPublicKey => "TypeError",
+    deno_crypto::Error::P256Ecdsa(_) => "Error",
+    deno_crypto::Error::DecodePrivateKey => "TypeError",
+    deno_crypto::Error::MissingArgumentNamedCurve => "TypeError",
+    deno_crypto::Error::MissingArgumentInfo => "TypeError",
+    deno_crypto::Error::HKDFLengthTooLarge => "DOMExceptionOperationError",
+    deno_crypto::Error::General(e) => get_crypto_shared_error_class(e),
+    deno_crypto::Error::Base64Decode(_) => "Error",
+    deno_crypto::Error::DataInvalidSize => "TypeError",
+    deno_crypto::Error::InvalidKeyLength => "TypeError",
+    deno_crypto::Error::EncryptionError => "DOMExceptionOperationError",
+    deno_crypto::Error::DecryptionError => "DOMExceptionOperationError",
+    deno_crypto::Error::ArrayBufferViewLengthExceeded(_) => {
+      "DOMExceptionQuotaExceededError"
+    }
+  }
+}
+
+fn get_napi_error_class(e: &NApiError) -> &'static str {
+  match e {
+    NApiError::InvalidPath
+    | NApiError::LibLoading(_)
+    | NApiError::ModuleNotFound(_) => "TypeError",
+    NApiError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_web_error_class(e: &WebError) -> &'static str {
+  match e {
+    WebError::Base64Decode => "DOMExceptionInvalidCharacterError",
+    WebError::InvalidEncodingLabel(_) => "RangeError",
+    WebError::BufferTooLong => "TypeError",
+    WebError::ValueTooLarge => "RangeError",
+    WebError::BufferTooSmall => "RangeError",
+    WebError::DataInvalid => "TypeError",
+    WebError::DataError(_) => "Error",
+  }
+}
+
+fn get_web_compression_error_class(e: &CompressionError) -> &'static str {
+  match e {
+    CompressionError::UnsupportedFormat => "TypeError",
+    CompressionError::ResourceClosed => "TypeError",
+    CompressionError::IoTypeError(_) => "TypeError",
+    CompressionError::Io(e) => get_io_error_class(e),
+  }
+}
+
+fn get_web_message_port_error_class(e: &MessagePortError) -> &'static str {
+  match e {
+    MessagePortError::InvalidTransfer => "TypeError",
+    MessagePortError::NotReady => "TypeError",
+    MessagePortError::TransferSelf => "TypeError",
+    MessagePortError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    MessagePortError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_web_stream_resource_error_class(
+  e: &StreamResourceError,
+) -> &'static str {
+  match e {
+    StreamResourceError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    StreamResourceError::Js(_) => "TypeError",
+  }
+}
+
+fn get_web_blob_error_class(e: &BlobError) -> &'static str {
+  match e {
+    BlobError::BlobPartNotFound => "TypeError",
+    BlobError::SizeLargerThanBlobPart => "TypeError",
+    BlobError::BlobURLsNotSupported => "TypeError",
+    BlobError::Url(_) => "Error",
+  }
+}
+
+fn get_ffi_repr_error_class(e: &ReprError) -> &'static str {
+  match e {
+    ReprError::InvalidOffset => "TypeError",
+    ReprError::InvalidArrayBuffer => "TypeError",
+    ReprError::DestinationLengthTooShort => "RangeError",
+    ReprError::InvalidCString => "TypeError",
+    ReprError::CStringTooLong => "TypeError",
+    ReprError::InvalidBool => "TypeError",
+    ReprError::InvalidU8 => "TypeError",
+    ReprError::InvalidI8 => "TypeError",
+    ReprError::InvalidU16 => "TypeError",
+    ReprError::InvalidI16 => "TypeError",
+    ReprError::InvalidU32 => "TypeError",
+    ReprError::InvalidI32 => "TypeError",
+    ReprError::InvalidU64 => "TypeError",
+    ReprError::InvalidI64 => "TypeError",
+    ReprError::InvalidF32 => "TypeError",
+    ReprError::InvalidF64 => "TypeError",
+    ReprError::InvalidPointer => "TypeError",
+    ReprError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_ffi_dlfcn_error_class(e: &DlfcnError) -> &'static str {
+  match e {
+    DlfcnError::RegisterSymbol { .. } => "Error",
+    DlfcnError::Dlopen(_) => "Error",
+    DlfcnError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+    DlfcnError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_ffi_static_error_class(e: &StaticError) -> &'static str {
+  match e {
+    StaticError::Dlfcn(e) => get_ffi_dlfcn_error_class(e),
+    StaticError::InvalidTypeVoid => "TypeError",
+    StaticError::InvalidTypeStruct => "TypeError",
+    StaticError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_ffi_callback_error_class(e: &CallbackError) -> &'static str {
+  match e {
+    CallbackError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+    CallbackError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    CallbackError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_ffi_call_error_class(e: &CallError) -> &'static str {
+  match e {
+    CallError::IR(_) => "TypeError",
+    CallError::NonblockingCallFailure(_) => "Error",
+    CallError::InvalidSymbol(_) => "TypeError",
+    CallError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+    CallError::Callback(e) => get_ffi_callback_error_class(e),
+  }
+}
+
+fn get_webstorage_class_name(e: &WebStorageError) -> &'static str {
+  match e {
+    WebStorageError::ContextNotSupported => "DOMExceptionNotSupportedError",
+    WebStorageError::Sqlite(_) => todo!(),
+    WebStorageError::Io(e) => get_io_error_class(e),
+    WebStorageError::StorageExceeded => "DOMExceptionQuotaExceededError",
+  }
+}
+
+fn get_tls_error_class(e: &TlsError) -> &'static str {
+  match e {
+    TlsError::Rustls(_) => "Error",
+    TlsError::UnableAddPemFileToCert(e) => get_io_error_class(e),
+    TlsError::CertInvalid
+    | TlsError::CertsNotFound
+    | TlsError::KeysNotFound
+    | TlsError::KeyDecode => "InvalidData",
+  }
+}
+
+pub fn get_cron_error_class(e: &CronError) -> &'static str {
+  match e {
+    CronError::Resource(e) => {
+      deno_core::error::get_custom_error_class(e).unwrap_or("Error")
+    }
+    CronError::NameExceeded(_) => "TypeError",
+    CronError::NameInvalid => "TypeError",
+    CronError::AlreadyExists => "TypeError",
+    CronError::TooManyCrons => "TypeError",
+    CronError::InvalidCron => "TypeError",
+    CronError::InvalidBackoff => "TypeError",
+    CronError::AcquireError(_) => "Error",
+    CronError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_canvas_error(e: &CanvasError) -> &'static str {
+  match e {
+    CanvasError::UnsupportedColorType(_) => "TypeError",
+    CanvasError::Image(_) => "Error",
+  }
+}
+
+pub fn get_cache_error(error: &CacheError) -> &'static str {
+  match error {
+    CacheError::Sqlite(_) => "Error",
+    CacheError::JoinError(_) => "Error",
+    CacheError::Resource(err) => {
+      deno_core::error::get_custom_error_class(err).unwrap_or("Error")
+    }
+    CacheError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    CacheError::Io(err) => get_io_error_class(err),
+  }
+}
+
+fn get_broadcast_channel_error(error: &BroadcastChannelError) -> &'static str {
+  match error {
+    BroadcastChannelError::Resource(err) => {
+      deno_core::error::get_custom_error_class(err).unwrap()
+    }
+    BroadcastChannelError::MPSCSendError(_) => "Error",
+    BroadcastChannelError::BroadcastSendError(_) => "Error",
+    BroadcastChannelError::Other(err) => {
+      get_error_class_name(err).unwrap_or("Error")
+    }
+  }
+}
+
+fn get_fetch_error(error: &FetchError) -> &'static str {
+  match error {
+    FetchError::Resource(e) | FetchError::Permission(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    FetchError::NetworkError => "TypeError",
+    FetchError::FsNotGet(_) => "TypeError",
+    FetchError::InvalidUrl(_) => "TypeError",
+    FetchError::InvalidHeaderName(_) => "TypeError",
+    FetchError::InvalidHeaderValue(_) => "TypeError",
+    FetchError::DataUrl(_) => "TypeError",
+    FetchError::Base64(_) => "TypeError",
+    FetchError::BlobNotFound => "TypeError",
+    FetchError::SchemeNotSupported(_) => "TypeError",
+    FetchError::RequestCanceled => "TypeError",
+    FetchError::Http(_) => "Error",
+    FetchError::ClientCreate(e) => get_http_client_create_error(e),
+    FetchError::Url(e) => get_url_parse_error_class(e),
+    FetchError::Method(_) => "TypeError",
+    FetchError::ClientSend(_) => "TypeError",
+    FetchError::RequestBuilderHook(_) => "TypeError",
+    FetchError::Io(e) => get_io_error_class(e),
+    FetchError::Hyper(e) => get_hyper_error_class(e),
+  }
+}
+
+fn get_http_client_create_error(error: &HttpClientCreateError) -> &'static str {
+  match error {
+    HttpClientCreateError::Tls(_) => "TypeError",
+    HttpClientCreateError::InvalidUserAgent(_) => "TypeError",
+    HttpClientCreateError::InvalidProxyUrl => "TypeError",
+    HttpClientCreateError::HttpVersionSelectionInvalid => "TypeError",
+    HttpClientCreateError::RootCertStore(_) => "TypeError",
+  }
+}
+
+fn get_websocket_error(error: &WebsocketError) -> &'static str {
+  match error {
+    WebsocketError::Permission(e) | WebsocketError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    WebsocketError::Url(e) => get_url_parse_error_class(e),
+    WebsocketError::Io(e) => get_io_error_class(e),
+    WebsocketError::WebSocket(_) => "TypeError",
+    WebsocketError::ConnectionFailed(_) => "DOMExceptionNetworkError",
+    WebsocketError::Uri(_) => "Error",
+    WebsocketError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+  }
+}
+
+fn get_websocket_handshake_error(error: &HandshakeError) -> &'static str {
+  match error {
+    HandshakeError::RootStoreError(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    HandshakeError::Tls(e) => get_tls_error_class(e),
+    HandshakeError::MissingPath => "TypeError",
+    HandshakeError::Http(_) => "Error",
+    HandshakeError::InvalidHostname(_) => "TypeError",
+    HandshakeError::Io(e) => get_io_error_class(e),
+    HandshakeError::Rustls(_) => "Error",
+    HandshakeError::H2(_) => "Error",
+    HandshakeError::NoH2Alpn => "Error",
+    HandshakeError::InvalidStatusCode(_) => "Error",
+    HandshakeError::WebSocket(_) => "TypeError",
+    HandshakeError::HeaderName(_) => "TypeError",
+    HandshakeError::HeaderValue(_) => "TypeError",
+  }
+}
+
+fn get_fs_ops_error(error: &FsOpsError) -> &'static str {
+  match error {
+    FsOpsError::Io(e) => get_io_error_class(e),
+    FsOpsError::OperationError(e) => get_fs_error(&e.err),
+    FsOpsError::Permission(e)
+    | FsOpsError::Resource(e)
+    | FsOpsError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    FsOpsError::InvalidUtf8(_) => "InvalidData",
+    FsOpsError::StripPrefix(_) => "Error",
+    FsOpsError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    FsOpsError::InvalidSeekMode(_) => "TypeError",
+    FsOpsError::InvalidControlCharacter(_) => "Error",
+    FsOpsError::InvalidCharacter(_) => "Error",
+    #[cfg(windows)]
+    FsOpsError::InvalidTrailingCharacter => "Error",
+    FsOpsError::NotCapableAccess { .. } => "NotCapable",
+    FsOpsError::NotCapable(_) => "NotCapable",
+  }
+}
+
+fn get_kv_error(error: &KvError) -> &'static str {
+  match error {
+    KvError::DatabaseHandler(e) | KvError::Resource(e) | KvError::Kv(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    KvError::TooManyRanges(_) => "TypeError",
+    KvError::TooManyEntries(_) => "TypeError",
+    KvError::TooManyChecks(_) => "TypeError",
+    KvError::TooManyMutations(_) => "TypeError",
+    KvError::TooManyKeys(_) => "TypeError",
+    KvError::InvalidLimit => "TypeError",
+    KvError::InvalidBoundaryKey => "TypeError",
+    KvError::KeyTooLargeToRead(_) => "TypeError",
+    KvError::KeyTooLargeToWrite(_) => "TypeError",
+    KvError::TotalMutationTooLarge(_) => "TypeError",
+    KvError::TotalKeyTooLarge(_) => "TypeError",
+    KvError::Io(e) => get_io_error_class(e),
+    KvError::QueueMessageNotFound => "TypeError",
+    KvError::StartKeyNotInKeyspace => "TypeError",
+    KvError::EndKeyNotInKeyspace => "TypeError",
+    KvError::StartKeyGreaterThanEndKey => "TypeError",
+    KvError::InvalidCheck(e) => match e {
+      KvCheckError::InvalidVersionstamp => "TypeError",
+      KvCheckError::Io(e) => get_io_error_class(e),
+    },
+    KvError::InvalidMutation(e) => match e {
+      KvMutationError::BigInt(_) => "Error",
+      KvMutationError::Io(e) => get_io_error_class(e),
+      KvMutationError::InvalidMutationWithValue(_) => "TypeError",
+      KvMutationError::InvalidMutationWithoutValue(_) => "TypeError",
+    },
+    KvError::InvalidEnqueue(e) => get_io_error_class(e),
+    KvError::EmptyKey => "TypeError",
+    KvError::ValueTooLarge(_) => "TypeError",
+    KvError::EnqueuePayloadTooLarge(_) => "TypeError",
+    KvError::InvalidCursor => "TypeError",
+    KvError::CursorOutOfBounds => "TypeError",
+    KvError::InvalidRange => "TypeError",
+  }
+}
+
+fn get_net_error(error: &NetError) -> &'static str {
+  match error {
+    NetError::ListenerClosed => "BadResource",
+    NetError::ListenerBusy => "Busy",
+    NetError::SocketClosed => "BadResource",
+    NetError::SocketClosedNotConnected => "NotConnected",
+    NetError::SocketBusy => "Busy",
+    NetError::Io(e) => get_io_error_class(e),
+    NetError::AcceptTaskOngoing => "Busy",
+    NetError::RootCertStore(e)
+    | NetError::Permission(e)
+    | NetError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+    NetError::NoResolvedAddress => "Error",
+    NetError::AddrParse(_) => "Error",
+    NetError::Map(e) => get_net_map_error(e),
+    NetError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    NetError::DnsNotFound(_) => "NotFound",
+    NetError::DnsNotConnected(_) => "NotConnected",
+    NetError::DnsTimedOut(_) => "TimedOut",
+    NetError::Dns(_) => "Error",
+    NetError::UnsupportedRecordType => "NotSupported",
+    NetError::InvalidUtf8(_) => "InvalidData",
+    NetError::UnexpectedKeyType => "Error",
+    NetError::InvalidHostname(_) => "TypeError",
+    NetError::TcpStreamBusy => "Busy",
+    NetError::Rustls(_) => "Error",
+    NetError::Tls(e) => get_tls_error_class(e),
+    NetError::ListenTlsRequiresKey => "InvalidData",
+    NetError::Reunite(_) => "Error",
+  }
+}
+
+fn get_net_map_error(error: &deno_net::io::MapError) -> &'static str {
+  match error {
+    deno_net::io::MapError::Io(e) => get_io_error_class(e),
+    deno_net::io::MapError::NoResources => "Error",
+  }
+}
+
+fn get_create_worker_error(error: &CreateWorkerError) -> &'static str {
+  match error {
+    CreateWorkerError::ClassicWorkers => "DOMExceptionNotSupportedError",
+    CreateWorkerError::Permission(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    CreateWorkerError::ModuleResolution(e) => {
+      get_module_resolution_error_class(e)
+    }
+    CreateWorkerError::Io(e) => get_io_error_class(e),
+    CreateWorkerError::MessagePort(e) => get_web_message_port_error_class(e),
+  }
+}
+
+fn get_tty_error(error: &TtyError) -> &'static str {
+  match error {
+    TtyError::Resource(e) | TtyError::Other(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    TtyError::Io(e) => get_io_error_class(e),
+    #[cfg(unix)]
+    TtyError::Nix(e) => get_nix_error_class(e),
+  }
+}
+
+fn get_readline_error(error: &ReadlineError) -> &'static str {
+  match error {
+    ReadlineError::Io(e) => get_io_error_class(e),
+    ReadlineError::Eof => "Error",
+    ReadlineError::Interrupted => "Error",
+    #[cfg(unix)]
+    ReadlineError::Errno(e) => get_nix_error_class(e),
+    ReadlineError::WindowResized => "Error",
+    #[cfg(windows)]
+    ReadlineError::Decode(_) => "Error",
+    #[cfg(windows)]
+    ReadlineError::SystemError(_) => "Error",
+    _ => "Error",
+  }
+}
+
+fn get_signal_error(error: &SignalError) -> &'static str {
+  match error {
+    SignalError::InvalidSignalStr(_) => "TypeError",
+    SignalError::InvalidSignalInt(_) => "TypeError",
+    SignalError::SignalNotAllowed(_) => "TypeError",
+    SignalError::Io(e) => get_io_error_class(e),
+  }
+}
+
+fn get_fs_events_error(error: &FsEventsError) -> &'static str {
+  match error {
+    FsEventsError::Resource(e) | FsEventsError::Permission(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    FsEventsError::Notify(e) => get_notify_error_class(e),
+    FsEventsError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+  }
+}
+
+fn get_http_start_error(error: &HttpStartError) -> &'static str {
+  match error {
+    HttpStartError::TcpStreamInUse => "Busy",
+    HttpStartError::TlsStreamInUse => "Busy",
+    HttpStartError::UnixSocketInUse => "Busy",
+    HttpStartError::ReuniteTcp(_) => "Error",
+    #[cfg(unix)]
+    HttpStartError::ReuniteUnix(_) => "Error",
+    HttpStartError::Io(e) => get_io_error_class(e),
+    HttpStartError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
+fn get_process_error(error: &ProcessError) -> &'static str {
+  match error {
+    ProcessError::SpawnFailed { error, .. } => get_process_error(error),
+    ProcessError::FailedResolvingCwd(e) | ProcessError::Io(e) => {
+      get_io_error_class(e)
+    }
+    ProcessError::Permission(e) | ProcessError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+    ProcessError::BorrowMut(_) => "Error",
+    ProcessError::Which(_) => "Error",
+    ProcessError::ChildProcessAlreadyTerminated => "TypeError",
+    ProcessError::Signal(e) => get_signal_error(e),
+    ProcessError::MissingCmd => "Error",
+    ProcessError::InvalidPid => "TypeError",
+    #[cfg(unix)]
+    ProcessError::Nix(e) => get_nix_error_class(e),
+  }
+}
+
+fn get_http_error(error: &HttpError) -> &'static str {
+  match error {
+    HttpError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    HttpError::HyperV014(e) => get_hyper_v014_error_class(e),
+    HttpError::InvalidHeaderName(_) => "Error",
+    HttpError::InvalidHeaderValue(_) => "Error",
+    HttpError::Http(_) => "Error",
+    HttpError::ResponseHeadersAlreadySent => "Http",
+    HttpError::ConnectionClosedWhileSendingResponse => "Http",
+    HttpError::AlreadyInUse => "Http",
+    HttpError::Io(e) => get_io_error_class(e),
+    HttpError::NoResponseHeaders => "Http",
+    HttpError::ResponseAlreadyCompleted => "Http",
+    HttpError::UpgradeBodyUsed => "Http",
+    HttpError::Resource(e) | HttpError::Other(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+  }
+}
+
+fn get_http_next_error(error: &HttpNextError) -> &'static str {
+  match error {
+    HttpNextError::Io(e) => get_io_error_class(e),
+    HttpNextError::WebSocketUpgrade(e) => get_websocket_upgrade_error(e),
+    HttpNextError::Hyper(e) => get_hyper_error_class(e),
+    HttpNextError::JoinError(_) => "Error",
+    HttpNextError::Canceled(e) => {
+      let io_err: io::Error = e.to_owned().into();
+      get_io_error_class(&io_err)
+    }
+    HttpNextError::UpgradeUnavailable(_) => "Error",
+    HttpNextError::HttpPropertyExtractor(e) | HttpNextError::Resource(e) => {
+      get_error_class_name(e).unwrap_or("Error")
+    }
+  }
+}
+
+fn get_websocket_upgrade_error(error: &WebSocketUpgradeError) -> &'static str {
+  match error {
+    WebSocketUpgradeError::InvalidHeaders => "Http",
+    WebSocketUpgradeError::HttpParse(_) => "Error",
+    WebSocketUpgradeError::Http(_) => "Error",
+    WebSocketUpgradeError::Utf8(_) => "Error",
+    WebSocketUpgradeError::InvalidHeaderName(_) => "Error",
+    WebSocketUpgradeError::InvalidHeaderValue(_) => "Error",
+    WebSocketUpgradeError::InvalidHttpStatusLine => "Http",
+    WebSocketUpgradeError::UpgradeBufferAlreadyCompleted => "Http",
+  }
+}
+
+fn get_fs_error(e: &FsError) -> &'static str {
+  match &e {
+    FsError::Io(e) => get_io_error_class(e),
+    FsError::FileBusy => "Busy",
+    FsError::NotSupported => "NotSupported",
+    FsError::NotCapable(_) => "NotCapable",
+  }
+}
+
+mod node {
+  use super::get_error_class_name;
+  use super::get_io_error_class;
+  use super::get_serde_json_error_class;
+  use super::get_url_parse_error_class;
+  pub use deno_node::ops::blocklist::BlocklistError;
+  pub use deno_node::ops::fs::FsError;
+  pub use deno_node::ops::http2::Http2Error;
+  pub use deno_node::ops::idna::IdnaError;
+  pub use deno_node::ops::ipc::IpcError;
+  pub use deno_node::ops::ipc::IpcJsonStreamError;
+  use deno_node::ops::os::priority::PriorityError;
+  pub use deno_node::ops::os::OsError;
+  pub use deno_node::ops::require::RequireError;
+  pub use deno_node::ops::worker_threads::WorkerThreadsFilenameError;
+  pub use deno_node::ops::zlib::brotli::BrotliError;
+  pub use deno_node::ops::zlib::mode::ModeError;
+  pub use deno_node::ops::zlib::ZlibError;
+
+  pub fn get_blocklist_error(error: &BlocklistError) -> &'static str {
+    match error {
+      BlocklistError::AddrParse(_) => "Error",
+      BlocklistError::IpNetwork(_) => "Error",
+      BlocklistError::InvalidAddress => "Error",
+      BlocklistError::IpVersionMismatch => "Error",
+    }
+  }
+
+  pub fn get_fs_error(error: &FsError) -> &'static str {
+    match error {
+      FsError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+      FsError::Io(e) => get_io_error_class(e),
+      #[cfg(windows)]
+      FsError::PathHasNoRoot => "Error",
+      #[cfg(not(any(unix, windows)))]
+      FsError::UnsupportedPlatform => "Error",
+      FsError::Fs(e) => super::get_fs_error(e),
+    }
+  }
+
+  pub fn get_idna_error(error: &IdnaError) -> &'static str {
+    match error {
+      IdnaError::InvalidInput => "RangeError",
+      IdnaError::InputTooLong => "Error",
+      IdnaError::IllegalInput => "RangeError",
+    }
+  }
+
+  pub fn get_ipc_json_stream_error(error: &IpcJsonStreamError) -> &'static str {
+    match error {
+      IpcJsonStreamError::Io(e) => get_io_error_class(e),
+      IpcJsonStreamError::SimdJson(_) => "Error",
+    }
+  }
+
+  pub fn get_ipc_error(error: &IpcError) -> &'static str {
+    match error {
+      IpcError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+      IpcError::IpcJsonStream(e) => get_ipc_json_stream_error(e),
+      IpcError::Canceled(e) => {
+        let io_err: std::io::Error = e.to_owned().into();
+        get_io_error_class(&io_err)
+      }
+      IpcError::SerdeJson(e) => get_serde_json_error_class(e),
+    }
+  }
+
+  pub fn get_worker_threads_filename_error(
+    error: &WorkerThreadsFilenameError,
+  ) -> &'static str {
+    match error {
+      WorkerThreadsFilenameError::Permission(e) => {
+        get_error_class_name(e).unwrap_or("Error")
+      }
+      WorkerThreadsFilenameError::UrlParse(e) => get_url_parse_error_class(e),
+      WorkerThreadsFilenameError::InvalidRelativeUrl => "Error",
+      WorkerThreadsFilenameError::UrlFromPathString => "Error",
+      WorkerThreadsFilenameError::UrlToPathString => "Error",
+      WorkerThreadsFilenameError::UrlToPath => "Error",
+      WorkerThreadsFilenameError::FileNotFound(_) => "Error",
+      WorkerThreadsFilenameError::Fs(e) => super::get_fs_error(e),
+    }
+  }
+
+  pub fn get_require_error(error: &RequireError) -> &'static str {
+    match error {
+      RequireError::UrlParse(e) => get_url_parse_error_class(e),
+      RequireError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+      RequireError::PackageExportsResolve(_)
+      | RequireError::PackageJsonLoad(_)
+      | RequireError::ClosestPkgJson(_)
+      | RequireError::FilePathConversion(_)
+      | RequireError::UrlConversion(_)
+      | RequireError::ReadModule(_)
+      | RequireError::PackageImportsResolve(_) => "Error",
+      RequireError::Fs(e) | RequireError::UnableToGetCwd(e) => {
+        super::get_fs_error(e)
+      }
+    }
+  }
+
+  pub fn get_http2_error(error: &Http2Error) -> &'static str {
+    match error {
+      Http2Error::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+      Http2Error::UrlParse(e) => get_url_parse_error_class(e),
+      Http2Error::H2(_) => "Error",
+    }
+  }
+
+  pub fn get_os_error(error: &OsError) -> &'static str {
+    match error {
+      OsError::Priority(e) => match e {
+        PriorityError::Io(e) => get_io_error_class(e),
+        #[cfg(windows)]
+        PriorityError::InvalidPriority => "TypeError",
+      },
+      OsError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+      OsError::FailedToGetCpuInfo => "TypeError",
+      OsError::FailedToGetUserInfo(e) => get_io_error_class(e),
+    }
+  }
+
+  pub fn get_brotli_error(error: &BrotliError) -> &'static str {
+    match error {
+      BrotliError::InvalidEncoderMode => "TypeError",
+      BrotliError::CompressFailed => "TypeError",
+      BrotliError::DecompressFailed => "TypeError",
+      BrotliError::Join(_) => "Error",
+      BrotliError::Resource(e) => get_error_class_name(e).unwrap_or("Error"),
+      BrotliError::Io(e) => get_io_error_class(e),
+    }
+  }
+
+  pub fn get_mode_error(_: &ModeError) -> &'static str {
+    "Error"
+  }
+
+  pub fn get_zlib_error(e: &ZlibError) -> &'static str {
+    match e {
+      ZlibError::NotInitialized => "TypeError",
+      ZlibError::Mode(e) => get_mode_error(e),
+      ZlibError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+    }
+  }
+}
+
+fn get_os_error(error: &OsError) -> &'static str {
+  match error {
+    OsError::Permission(e) => get_error_class_name(e).unwrap_or("Error"),
+    OsError::InvalidUtf8(_) => "InvalidData",
+    OsError::EnvEmptyKey => "TypeError",
+    OsError::EnvInvalidKey(_) => "TypeError",
+    OsError::EnvInvalidValue(_) => "TypeError",
+    OsError::Io(e) => get_io_error_class(e),
+    OsError::Var(e) => get_env_var_error_class(e),
+  }
+}
+
+fn get_sync_fetch_error(error: &SyncFetchError) -> &'static str {
+  match error {
+    SyncFetchError::BlobUrlsNotSupportedInContext => "TypeError",
+    SyncFetchError::Io(e) => get_io_error_class(e),
+    SyncFetchError::InvalidScriptUrl => "TypeError",
+    SyncFetchError::InvalidStatusCode(_) => "TypeError",
+    SyncFetchError::ClassicScriptSchemeUnsupportedInWorkers(_) => "TypeError",
+    SyncFetchError::InvalidUri(_) => "Error",
+    SyncFetchError::InvalidMimeType(_) => "DOMExceptionNetworkError",
+    SyncFetchError::MissingMimeType => "DOMExceptionNetworkError",
+    SyncFetchError::Fetch(e) => get_fetch_error(e),
+    SyncFetchError::Join(_) => "Error",
+    SyncFetchError::Other(e) => get_error_class_name(e).unwrap_or("Error"),
+  }
+}
+
 pub fn get_error_class_name(e: &AnyError) -> Option<&'static str> {
   deno_core::error::get_custom_error_class(e)
-    .or_else(|| deno_webgpu::error::get_error_class_name(e))
-    .or_else(|| deno_web::get_error_class_name(e))
-    .or_else(|| deno_webstorage::get_not_supported_error_class_name(e))
-    .or_else(|| deno_websocket::get_network_error_class_name(e))
+    .or_else(|| e.downcast_ref::<FsError>().map(get_fs_error))
+    .or_else(|| {
+      e.downcast_ref::<node::BlocklistError>()
+        .map(node::get_blocklist_error)
+    })
+    .or_else(|| e.downcast_ref::<node::FsError>().map(node::get_fs_error))
+    .or_else(|| {
+      e.downcast_ref::<node::IdnaError>()
+        .map(node::get_idna_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::IpcJsonStreamError>()
+        .map(node::get_ipc_json_stream_error)
+    })
+    .or_else(|| e.downcast_ref::<node::IpcError>().map(node::get_ipc_error))
+    .or_else(|| {
+      e.downcast_ref::<node::WorkerThreadsFilenameError>()
+        .map(node::get_worker_threads_filename_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::RequireError>()
+        .map(node::get_require_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::Http2Error>()
+        .map(node::get_http2_error)
+    })
+    .or_else(|| e.downcast_ref::<node::OsError>().map(node::get_os_error))
+    .or_else(|| {
+      e.downcast_ref::<node::BrotliError>()
+        .map(node::get_brotli_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::ModeError>()
+        .map(node::get_mode_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<node::ZlibError>()
+        .map(node::get_zlib_error)
+    })
+    .or_else(|| e.downcast_ref::<NApiError>().map(get_napi_error_class))
+    .or_else(|| e.downcast_ref::<WebError>().map(get_web_error_class))
+    .or_else(|| {
+      e.downcast_ref::<CreateWorkerError>()
+        .map(get_create_worker_error)
+    })
+    .or_else(|| e.downcast_ref::<TtyError>().map(get_tty_error))
+    .or_else(|| e.downcast_ref::<ReadlineError>().map(get_readline_error))
+    .or_else(|| e.downcast_ref::<SignalError>().map(get_signal_error))
+    .or_else(|| e.downcast_ref::<FsEventsError>().map(get_fs_events_error))
+    .or_else(|| e.downcast_ref::<HttpStartError>().map(get_http_start_error))
+    .or_else(|| e.downcast_ref::<ProcessError>().map(get_process_error))
+    .or_else(|| e.downcast_ref::<OsError>().map(get_os_error))
+    .or_else(|| e.downcast_ref::<SyncFetchError>().map(get_sync_fetch_error))
+    .or_else(|| {
+      e.downcast_ref::<CompressionError>()
+        .map(get_web_compression_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<MessagePortError>()
+        .map(get_web_message_port_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<StreamResourceError>()
+        .map(get_web_stream_resource_error_class)
+    })
+    .or_else(|| e.downcast_ref::<BlobError>().map(get_web_blob_error_class))
+    .or_else(|| e.downcast_ref::<IRError>().map(|_| "TypeError"))
+    .or_else(|| e.downcast_ref::<ReprError>().map(get_ffi_repr_error_class))
+    .or_else(|| e.downcast_ref::<HttpError>().map(get_http_error))
+    .or_else(|| e.downcast_ref::<HttpNextError>().map(get_http_next_error))
+    .or_else(|| {
+      e.downcast_ref::<WebSocketUpgradeError>()
+        .map(get_websocket_upgrade_error)
+    })
+    .or_else(|| e.downcast_ref::<FsOpsError>().map(get_fs_ops_error))
+    .or_else(|| {
+      e.downcast_ref::<DlfcnError>()
+        .map(get_ffi_dlfcn_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<StaticError>()
+        .map(get_ffi_static_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<CallbackError>()
+        .map(get_ffi_callback_error_class)
+    })
+    .or_else(|| e.downcast_ref::<CallError>().map(get_ffi_call_error_class))
+    .or_else(|| e.downcast_ref::<TlsError>().map(get_tls_error_class))
+    .or_else(|| e.downcast_ref::<CronError>().map(get_cron_error_class))
+    .or_else(|| e.downcast_ref::<CanvasError>().map(get_canvas_error))
+    .or_else(|| e.downcast_ref::<CacheError>().map(get_cache_error))
+    .or_else(|| e.downcast_ref::<WebsocketError>().map(get_websocket_error))
+    .or_else(|| {
+      e.downcast_ref::<HandshakeError>()
+        .map(get_websocket_handshake_error)
+    })
+    .or_else(|| e.downcast_ref::<KvError>().map(get_kv_error))
+    .or_else(|| e.downcast_ref::<FetchError>().map(get_fetch_error))
+    .or_else(|| {
+      e.downcast_ref::<HttpClientCreateError>()
+        .map(get_http_client_create_error)
+    })
+    .or_else(|| e.downcast_ref::<NetError>().map(get_net_error))
+    .or_else(|| {
+      e.downcast_ref::<deno_net::io::MapError>()
+        .map(get_net_map_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<BroadcastChannelError>()
+        .map(get_broadcast_channel_error)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::InitError>()
+        .map(get_webgpu_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::buffer::BufferError>()
+        .map(get_webgpu_buffer_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::bundle::BundleError>()
+        .map(get_webgpu_bundle_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::byow::ByowError>()
+        .map(get_webgpu_byow_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::render_pass::RenderPassError>()
+        .map(get_webgpu_render_pass_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_webgpu::surface::SurfaceError>()
+        .map(get_webgpu_surface_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<DecryptError>()
+        .map(get_crypto_decrypt_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<EncryptError>()
+        .map(get_crypto_encrypt_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::SharedError>()
+        .map(get_crypto_shared_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::Ed25519Error>()
+        .map(get_crypto_ed25519_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<ExportKeyError>()
+        .map(get_crypto_export_key_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<GenerateKeyError>()
+        .map(get_crypto_generate_key_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<ImportKeyError>()
+        .map(get_crypto_import_key_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::X448Error>()
+        .map(get_crypto_x448_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::X25519Error>()
+        .map(get_crypto_x25519_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_crypto::Error>()
+        .map(get_crypto_error_class)
+    })
+    .or_else(|| {
+      e.downcast_ref::<WebStorageError>()
+        .map(get_webstorage_class_name)
+    })
+    .or_else(|| {
+      e.downcast_ref::<deno_url::UrlPatternError>()
+        .map(|_| "TypeError")
+    })
     .or_else(|| {
       e.downcast_ref::<dlopen2::Error>()
         .map(get_dlopen_error_class)
diff --git a/runtime/fmt_errors.rs b/runtime/fmt_errors.rs
index 44a9477327..4cd8a06345 100644
--- a/runtime/fmt_errors.rs
+++ b/runtime/fmt_errors.rs
@@ -1,11 +1,10 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 //! This mod provides DenoError to unify errors across Deno.
+use color_print::cformat;
+use color_print::cstr;
 use deno_core::error::format_frame;
 use deno_core::error::JsError;
-use deno_terminal::colors::cyan;
-use deno_terminal::colors::italic_bold;
-use deno_terminal::colors::red;
-use deno_terminal::colors::yellow;
+use deno_terminal::colors;
 use std::fmt::Write as _;
 
 #[derive(Debug, Clone)]
@@ -24,6 +23,7 @@ struct IndexedErrorReference<'a> {
 enum FixSuggestionKind {
   Info,
   Hint,
+  Docs,
 }
 
 #[derive(Debug)]
@@ -66,6 +66,13 @@ impl<'a> FixSuggestion<'a> {
       message: FixSuggestionMessage::Multiline(messages),
     }
   }
+
+  pub fn docs(url: &'a str) -> Self {
+    Self {
+      kind: FixSuggestionKind::Docs,
+      message: FixSuggestionMessage::Single(url),
+    }
+  }
 }
 
 struct AnsiColors;
@@ -78,10 +85,10 @@ impl deno_core::error::ErrorFormat for AnsiColors {
     use deno_core::error::ErrorElement::*;
     match element {
       Anonymous | NativeFrame | FileName | EvalOrigin => {
-        cyan(s).to_string().into()
+        colors::cyan(s).to_string().into()
       }
-      LineNumber | ColumnNumber => yellow(s).to_string().into(),
-      FunctionName | PromiseAll => italic_bold(s).to_string().into(),
+      LineNumber | ColumnNumber => colors::yellow(s).to_string().into(),
+      FunctionName | PromiseAll => colors::italic_bold(s).to_string().into(),
     }
   }
 }
@@ -114,7 +121,7 @@ fn format_maybe_source_line(
   if column_number as usize > source_line.len() {
     return format!(
       "\n{} Couldn't format source line: Column {} is out of bounds (source may have changed at runtime)",
-      yellow("Warning"), column_number,
+      colors::yellow("Warning"), column_number,
     );
   }
 
@@ -127,9 +134,9 @@ fn format_maybe_source_line(
   }
   s.push('^');
   let color_underline = if is_error {
-    red(&s).to_string()
+    colors::red(&s).to_string()
   } else {
-    cyan(&s).to_string()
+    colors::cyan(&s).to_string()
   };
 
   let indent = format!("{:indent$}", "", indent = level);
@@ -200,7 +207,8 @@ fn format_js_error_inner(
 
   if let Some(circular) = &circular {
     if js_error.is_same_error(circular.reference.to) {
-      write!(s, " {}", cyan(format!("<ref *{}>", circular.index))).unwrap();
+      write!(s, " {}", colors::cyan(format!("<ref *{}>", circular.index)))
+        .unwrap();
     }
   }
 
@@ -238,7 +246,8 @@ fn format_js_error_inner(
       .unwrap_or(false);
 
     let error_string = if is_caused_by_circular {
-      cyan(format!("[Circular *{}]", circular.unwrap().index)).to_string()
+      colors::cyan(format!("[Circular *{}]", circular.unwrap().index))
+        .to_string()
     } else {
       format_js_error_inner(cause, circular, false, vec![])
     };
@@ -255,12 +264,23 @@ fn format_js_error_inner(
     for (index, suggestion) in suggestions.iter().enumerate() {
       write!(s, "    ").unwrap();
       match suggestion.kind {
-        FixSuggestionKind::Hint => write!(s, "{} ", cyan("hint:")).unwrap(),
-        FixSuggestionKind::Info => write!(s, "{} ", yellow("info:")).unwrap(),
+        FixSuggestionKind::Hint => {
+          write!(s, "{} ", colors::cyan("hint:")).unwrap()
+        }
+        FixSuggestionKind::Info => {
+          write!(s, "{} ", colors::yellow("info:")).unwrap()
+        }
+        FixSuggestionKind::Docs => {
+          write!(s, "{} ", colors::green("docs:")).unwrap()
+        }
       };
       match suggestion.message {
         FixSuggestionMessage::Single(msg) => {
-          write!(s, "{}", msg).unwrap();
+          if matches!(suggestion.kind, FixSuggestionKind::Docs) {
+            write!(s, "{}", cformat!("<u>{}</>", msg)).unwrap();
+          } else {
+            write!(s, "{}", msg).unwrap();
+          }
         }
         FixSuggestionMessage::Multiline(messages) => {
           for (idx, message) in messages.iter().enumerate() {
@@ -282,6 +302,155 @@ fn format_js_error_inner(
   s
 }
 
+fn get_suggestions_for_terminal_errors(e: &JsError) -> Vec<FixSuggestion> {
+  if let Some(msg) = &e.message {
+    if msg.contains("module is not defined")
+      || msg.contains("exports is not defined")
+      || msg.contains("require is not defined")
+    {
+      return vec![
+        FixSuggestion::info_multiline(&[
+          cstr!("Deno supports CommonJS modules in <u>.cjs</> files, or when there's a <u>package.json</>"),
+          cstr!("with <i>\"type\": \"commonjs\"</> option and <i>--unstable-detect-cjs</> flag is used.")
+        ]),
+        FixSuggestion::hint_multiline(&[
+          "Rewrite this module to ESM,",
+          cstr!("or change the file extension to <u>.cjs</u>,"),
+          cstr!("or add <u>package.json</> next to the file with <i>\"type\": \"commonjs\"</> option"),
+          cstr!("and pass <i>--unstable-detect-cjs</> flag."),
+        ]),
+        FixSuggestion::docs("https://docs.deno.com/go/commonjs"),
+      ];
+    } else if msg.contains("__filename is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>__filename</> global is not available in ES modules."
+        )),
+        FixSuggestion::hint(cstr!("Use <u>import.meta.filename</> instead.")),
+      ];
+    } else if msg.contains("__dirname is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>__dirname</> global is not available in ES modules."
+        )),
+        FixSuggestion::hint(cstr!("Use <u>import.meta.dirname</> instead.")),
+      ];
+    } else if msg.contains("Buffer is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>Buffer</> is not available in the global scope in Deno."
+        )),
+        FixSuggestion::hint(cstr!("Import it explicitly with <u>import { Buffer } from \"node:buffer\";</>.")),
+      ];
+    } else if msg.contains("clearImmediate is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>clearImmediate</> is not available in the global scope in Deno."
+        )),
+        FixSuggestion::hint(cstr!("Import it explicitly with <u>import { clearImmediate } from \"node:timers\";</>.")),
+      ];
+    } else if msg.contains("setImmediate is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>setImmediate</> is not available in the global scope in Deno."
+        )),
+        FixSuggestion::hint(cstr!("Import it explicitly with <u>import { setImmediate } from \"node:timers\";</>.")),
+      ];
+    } else if msg.contains("global is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>global</> is not available in the global scope in Deno."
+        )),
+        FixSuggestion::hint(cstr!("Use <u>globalThis</> instead, or assign <u>globalThis.global = globalThis</>.")),
+      ];
+    } else if msg.contains("openKv is not a function") {
+      return vec![
+        FixSuggestion::info("Deno.openKv() is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-kv` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("cron is not a function") {
+      return vec![
+        FixSuggestion::info("Deno.cron() is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-cron` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("WebSocketStream is not defined") {
+      return vec![
+        FixSuggestion::info("new WebSocketStream() is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-net` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("Temporal is not defined") {
+      return vec![
+        FixSuggestion::info("Temporal is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-temporal` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("BroadcastChannel is not defined") {
+      return vec![
+        FixSuggestion::info("BroadcastChannel is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-broadcast-channel` flag to enable this API.",
+        ),
+      ];
+    } else if msg.contains("window is not defined") {
+      return vec![
+        FixSuggestion::info("window global is not available in Deno 2."),
+        FixSuggestion::hint("Replace `window` with `globalThis`."),
+      ];
+    } else if msg.contains("UnsafeWindowSurface is not a constructor") {
+      return vec![
+        FixSuggestion::info("Deno.UnsafeWindowSurface is an unstable API."),
+        FixSuggestion::hint(
+          "Run again with `--unstable-webgpu` flag to enable this API.",
+        ),
+      ];
+    // Try to capture errors like:
+    // ```
+    // Uncaught Error: Cannot find module '../build/Release/canvas.node'
+    // Require stack:
+    // - /.../deno/npm/registry.npmjs.org/canvas/2.11.2/lib/bindings.js
+    // - /.../.cache/deno/npm/registry.npmjs.org/canvas/2.11.2/lib/canvas.js
+    // ```
+    } else if msg.contains("Cannot find module")
+      && msg.contains("Require stack")
+      && msg.contains(".node'")
+    {
+      return vec![
+        FixSuggestion::info_multiline(
+          &[
+            "Trying to execute an npm package using Node-API addons,",
+            "these packages require local `node_modules` directory to be present."
+          ]
+        ),
+        FixSuggestion::hint_multiline(
+          &[
+            "Add `\"nodeModulesDir\": \"auto\" option to `deno.json`, and then run",
+            "`deno install --allow-scripts=npm:<package> --entrypoint <script>` to setup `node_modules` directory."
+          ]
+        )
+      ];
+    } else if msg.contains("document is not defined") {
+      return vec![
+        FixSuggestion::info(cstr!(
+          "<u>document</> global is not available in Deno."
+        )),
+        FixSuggestion::hint_multiline(&[
+          cstr!("Use a library like <u>happy-dom</>, <u>deno_dom</>, <u>linkedom</> or <u>JSDom</>"),
+          cstr!("and setup the <u>document</> global according to the library documentation."),
+        ]),
+      ];
+    }
+  }
+
+  vec![]
+}
+
 /// Format a [`JsError`] for terminal output.
 pub fn format_js_error(js_error: &JsError) -> String {
   let circular =
@@ -289,21 +458,7 @@ pub fn format_js_error(js_error: &JsError) -> String {
       reference,
       index: 1,
     });
-
-  format_js_error_inner(js_error, circular, true, vec![])
-}
-
-/// Format a [`JsError`] for terminal output, printing additional suggestions.
-pub fn format_js_error_with_suggestions(
-  js_error: &JsError,
-  suggestions: Vec<FixSuggestion>,
-) -> String {
-  let circular =
-    find_recursive_cause(js_error).map(|reference| IndexedErrorReference {
-      reference,
-      index: 1,
-    });
-
+  let suggestions = get_suggestions_for_terminal_errors(js_error);
   format_js_error_inner(js_error, circular, true, suggestions)
 }
 
diff --git a/runtime/inspector_server.rs b/runtime/inspector_server.rs
index 1f8cd5e714..a789dd3dca 100644
--- a/runtime/inspector_server.rs
+++ b/runtime/inspector_server.rs
@@ -19,6 +19,8 @@ use deno_core::serde_json::Value;
 use deno_core::unsync::spawn;
 use deno_core::url::Url;
 use deno_core::InspectorMsg;
+use deno_core::InspectorSessionKind;
+use deno_core::InspectorSessionOptions;
 use deno_core::InspectorSessionProxy;
 use deno_core::JsRuntime;
 use fastwebsockets::Frame;
@@ -192,6 +194,11 @@ fn handle_ws_request(
     let inspector_session_proxy = InspectorSessionProxy {
       tx: outbound_tx,
       rx: inbound_rx,
+      options: InspectorSessionOptions {
+        kind: InspectorSessionKind::NonBlocking {
+          wait_for_disconnect: true,
+        },
+      },
     };
 
     log::info!("Debugger session started.");
diff --git a/runtime/js/10_permissions.js b/runtime/js/10_permissions.js
index ef31358687..831b6bf2ae 100644
--- a/runtime/js/10_permissions.js
+++ b/runtime/js/10_permissions.js
@@ -269,7 +269,13 @@ function serializePermissions(permissions) {
   if (typeof permissions == "object" && permissions != null) {
     const serializedPermissions = { __proto__: null };
     for (
-      const key of new SafeArrayIterator(["read", "write", "run", "ffi"])
+      const key of new SafeArrayIterator([
+        "read",
+        "write",
+        "run",
+        "ffi",
+        "import",
+      ])
     ) {
       if (ArrayIsArray(permissions[key])) {
         serializedPermissions[key] = ArrayPrototypeMap(
diff --git a/runtime/js/40_fs_events.js b/runtime/js/40_fs_events.js
index ec2474c0ad..322ee6b3ca 100644
--- a/runtime/js/40_fs_events.js
+++ b/runtime/js/40_fs_events.js
@@ -21,7 +21,7 @@ class FsWatcher {
 
   constructor(paths, options) {
     const { recursive } = options;
-    this.#rid = op_fs_events_open({ recursive, paths });
+    this.#rid = op_fs_events_open(recursive, paths);
   }
 
   unref() {
diff --git a/runtime/ops/fs_events.rs b/runtime/ops/fs_events.rs
index d88a32d917..648553376a 100644
--- a/runtime/ops/fs_events.rs
+++ b/runtime/ops/fs_events.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::parking_lot::Mutex;
 use deno_core::AsyncRefCell;
 use deno_core::CancelFuture;
@@ -20,13 +19,14 @@ use notify::EventKind;
 use notify::RecommendedWatcher;
 use notify::RecursiveMode;
 use notify::Watcher;
-use serde::Deserialize;
 use serde::Serialize;
 use std::borrow::Cow;
 use std::cell::RefCell;
 use std::convert::From;
+use std::path::Path;
 use std::path::PathBuf;
 use std::rc::Rc;
+use std::sync::Arc;
 use tokio::sync::mpsc;
 
 deno_core::extension!(
@@ -35,9 +35,7 @@ deno_core::extension!(
 );
 
 struct FsEventsResource {
-  #[allow(unused)]
-  watcher: RecommendedWatcher,
-  receiver: AsyncRefCell<mpsc::Receiver<Result<FsEvent, AnyError>>>,
+  receiver: AsyncRefCell<mpsc::Receiver<Result<FsEvent, NotifyError>>>,
   cancel: CancelHandle,
 }
 
@@ -59,7 +57,7 @@ impl Resource for FsEventsResource {
 ///
 /// Feel free to expand this struct as long as you can add tests to demonstrate
 /// the complexity.
-#[derive(Serialize, Debug)]
+#[derive(Serialize, Debug, Clone)]
 struct FsEvent {
   kind: &'static str,
   paths: Vec<PathBuf>,
@@ -93,43 +91,103 @@ impl From<NotifyEvent> for FsEvent {
   }
 }
 
-#[derive(Deserialize)]
-pub struct OpenArgs {
-  recursive: bool,
+type WatchSender = (Vec<String>, mpsc::Sender<Result<FsEvent, NotifyError>>);
+
+struct WatcherState {
+  senders: Arc<Mutex<Vec<WatchSender>>>,
+  watcher: RecommendedWatcher,
+}
+
+fn starts_with_canonicalized(path: &Path, prefix: &str) -> bool {
+  #[allow(clippy::disallowed_methods)]
+  let path = path.canonicalize().ok();
+  #[allow(clippy::disallowed_methods)]
+  let prefix = std::fs::canonicalize(prefix).ok();
+  match (path, prefix) {
+    (Some(path), Some(prefix)) => path.starts_with(prefix),
+    _ => false,
+  }
+}
+
+#[derive(Debug, thiserror::Error)]
+pub enum FsEventsError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  Notify(#[from] NotifyError),
+  #[error(transparent)]
+  Canceled(#[from] deno_core::Canceled),
+}
+
+fn start_watcher(
+  state: &mut OpState,
   paths: Vec<String>,
+  sender: mpsc::Sender<Result<FsEvent, NotifyError>>,
+) -> Result<(), FsEventsError> {
+  if let Some(watcher) = state.try_borrow_mut::<WatcherState>() {
+    watcher.senders.lock().push((paths, sender));
+    return Ok(());
+  }
+
+  let senders = Arc::new(Mutex::new(vec![(paths, sender)]));
+
+  let sender_clone = senders.clone();
+  let watcher: RecommendedWatcher = Watcher::new(
+    move |res: Result<NotifyEvent, NotifyError>| {
+      let res2 = res.map(FsEvent::from).map_err(FsEventsError::Notify);
+      for (paths, sender) in sender_clone.lock().iter() {
+        // Ignore result, if send failed it means that watcher was already closed,
+        // but not all messages have been flushed.
+
+        // Only send the event if the path matches one of the paths that the user is watching
+        if let Ok(event) = &res2 {
+          if paths.iter().any(|path| {
+            event.paths.iter().any(|event_path| {
+              same_file::is_same_file(event_path, path).unwrap_or(false)
+                || starts_with_canonicalized(event_path, path)
+            })
+          }) {
+            let _ = sender.try_send(Ok(event.clone()));
+          }
+        }
+      }
+    },
+    Default::default(),
+  )?;
+
+  state.put::<WatcherState>(WatcherState { watcher, senders });
+
+  Ok(())
 }
 
 #[op2]
 #[smi]
 fn op_fs_events_open(
   state: &mut OpState,
-  #[serde] args: OpenArgs,
-) -> Result<ResourceId, AnyError> {
-  let (sender, receiver) = mpsc::channel::<Result<FsEvent, AnyError>>(16);
-  let sender = Mutex::new(sender);
-  let mut watcher: RecommendedWatcher = Watcher::new(
-    move |res: Result<NotifyEvent, NotifyError>| {
-      let res2 = res.map(FsEvent::from).map_err(AnyError::from);
-      let sender = sender.lock();
-      // Ignore result, if send failed it means that watcher was already closed,
-      // but not all messages have been flushed.
-      let _ = sender.try_send(res2);
-    },
-    Default::default(),
-  )?;
-  let recursive_mode = if args.recursive {
+  recursive: bool,
+  #[serde] paths: Vec<String>,
+) -> Result<ResourceId, FsEventsError> {
+  let (sender, receiver) = mpsc::channel::<Result<FsEvent, NotifyError>>(16);
+
+  start_watcher(state, paths.clone(), sender)?;
+
+  let recursive_mode = if recursive {
     RecursiveMode::Recursive
   } else {
     RecursiveMode::NonRecursive
   };
-  for path in &args.paths {
+  for path in &paths {
     let path = state
       .borrow_mut::<PermissionsContainer>()
-      .check_read(path, "Deno.watchFs()")?;
-    watcher.watch(&path, recursive_mode)?;
+      .check_read(path, "Deno.watchFs()")
+      .map_err(FsEventsError::Permission)?;
+
+    let watcher = state.borrow_mut::<WatcherState>();
+    watcher.watcher.watch(&path, recursive_mode)?;
   }
   let resource = FsEventsResource {
-    watcher,
     receiver: AsyncRefCell::new(receiver),
     cancel: Default::default(),
   };
@@ -142,14 +200,18 @@ fn op_fs_events_open(
 async fn op_fs_events_poll(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<Option<FsEvent>, AnyError> {
-  let resource = state.borrow().resource_table.get::<FsEventsResource>(rid)?;
+) -> Result<Option<FsEvent>, FsEventsError> {
+  let resource = state
+    .borrow()
+    .resource_table
+    .get::<FsEventsResource>(rid)
+    .map_err(FsEventsError::Resource)?;
   let mut receiver = RcRef::map(&resource, |r| &r.receiver).borrow_mut().await;
   let cancel = RcRef::map(resource, |r| &r.cancel);
   let maybe_result = receiver.recv().or_cancel(cancel).await?;
   match maybe_result {
     Some(Ok(value)) => Ok(Some(value)),
-    Some(Err(err)) => Err(err),
+    Some(Err(err)) => Err(FsEventsError::Notify(err)),
     None => Ok(None),
   }
 }
diff --git a/runtime/ops/http.rs b/runtime/ops/http.rs
index cec8b0ef8f..6e31576686 100644
--- a/runtime/ops/http.rs
+++ b/runtime/ops/http.rs
@@ -2,9 +2,6 @@
 
 use std::rc::Rc;
 
-use deno_core::error::bad_resource_id;
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use deno_core::ResourceId;
@@ -16,12 +13,31 @@ pub const UNSTABLE_FEATURE_NAME: &str = "http";
 
 deno_core::extension!(deno_http_runtime, ops = [op_http_start],);
 
+#[derive(Debug, thiserror::Error)]
+pub enum HttpStartError {
+  #[error("TCP stream is currently in use")]
+  TcpStreamInUse,
+  #[error("TLS stream is currently in use")]
+  TlsStreamInUse,
+  #[error("Unix socket is currently in use")]
+  UnixSocketInUse,
+  #[error(transparent)]
+  ReuniteTcp(#[from] tokio::net::tcp::ReuniteError),
+  #[cfg(unix)]
+  #[error(transparent)]
+  ReuniteUnix(#[from] tokio::net::unix::ReuniteError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[op2(fast)]
 #[smi]
 fn op_http_start(
   state: &mut OpState,
   #[smi] tcp_stream_rid: ResourceId,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, HttpStartError> {
   if let Ok(resource_rc) = state
     .resource_table
     .take::<TcpStreamResource>(tcp_stream_rid)
@@ -30,11 +46,11 @@ fn op_http_start(
     // process of starting a HTTP server on top of this TCP connection, so we just return a Busy error.
     // See also: https://github.com/denoland/deno/pull/16242
     let resource = Rc::try_unwrap(resource_rc)
-      .map_err(|_| custom_error("Busy", "TCP stream is currently in use"))?;
+      .map_err(|_| HttpStartError::TcpStreamInUse)?;
     let (read_half, write_half) = resource.into_inner();
     let tcp_stream = read_half.reunite(write_half)?;
     let addr = tcp_stream.local_addr()?;
-    return http_create_conn_resource(state, tcp_stream, addr, "http");
+    return Ok(http_create_conn_resource(state, tcp_stream, addr, "http"));
   }
 
   if let Ok(resource_rc) = state
@@ -45,11 +61,11 @@ fn op_http_start(
     // process of starting a HTTP server on top of this TLS connection, so we just return a Busy error.
     // See also: https://github.com/denoland/deno/pull/16242
     let resource = Rc::try_unwrap(resource_rc)
-      .map_err(|_| custom_error("Busy", "TLS stream is currently in use"))?;
+      .map_err(|_| HttpStartError::TlsStreamInUse)?;
     let (read_half, write_half) = resource.into_inner();
     let tls_stream = read_half.unsplit(write_half);
     let addr = tls_stream.local_addr()?;
-    return http_create_conn_resource(state, tls_stream, addr, "https");
+    return Ok(http_create_conn_resource(state, tls_stream, addr, "https"));
   }
 
   #[cfg(unix)]
@@ -61,12 +77,17 @@ fn op_http_start(
     // process of starting a HTTP server on top of this UNIX socket, so we just return a Busy error.
     // See also: https://github.com/denoland/deno/pull/16242
     let resource = Rc::try_unwrap(resource_rc)
-      .map_err(|_| custom_error("Busy", "Unix socket is currently in use"))?;
+      .map_err(|_| HttpStartError::UnixSocketInUse)?;
     let (read_half, write_half) = resource.into_inner();
     let unix_stream = read_half.reunite(write_half)?;
     let addr = unix_stream.local_addr()?;
-    return http_create_conn_resource(state, unix_stream, addr, "http+unix");
+    return Ok(http_create_conn_resource(
+      state,
+      unix_stream,
+      addr,
+      "http+unix",
+    ));
   }
 
-  Err(bad_resource_id())
+  Err(HttpStartError::Other(deno_core::error::bad_resource_id()))
 }
diff --git a/runtime/ops/mod.rs b/runtime/ops/mod.rs
index feed5052bb..67065b901b 100644
--- a/runtime/ops/mod.rs
+++ b/runtime/ops/mod.rs
@@ -9,7 +9,6 @@ pub mod process;
 pub mod runtime;
 pub mod signal;
 pub mod tty;
-mod utils;
 pub mod web_worker;
 pub mod worker_host;
 
diff --git a/runtime/ops/os/mod.rs b/runtime/ops/os/mod.rs
index bd9260e97e..24b0389e16 100644
--- a/runtime/ops/os/mod.rs
+++ b/runtime/ops/os/mod.rs
@@ -1,9 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use super::utils::into_string;
 use crate::worker::ExitCode;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::v8;
 use deno_core::OpState;
@@ -73,17 +70,39 @@ deno_core::extension!(
   },
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum OsError {
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error("File name or path {0:?} is not valid UTF-8")]
+  InvalidUtf8(std::ffi::OsString),
+  #[error("Key is an empty string.")]
+  EnvEmptyKey,
+  #[error("Key contains invalid characters: {0:?}")]
+  EnvInvalidKey(String),
+  #[error("Value contains invalid characters: {0:?}")]
+  EnvInvalidValue(String),
+  #[error(transparent)]
+  Var(#[from] env::VarError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+}
+
 #[op2]
 #[string]
-fn op_exec_path(state: &mut OpState) -> Result<String, AnyError> {
+fn op_exec_path(state: &mut OpState) -> Result<String, OsError> {
   let current_exe = env::current_exe().unwrap();
   state
     .borrow_mut::<PermissionsContainer>()
-    .check_read_blind(&current_exe, "exec_path", "Deno.execPath()")?;
+    .check_read_blind(&current_exe, "exec_path", "Deno.execPath()")
+    .map_err(OsError::Permission)?;
   // normalize path so it doesn't include '.' or '..' components
   let path = normalize_path(current_exe);
 
-  into_string(path.into_os_string())
+  path
+    .into_os_string()
+    .into_string()
+    .map_err(OsError::InvalidUtf8)
 }
 
 #[op2(fast)]
@@ -91,20 +110,19 @@ fn op_set_env(
   state: &mut OpState,
   #[string] key: &str,
   #[string] value: &str,
-) -> Result<(), AnyError> {
-  state.borrow_mut::<PermissionsContainer>().check_env(key)?;
+) -> Result<(), OsError> {
+  state
+    .borrow_mut::<PermissionsContainer>()
+    .check_env(key)
+    .map_err(OsError::Permission)?;
   if key.is_empty() {
-    return Err(type_error("Key is an empty string."));
+    return Err(OsError::EnvEmptyKey);
   }
   if key.contains(&['=', '\0'] as &[char]) {
-    return Err(type_error(format!(
-      "Key contains invalid characters: {key:?}"
-    )));
+    return Err(OsError::EnvInvalidKey(key.to_string()));
   }
   if value.contains('\0') {
-    return Err(type_error(format!(
-      "Value contains invalid characters: {value:?}"
-    )));
+    return Err(OsError::EnvInvalidValue(value.to_string()));
   }
   env::set_var(key, value);
   Ok(())
@@ -112,7 +130,9 @@ fn op_set_env(
 
 #[op2]
 #[serde]
-fn op_env(state: &mut OpState) -> Result<HashMap<String, String>, AnyError> {
+fn op_env(
+  state: &mut OpState,
+) -> Result<HashMap<String, String>, deno_core::error::AnyError> {
   state.borrow_mut::<PermissionsContainer>().check_env_all()?;
   Ok(env::vars().collect())
 }
@@ -122,21 +142,22 @@ fn op_env(state: &mut OpState) -> Result<HashMap<String, String>, AnyError> {
 fn op_get_env(
   state: &mut OpState,
   #[string] key: String,
-) -> Result<Option<String>, AnyError> {
+) -> Result<Option<String>, OsError> {
   let skip_permission_check = NODE_ENV_VAR_ALLOWLIST.contains(&key);
 
   if !skip_permission_check {
-    state.borrow_mut::<PermissionsContainer>().check_env(&key)?;
+    state
+      .borrow_mut::<PermissionsContainer>()
+      .check_env(&key)
+      .map_err(OsError::Permission)?;
   }
 
   if key.is_empty() {
-    return Err(type_error("Key is an empty string."));
+    return Err(OsError::EnvEmptyKey);
   }
 
   if key.contains(&['=', '\0'] as &[char]) {
-    return Err(type_error(format!(
-      "Key contains invalid characters: {key:?}"
-    )));
+    return Err(OsError::EnvInvalidKey(key.to_string()));
   }
 
   let r = match env::var(key) {
@@ -150,10 +171,13 @@ fn op_get_env(
 fn op_delete_env(
   state: &mut OpState,
   #[string] key: String,
-) -> Result<(), AnyError> {
-  state.borrow_mut::<PermissionsContainer>().check_env(&key)?;
+) -> Result<(), OsError> {
+  state
+    .borrow_mut::<PermissionsContainer>()
+    .check_env(&key)
+    .map_err(OsError::Permission)?;
   if key.is_empty() || key.contains(&['=', '\0'] as &[char]) {
-    return Err(type_error("Key contains invalid characters."));
+    return Err(OsError::EnvInvalidKey(key.to_string()));
   }
   env::remove_var(key);
   Ok(())
@@ -178,7 +202,9 @@ fn op_exit(state: &mut OpState) {
 
 #[op2]
 #[serde]
-fn op_loadavg(state: &mut OpState) -> Result<(f64, f64, f64), AnyError> {
+fn op_loadavg(
+  state: &mut OpState,
+) -> Result<(f64, f64, f64), deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("loadavg", "Deno.loadavg()")?;
@@ -187,7 +213,9 @@ fn op_loadavg(state: &mut OpState) -> Result<(f64, f64, f64), AnyError> {
 
 #[op2]
 #[string]
-fn op_hostname(state: &mut OpState) -> Result<String, AnyError> {
+fn op_hostname(
+  state: &mut OpState,
+) -> Result<String, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("hostname", "Deno.hostname()")?;
@@ -196,7 +224,9 @@ fn op_hostname(state: &mut OpState) -> Result<String, AnyError> {
 
 #[op2]
 #[string]
-fn op_os_release(state: &mut OpState) -> Result<String, AnyError> {
+fn op_os_release(
+  state: &mut OpState,
+) -> Result<String, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("osRelease", "Deno.osRelease()")?;
@@ -207,10 +237,11 @@ fn op_os_release(state: &mut OpState) -> Result<String, AnyError> {
 #[serde]
 fn op_network_interfaces(
   state: &mut OpState,
-) -> Result<Vec<NetworkInterface>, AnyError> {
+) -> Result<Vec<NetworkInterface>, OsError> {
   state
     .borrow_mut::<PermissionsContainer>()
-    .check_sys("networkInterfaces", "Deno.networkInterfaces()")?;
+    .check_sys("networkInterfaces", "Deno.networkInterfaces()")
+    .map_err(OsError::Permission)?;
   Ok(netif::up()?.map(NetworkInterface::from).collect())
 }
 
@@ -259,7 +290,7 @@ impl From<netif::Interface> for NetworkInterface {
 #[serde]
 fn op_system_memory_info(
   state: &mut OpState,
-) -> Result<Option<sys_info::MemInfo>, AnyError> {
+) -> Result<Option<sys_info::MemInfo>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("systemMemoryInfo", "Deno.systemMemoryInfo()")?;
@@ -269,7 +300,9 @@ fn op_system_memory_info(
 #[cfg(not(windows))]
 #[op2]
 #[smi]
-fn op_gid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
+fn op_gid(
+  state: &mut OpState,
+) -> Result<Option<u32>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("gid", "Deno.gid()")?;
@@ -283,7 +316,9 @@ fn op_gid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
 #[cfg(windows)]
 #[op2]
 #[smi]
-fn op_gid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
+fn op_gid(
+  state: &mut OpState,
+) -> Result<Option<u32>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("gid", "Deno.gid()")?;
@@ -293,7 +328,9 @@ fn op_gid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
 #[cfg(not(windows))]
 #[op2]
 #[smi]
-fn op_uid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
+fn op_uid(
+  state: &mut OpState,
+) -> Result<Option<u32>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("uid", "Deno.uid()")?;
@@ -307,7 +344,9 @@ fn op_uid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
 #[cfg(windows)]
 #[op2]
 #[smi]
-fn op_uid(state: &mut OpState) -> Result<Option<u32>, AnyError> {
+fn op_uid(
+  state: &mut OpState,
+) -> Result<Option<u32>, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("uid", "Deno.uid()")?;
@@ -485,7 +524,7 @@ fn rss() -> usize {
   }
 }
 
-fn os_uptime(state: &mut OpState) -> Result<u64, AnyError> {
+fn os_uptime(state: &mut OpState) -> Result<u64, deno_core::error::AnyError> {
   state
     .borrow_mut::<PermissionsContainer>()
     .check_sys("osUptime", "Deno.osUptime()")?;
@@ -494,6 +533,8 @@ fn os_uptime(state: &mut OpState) -> Result<u64, AnyError> {
 
 #[op2(fast)]
 #[number]
-fn op_os_uptime(state: &mut OpState) -> Result<u64, AnyError> {
+fn op_os_uptime(
+  state: &mut OpState,
+) -> Result<u64, deno_core::error::AnyError> {
   os_uptime(state)
 }
diff --git a/runtime/ops/process.rs b/runtime/ops/process.rs
index f6555e9324..28913f7c16 100644
--- a/runtime/ops/process.rs
+++ b/runtime/ops/process.rs
@@ -1,8 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::anyhow::Context;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde_json;
 use deno_core::AsyncMutFuture;
@@ -35,6 +32,7 @@ use tokio::process::Command;
 #[cfg(windows)]
 use std::os::windows::process::CommandExt;
 
+use crate::ops::signal::SignalError;
 #[cfg(unix)]
 use std::os::unix::prelude::ExitStatusExt;
 #[cfg(unix)]
@@ -105,11 +103,12 @@ impl StdioOrRid {
   pub fn as_stdio(
     &self,
     state: &mut OpState,
-  ) -> Result<std::process::Stdio, AnyError> {
+  ) -> Result<std::process::Stdio, ProcessError> {
     match &self {
       StdioOrRid::Stdio(val) => Ok(val.as_stdio()),
       StdioOrRid::Rid(rid) => {
         FileResource::with_file(state, *rid, |file| Ok(file.as_stdio()?))
+          .map_err(ProcessError::Resource)
       }
     }
   }
@@ -191,6 +190,39 @@ pub struct SpawnArgs {
   needs_npm_process_state: bool,
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum ProcessError {
+  #[error("Failed to spawn '{command}': {error}")]
+  SpawnFailed {
+    command: String,
+    #[source]
+    error: Box<ProcessError>,
+  },
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[cfg(unix)]
+  #[error(transparent)]
+  Nix(nix::Error),
+  #[error("failed resolving cwd: {0}")]
+  FailedResolvingCwd(#[source] std::io::Error),
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error(transparent)]
+  BorrowMut(std::cell::BorrowMutError),
+  #[error(transparent)]
+  Which(which::Error),
+  #[error("Child process has already terminated.")]
+  ChildProcessAlreadyTerminated,
+  #[error("Invalid pid")]
+  InvalidPid,
+  #[error(transparent)]
+  Signal(#[from] SignalError),
+  #[error("Missing cmd")]
+  MissingCmd, // only for Deno.run
+}
+
 #[derive(Deserialize)]
 #[serde(rename_all = "camelCase")]
 pub struct ChildStdio {
@@ -208,7 +240,7 @@ pub struct ChildStatus {
 }
 
 impl TryFrom<ExitStatus> for ChildStatus {
-  type Error = AnyError;
+  type Error = SignalError;
 
   fn try_from(status: ExitStatus) -> Result<Self, Self::Error> {
     let code = status.code();
@@ -259,7 +291,7 @@ type CreateCommand = (
 
 pub fn npm_process_state_tempfile(
   contents: &[u8],
-) -> Result<deno_io::RawIoHandle, AnyError> {
+) -> Result<deno_io::RawIoHandle, std::io::Error> {
   let mut temp_file = tempfile::tempfile()?;
   temp_file.write_all(contents)?;
   let handle = temp_file.into_raw_io_handle();
@@ -301,7 +333,7 @@ fn create_command(
   state: &mut OpState,
   mut args: SpawnArgs,
   api_name: &str,
-) -> Result<CreateCommand, AnyError> {
+) -> Result<CreateCommand, ProcessError> {
   let maybe_npm_process_state = if args.needs_npm_process_state {
     let provider = state.borrow::<NpmProcessStateProviderRc>();
     let process_state = provider.get_npm_process_state();
@@ -505,7 +537,7 @@ fn spawn_child(
   ipc_pipe_rid: Option<ResourceId>,
   extra_pipe_rids: Vec<Option<ResourceId>>,
   detached: bool,
-) -> Result<Child, AnyError> {
+) -> Result<Child, ProcessError> {
   let mut command = tokio::process::Command::from(command);
   // TODO(@crowlkats): allow detaching processes.
   //  currently deno will orphan a process when exiting with an error or Deno.exit()
@@ -554,10 +586,10 @@ fn spawn_child(
         }
       }
 
-      return Err(AnyError::from(err).context(format!(
-        "Failed to spawn '{}'",
-        command.get_program().to_string_lossy()
-      )));
+      return Err(ProcessError::SpawnFailed {
+        command: command.get_program().to_string_lossy().to_string(),
+        error: Box::new(err.into()),
+      });
     }
   };
 
@@ -600,11 +632,19 @@ fn compute_run_cmd_and_check_permissions(
   arg_clear_env: bool,
   state: &mut OpState,
   api_name: &str,
-) -> Result<(PathBuf, RunEnv), AnyError> {
-  let run_env = compute_run_env(arg_cwd, arg_envs, arg_clear_env)
-    .with_context(|| format!("Failed to spawn '{}'", arg_cmd))?;
-  let cmd = resolve_cmd(arg_cmd, &run_env)
-    .with_context(|| format!("Failed to spawn '{}'", arg_cmd))?;
+) -> Result<(PathBuf, RunEnv), ProcessError> {
+  let run_env =
+    compute_run_env(arg_cwd, arg_envs, arg_clear_env).map_err(|e| {
+      ProcessError::SpawnFailed {
+        command: arg_cmd.to_string(),
+        error: Box::new(e),
+      }
+    })?;
+  let cmd =
+    resolve_cmd(arg_cmd, &run_env).map_err(|e| ProcessError::SpawnFailed {
+      command: arg_cmd.to_string(),
+      error: Box::new(e),
+    })?;
   check_run_permission(
     state,
     &RunQueryDescriptor::Path {
@@ -613,7 +653,8 @@ fn compute_run_cmd_and_check_permissions(
     },
     &run_env,
     api_name,
-  )?;
+  )
+  .map_err(ProcessError::Permission)?;
   Ok((cmd, run_env))
 }
 
@@ -631,9 +672,10 @@ fn compute_run_env(
   arg_cwd: Option<&str>,
   arg_envs: &[(String, String)],
   arg_clear_env: bool,
-) -> Result<RunEnv, AnyError> {
+) -> Result<RunEnv, ProcessError> {
   #[allow(clippy::disallowed_methods)]
-  let cwd = std::env::current_dir().context("failed resolving cwd")?;
+  let cwd =
+    std::env::current_dir().map_err(ProcessError::FailedResolvingCwd)?;
   let cwd = arg_cwd
     .map(|cwd_arg| resolve_path(cwd_arg, &cwd))
     .unwrap_or(cwd);
@@ -670,7 +712,7 @@ fn compute_run_env(
   Ok(RunEnv { envs, cwd })
 }
 
-fn resolve_cmd(cmd: &str, env: &RunEnv) -> Result<PathBuf, AnyError> {
+fn resolve_cmd(cmd: &str, env: &RunEnv) -> Result<PathBuf, ProcessError> {
   let is_path = cmd.contains('/');
   #[cfg(windows)]
   let is_path = is_path || cmd.contains('\\') || Path::new(&cmd).is_absolute();
@@ -683,7 +725,7 @@ fn resolve_cmd(cmd: &str, env: &RunEnv) -> Result<PathBuf, AnyError> {
       Err(which::Error::CannotFindBinaryPath) => {
         Err(std::io::Error::from(std::io::ErrorKind::NotFound).into())
       }
-      Err(err) => Err(err.into()),
+      Err(err) => Err(ProcessError::Which(err)),
     }
   }
 }
@@ -697,7 +739,7 @@ fn check_run_permission(
   cmd: &RunQueryDescriptor,
   run_env: &RunEnv,
   api_name: &str,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let permissions = state.borrow_mut::<PermissionsContainer>();
   if !permissions.query_run_all(api_name) {
     // error the same on all platforms
@@ -754,7 +796,7 @@ fn op_spawn_child(
   state: &mut OpState,
   #[serde] args: SpawnArgs,
   #[string] api_name: String,
-) -> Result<Child, AnyError> {
+) -> Result<Child, ProcessError> {
   let detached = args.detached;
   let (command, pipe_rid, extra_pipe_rids, handles_to_close) =
     create_command(state, args, &api_name)?;
@@ -771,16 +813,23 @@ fn op_spawn_child(
 async fn op_spawn_wait(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<ChildStatus, AnyError> {
+) -> Result<ChildStatus, ProcessError> {
   let resource = state
     .borrow_mut()
     .resource_table
-    .get::<ChildResource>(rid)?;
-  let result = resource.0.try_borrow_mut()?.wait().await?.try_into();
+    .get::<ChildResource>(rid)
+    .map_err(ProcessError::Resource)?;
+  let result = resource
+    .0
+    .try_borrow_mut()
+    .map_err(ProcessError::BorrowMut)?
+    .wait()
+    .await?
+    .try_into()?;
   if let Ok(resource) = state.borrow_mut().resource_table.take_any(rid) {
     resource.close();
   }
-  result
+  Ok(result)
 }
 
 #[op2]
@@ -788,16 +837,14 @@ async fn op_spawn_wait(
 fn op_spawn_sync(
   state: &mut OpState,
   #[serde] args: SpawnArgs,
-) -> Result<SpawnOutput, AnyError> {
+) -> Result<SpawnOutput, ProcessError> {
   let stdout = matches!(args.stdio.stdout, StdioOrRid::Stdio(Stdio::Piped));
   let stderr = matches!(args.stdio.stderr, StdioOrRid::Stdio(Stdio::Piped));
   let (mut command, _, _, _) =
     create_command(state, args, "Deno.Command().outputSync()")?;
-  let output = command.output().with_context(|| {
-    format!(
-      "Failed to spawn '{}'",
-      command.get_program().to_string_lossy()
-    )
+  let output = command.output().map_err(|e| ProcessError::SpawnFailed {
+    command: command.get_program().to_string_lossy().to_string(),
+    error: Box::new(e.into()),
   })?;
 
   Ok(SpawnOutput {
@@ -820,17 +867,15 @@ fn op_spawn_kill(
   state: &mut OpState,
   #[smi] rid: ResourceId,
   #[string] signal: String,
-) -> Result<(), AnyError> {
+) -> Result<(), ProcessError> {
   if let Ok(child_resource) = state.resource_table.get::<ChildResource>(rid) {
     deprecated::kill(child_resource.1 as i32, &signal)?;
     return Ok(());
   }
-  Err(type_error("Child process has already terminated."))
+  Err(ProcessError::ChildProcessAlreadyTerminated)
 }
 
 mod deprecated {
-  use deno_core::anyhow;
-
   use super::*;
 
   #[derive(Deserialize)]
@@ -876,9 +921,9 @@ mod deprecated {
   pub fn op_run(
     state: &mut OpState,
     #[serde] run_args: RunArgs,
-  ) -> Result<RunInfo, AnyError> {
+  ) -> Result<RunInfo, ProcessError> {
     let args = run_args.cmd;
-    let cmd = args.first().ok_or_else(|| anyhow::anyhow!("Missing cmd"))?;
+    let cmd = args.first().ok_or(ProcessError::MissingCmd)?;
     let (cmd, run_env) = compute_run_cmd_and_check_permissions(
       cmd,
       run_args.cwd.as_deref(),
@@ -990,11 +1035,12 @@ mod deprecated {
   pub async fn op_run_status(
     state: Rc<RefCell<OpState>>,
     #[smi] rid: ResourceId,
-  ) -> Result<ProcessStatus, AnyError> {
+  ) -> Result<ProcessStatus, ProcessError> {
     let resource = state
       .borrow_mut()
       .resource_table
-      .get::<ChildResource>(rid)?;
+      .get::<ChildResource>(rid)
+      .map_err(ProcessError::Resource)?;
     let mut child = resource.borrow_mut().await;
     let run_status = child.wait().await?;
     let code = run_status.code();
@@ -1017,17 +1063,17 @@ mod deprecated {
   }
 
   #[cfg(unix)]
-  pub fn kill(pid: i32, signal: &str) -> Result<(), AnyError> {
+  pub fn kill(pid: i32, signal: &str) -> Result<(), ProcessError> {
     let signo = super::super::signal::signal_str_to_int(signal)?;
     use nix::sys::signal::kill as unix_kill;
     use nix::sys::signal::Signal;
     use nix::unistd::Pid;
-    let sig = Signal::try_from(signo)?;
-    unix_kill(Pid::from_raw(pid), Option::Some(sig)).map_err(AnyError::from)
+    let sig = Signal::try_from(signo).map_err(ProcessError::Nix)?;
+    unix_kill(Pid::from_raw(pid), Some(sig)).map_err(ProcessError::Nix)
   }
 
   #[cfg(not(unix))]
-  pub fn kill(pid: i32, signal: &str) -> Result<(), AnyError> {
+  pub fn kill(pid: i32, signal: &str) -> Result<(), ProcessError> {
     use std::io::Error;
     use std::io::ErrorKind::NotFound;
     use winapi::shared::minwindef::DWORD;
@@ -1041,9 +1087,9 @@ mod deprecated {
     use winapi::um::winnt::PROCESS_TERMINATE;
 
     if !matches!(signal, "SIGKILL" | "SIGTERM") {
-      Err(type_error(format!("Invalid signal: {signal}")))
+      Err(SignalError::InvalidSignalStr(signal.to_string()).into())
     } else if pid <= 0 {
-      Err(type_error("Invalid pid"))
+      Err(ProcessError::InvalidPid)
     } else {
       let handle =
         // SAFETY: winapi call
@@ -1077,11 +1123,11 @@ mod deprecated {
     #[smi] pid: i32,
     #[string] signal: String,
     #[string] api_name: String,
-  ) -> Result<(), AnyError> {
+  ) -> Result<(), ProcessError> {
     state
       .borrow_mut::<PermissionsContainer>()
-      .check_run_all(&api_name)?;
-    kill(pid, &signal)?;
-    Ok(())
+      .check_run_all(&api_name)
+      .map_err(ProcessError::Permission)?;
+    kill(pid, &signal)
   }
 }
diff --git a/runtime/ops/runtime.rs b/runtime/ops/runtime.rs
index 419274ebd9..8d54783fc9 100644
--- a/runtime/ops/runtime.rs
+++ b/runtime/ops/runtime.rs
@@ -1,6 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::ModuleSpecifier;
 use deno_core::OpState;
@@ -16,10 +15,9 @@ deno_core::extension!(
 
 #[op2]
 #[string]
-fn op_main_module(state: &mut OpState) -> Result<String, AnyError> {
+fn op_main_module(state: &mut OpState) -> String {
   let main_url = state.borrow::<ModuleSpecifier>();
-  let main_path = main_url.to_string();
-  Ok(main_path)
+  main_url.to_string()
 }
 
 /// This is an op instead of being done at initialization time because
diff --git a/runtime/ops/signal.rs b/runtime/ops/signal.rs
index ebc6db6d1b..e1e4ab68bc 100644
--- a/runtime/ops/signal.rs
+++ b/runtime/ops/signal.rs
@@ -1,6 +1,4 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::AsyncRefCell;
 use deno_core::CancelFuture;
@@ -46,6 +44,42 @@ deno_core::extension!(
   }
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum SignalError {
+  #[cfg(any(
+    target_os = "android",
+    target_os = "linux",
+    target_os = "openbsd",
+    target_os = "openbsd",
+    target_os = "macos",
+    target_os = "solaris",
+    target_os = "illumos"
+  ))]
+  #[error("Invalid signal: {0}")]
+  InvalidSignalStr(String),
+  #[cfg(any(
+    target_os = "android",
+    target_os = "linux",
+    target_os = "openbsd",
+    target_os = "openbsd",
+    target_os = "macos",
+    target_os = "solaris",
+    target_os = "illumos"
+  ))]
+  #[error("Invalid signal: {0}")]
+  InvalidSignalInt(libc::c_int),
+  #[cfg(target_os = "windows")]
+  #[error("Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK), but got {0}")]
+  InvalidSignalStr(String),
+  #[cfg(target_os = "windows")]
+  #[error("Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK), but got {0}")]
+  InvalidSignalInt(libc::c_int),
+  #[error("Binding to signal '{0}' is not allowed")]
+  SignalNotAllowed(String),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+}
+
 #[cfg(unix)]
 #[derive(Default)]
 struct SignalState {
@@ -147,438 +181,217 @@ impl Resource for SignalStreamResource {
   }
 }
 
-#[cfg(target_os = "freebsd")]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGEMT" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGBUS" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGSYS" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGURG" => Ok(16),
-    "SIGSTOP" => Ok(17),
-    "SIGTSTP" => Ok(18),
-    "SIGCONT" => Ok(19),
-    "SIGCHLD" => Ok(20),
-    "SIGTTIN" => Ok(21),
-    "SIGTTOU" => Ok(22),
-    "SIGIO" => Ok(23),
-    "SIGXCPU" => Ok(24),
-    "SIGXFSZ" => Ok(25),
-    "SIGVTALRM" => Ok(26),
-    "SIGPROF" => Ok(27),
-    "SIGWINCH" => Ok(28),
-    "SIGINFO" => Ok(29),
-    "SIGUSR1" => Ok(30),
-    "SIGUSR2" => Ok(31),
-    "SIGTHR" => Ok(32),
-    "SIGLIBRT" => Ok(33),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
+macro_rules! first_literal {
+  ($head:literal $(, $tail:literal)*) => {
+    $head
+  };
+}
+macro_rules! signal_dict {
+  ($(($number:literal, $($name:literal)|+)),*) => {
+    pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, SignalError> {
+      match s {
+        $($($name)|* => Ok($number),)*
+        _ => Err(SignalError::InvalidSignalStr(s.to_string())),
+      }
+    }
+
+    pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, SignalError> {
+      match s {
+        $($number => Ok(first_literal!($($name),+)),)*
+        _ => Err(SignalError::InvalidSignalInt(s)),
+      }
+    }
   }
 }
 
 #[cfg(target_os = "freebsd")]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGEMT"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGBUS"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGSYS"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGURG"),
-    17 => Ok("SIGSTOP"),
-    18 => Ok("SIGTSTP"),
-    19 => Ok("SIGCONT"),
-    20 => Ok("SIGCHLD"),
-    21 => Ok("SIGTTIN"),
-    22 => Ok("SIGTTOU"),
-    23 => Ok("SIGIO"),
-    24 => Ok("SIGXCPU"),
-    25 => Ok("SIGXFSZ"),
-    26 => Ok("SIGVTALRM"),
-    27 => Ok("SIGPROF"),
-    28 => Ok("SIGWINCH"),
-    29 => Ok("SIGINFO"),
-    30 => Ok("SIGUSR1"),
-    31 => Ok("SIGUSR2"),
-    32 => Ok("SIGTHR"),
-    33 => Ok("SIGLIBRT"),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGEMT"),
+  (8, "SIGFPE"),
+  (9, "SIGKILL"),
+  (10, "SIGBUS"),
+  (11, "SIGSEGV"),
+  (12, "SIGSYS"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGURG"),
+  (17, "SIGSTOP"),
+  (18, "SIGTSTP"),
+  (19, "SIGCONT"),
+  (20, "SIGCHLD"),
+  (21, "SIGTTIN"),
+  (22, "SIGTTOU"),
+  (23, "SIGIO"),
+  (24, "SIGXCPU"),
+  (25, "SIGXFSZ"),
+  (26, "SIGVTALRM"),
+  (27, "SIGPROF"),
+  (28, "SIGWINCH"),
+  (29, "SIGINFO"),
+  (30, "SIGUSR1"),
+  (31, "SIGUSR2"),
+  (32, "SIGTHR"),
+  (33, "SIGLIBRT")
+);
 
 #[cfg(target_os = "openbsd")]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGEMT" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGBUS" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGSYS" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGURG" => Ok(16),
-    "SIGSTOP" => Ok(17),
-    "SIGTSTP" => Ok(18),
-    "SIGCONT" => Ok(19),
-    "SIGCHLD" => Ok(20),
-    "SIGTTIN" => Ok(21),
-    "SIGTTOU" => Ok(22),
-    "SIGIO" => Ok(23),
-    "SIGXCPU" => Ok(24),
-    "SIGXFSZ" => Ok(25),
-    "SIGVTALRM" => Ok(26),
-    "SIGPROF" => Ok(27),
-    "SIGWINCH" => Ok(28),
-    "SIGINFO" => Ok(29),
-    "SIGUSR1" => Ok(30),
-    "SIGUSR2" => Ok(31),
-    "SIGTHR" => Ok(32),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
-
-#[cfg(target_os = "openbsd")]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGEMT"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGBUS"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGSYS"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGURG"),
-    17 => Ok("SIGSTOP"),
-    18 => Ok("SIGTSTP"),
-    19 => Ok("SIGCONT"),
-    20 => Ok("SIGCHLD"),
-    21 => Ok("SIGTTIN"),
-    22 => Ok("SIGTTOU"),
-    23 => Ok("SIGIO"),
-    24 => Ok("SIGXCPU"),
-    25 => Ok("SIGXFSZ"),
-    26 => Ok("SIGVTALRM"),
-    27 => Ok("SIGPROF"),
-    28 => Ok("SIGWINCH"),
-    29 => Ok("SIGINFO"),
-    30 => Ok("SIGUSR1"),
-    31 => Ok("SIGUSR2"),
-    32 => Ok("SIGTHR"),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGEMT"),
+  (8, "SIGKILL"),
+  (10, "SIGBUS"),
+  (11, "SIGSEGV"),
+  (12, "SIGSYS"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGURG"),
+  (17, "SIGSTOP"),
+  (18, "SIGTSTP"),
+  (19, "SIGCONT"),
+  (20, "SIGCHLD"),
+  (21, "SIGTTIN"),
+  (22, "SIGTTOU"),
+  (23, "SIGIO"),
+  (24, "SIGXCPU"),
+  (25, "SIGXFSZ"),
+  (26, "SIGVTALRM"),
+  (27, "SIGPROF"),
+  (28, "SIGWINCH"),
+  (29, "SIGINFO"),
+  (30, "SIGUSR1"),
+  (31, "SIGUSR2"),
+  (32, "SIGTHR")
+);
 
 #[cfg(any(target_os = "android", target_os = "linux"))]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGBUS" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGUSR1" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGUSR2" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGSTKFLT" => Ok(16),
-    "SIGCHLD" => Ok(17),
-    "SIGCONT" => Ok(18),
-    "SIGSTOP" => Ok(19),
-    "SIGTSTP" => Ok(20),
-    "SIGTTIN" => Ok(21),
-    "SIGTTOU" => Ok(22),
-    "SIGURG" => Ok(23),
-    "SIGXCPU" => Ok(24),
-    "SIGXFSZ" => Ok(25),
-    "SIGVTALRM" => Ok(26),
-    "SIGPROF" => Ok(27),
-    "SIGWINCH" => Ok(28),
-    "SIGIO" | "SIGPOLL" => Ok(29),
-    "SIGPWR" => Ok(30),
-    "SIGSYS" | "SIGUNUSED" => Ok(31),
-    _ => Err(type_error(format!("Invalid signal : {s}"))),
-  }
-}
-
-#[cfg(any(target_os = "android", target_os = "linux"))]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGBUS"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGUSR1"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGUSR2"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGSTKFLT"),
-    17 => Ok("SIGCHLD"),
-    18 => Ok("SIGCONT"),
-    19 => Ok("SIGSTOP"),
-    20 => Ok("SIGTSTP"),
-    21 => Ok("SIGTTIN"),
-    22 => Ok("SIGTTOU"),
-    23 => Ok("SIGURG"),
-    24 => Ok("SIGXCPU"),
-    25 => Ok("SIGXFSZ"),
-    26 => Ok("SIGVTALRM"),
-    27 => Ok("SIGPROF"),
-    28 => Ok("SIGWINCH"),
-    29 => Ok("SIGIO"),
-    30 => Ok("SIGPWR"),
-    31 => Ok("SIGSYS"),
-    _ => Err(type_error(format!("Invalid signal : {s}"))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGBUS"),
+  (8, "SIGFPE"),
+  (9, "SIGKILL"),
+  (10, "SIGUSR1"),
+  (11, "SIGSEGV"),
+  (12, "SIGUSR2"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGSTKFLT"),
+  (17, "SIGCHLD"),
+  (18, "SIGCONT"),
+  (19, "SIGSTOP"),
+  (20, "SIGTSTP"),
+  (21, "SIGTTIN"),
+  (22, "SIGTTOU"),
+  (23, "SIGURG"),
+  (24, "SIGXCPU"),
+  (25, "SIGXFSZ"),
+  (26, "SIGVTALRM"),
+  (27, "SIGPROF"),
+  (28, "SIGWINCH"),
+  (29, "SIGIO" | "SIGPOLL"),
+  (30, "SIGPWR"),
+  (31, "SIGSYS" | "SIGUNUSED")
+);
 
 #[cfg(target_os = "macos")]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGEMT" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGBUS" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGSYS" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGURG" => Ok(16),
-    "SIGSTOP" => Ok(17),
-    "SIGTSTP" => Ok(18),
-    "SIGCONT" => Ok(19),
-    "SIGCHLD" => Ok(20),
-    "SIGTTIN" => Ok(21),
-    "SIGTTOU" => Ok(22),
-    "SIGIO" => Ok(23),
-    "SIGXCPU" => Ok(24),
-    "SIGXFSZ" => Ok(25),
-    "SIGVTALRM" => Ok(26),
-    "SIGPROF" => Ok(27),
-    "SIGWINCH" => Ok(28),
-    "SIGINFO" => Ok(29),
-    "SIGUSR1" => Ok(30),
-    "SIGUSR2" => Ok(31),
-    _ => Err(type_error(format!("Invalid signal: {s}"))),
-  }
-}
-
-#[cfg(target_os = "macos")]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGEMT"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGBUS"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGSYS"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGURG"),
-    17 => Ok("SIGSTOP"),
-    18 => Ok("SIGTSTP"),
-    19 => Ok("SIGCONT"),
-    20 => Ok("SIGCHLD"),
-    21 => Ok("SIGTTIN"),
-    22 => Ok("SIGTTOU"),
-    23 => Ok("SIGIO"),
-    24 => Ok("SIGXCPU"),
-    25 => Ok("SIGXFSZ"),
-    26 => Ok("SIGVTALRM"),
-    27 => Ok("SIGPROF"),
-    28 => Ok("SIGWINCH"),
-    29 => Ok("SIGINFO"),
-    30 => Ok("SIGUSR1"),
-    31 => Ok("SIGUSR2"),
-    _ => Err(type_error(format!("Invalid signal: {s}"))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGEMT"),
+  (8, "SIGFPE"),
+  (9, "SIGKILL"),
+  (10, "SIGBUS"),
+  (11, "SIGSEGV"),
+  (12, "SIGSYS"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGURG"),
+  (17, "SIGSTOP"),
+  (18, "SIGTSTP"),
+  (19, "SIGCONT"),
+  (20, "SIGCHLD"),
+  (21, "SIGTTIN"),
+  (22, "SIGTTOU"),
+  (23, "SIGIO"),
+  (24, "SIGXCPU"),
+  (25, "SIGXFSZ"),
+  (26, "SIGVTALRM"),
+  (27, "SIGPROF"),
+  (28, "SIGWINCH"),
+  (29, "SIGINFO"),
+  (30, "SIGUSR1"),
+  (31, "SIGUSR2")
+);
 
 #[cfg(any(target_os = "solaris", target_os = "illumos"))]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGHUP" => Ok(1),
-    "SIGINT" => Ok(2),
-    "SIGQUIT" => Ok(3),
-    "SIGILL" => Ok(4),
-    "SIGTRAP" => Ok(5),
-    "SIGIOT" => Ok(6),
-    "SIGABRT" => Ok(6),
-    "SIGEMT" => Ok(7),
-    "SIGFPE" => Ok(8),
-    "SIGKILL" => Ok(9),
-    "SIGBUS" => Ok(10),
-    "SIGSEGV" => Ok(11),
-    "SIGSYS" => Ok(12),
-    "SIGPIPE" => Ok(13),
-    "SIGALRM" => Ok(14),
-    "SIGTERM" => Ok(15),
-    "SIGUSR1" => Ok(16),
-    "SIGUSR2" => Ok(17),
-    "SIGCLD" => Ok(18),
-    "SIGCHLD" => Ok(18),
-    "SIGPWR" => Ok(19),
-    "SIGWINCH" => Ok(20),
-    "SIGURG" => Ok(21),
-    "SIGPOLL" => Ok(22),
-    "SIGIO" => Ok(22),
-    "SIGSTOP" => Ok(23),
-    "SIGTSTP" => Ok(24),
-    "SIGCONT" => Ok(25),
-    "SIGTTIN" => Ok(26),
-    "SIGTTOU" => Ok(27),
-    "SIGVTALRM" => Ok(28),
-    "SIGPROF" => Ok(29),
-    "SIGXCPU" => Ok(30),
-    "SIGXFSZ" => Ok(31),
-    "SIGWAITING" => Ok(32),
-    "SIGLWP" => Ok(33),
-    "SIGFREEZE" => Ok(34),
-    "SIGTHAW" => Ok(35),
-    "SIGCANCEL" => Ok(36),
-    "SIGLOST" => Ok(37),
-    "SIGXRES" => Ok(38),
-    "SIGJVM1" => Ok(39),
-    "SIGJVM2" => Ok(40),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
-
-#[cfg(any(target_os = "solaris", target_os = "illumos"))]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    1 => Ok("SIGHUP"),
-    2 => Ok("SIGINT"),
-    3 => Ok("SIGQUIT"),
-    4 => Ok("SIGILL"),
-    5 => Ok("SIGTRAP"),
-    6 => Ok("SIGABRT"),
-    7 => Ok("SIGEMT"),
-    8 => Ok("SIGFPE"),
-    9 => Ok("SIGKILL"),
-    10 => Ok("SIGBUS"),
-    11 => Ok("SIGSEGV"),
-    12 => Ok("SIGSYS"),
-    13 => Ok("SIGPIPE"),
-    14 => Ok("SIGALRM"),
-    15 => Ok("SIGTERM"),
-    16 => Ok("SIGUSR1"),
-    17 => Ok("SIGUSR2"),
-    18 => Ok("SIGCHLD"),
-    19 => Ok("SIGPWR"),
-    20 => Ok("SIGWINCH"),
-    21 => Ok("SIGURG"),
-    22 => Ok("SIGPOLL"),
-    23 => Ok("SIGSTOP"),
-    24 => Ok("SIGTSTP"),
-    25 => Ok("SIGCONT"),
-    26 => Ok("SIGTTIN"),
-    27 => Ok("SIGTTOU"),
-    28 => Ok("SIGVTALRM"),
-    29 => Ok("SIGPROF"),
-    30 => Ok("SIGXCPU"),
-    31 => Ok("SIGXFSZ"),
-    32 => Ok("SIGWAITING"),
-    33 => Ok("SIGLWP"),
-    34 => Ok("SIGFREEZE"),
-    35 => Ok("SIGTHAW"),
-    36 => Ok("SIGCANCEL"),
-    37 => Ok("SIGLOST"),
-    38 => Ok("SIGXRES"),
-    39 => Ok("SIGJVM1"),
-    40 => Ok("SIGJVM2"),
-    _ => Err(type_error(format!("Invalid signal : {}", s))),
-  }
-}
+signal_dict!(
+  (1, "SIGHUP"),
+  (2, "SIGINT"),
+  (3, "SIGQUIT"),
+  (4, "SIGILL"),
+  (5, "SIGTRAP"),
+  (6, "SIGABRT" | "SIGIOT"),
+  (7, "SIGEMT"),
+  (8, "SIGFPE"),
+  (9, "SIGKILL"),
+  (10, "SIGBUS"),
+  (11, "SIGSEGV"),
+  (12, "SIGSYS"),
+  (13, "SIGPIPE"),
+  (14, "SIGALRM"),
+  (15, "SIGTERM"),
+  (16, "SIGUSR1"),
+  (17, "SIGUSR2"),
+  (18, "SIGCHLD"),
+  (19, "SIGPWR"),
+  (20, "SIGWINCH"),
+  (21, "SIGURG"),
+  (22, "SIGPOLL"),
+  (23, "SIGSTOP"),
+  (24, "SIGTSTP"),
+  (25, "SIGCONT"),
+  (26, "SIGTTIN"),
+  (27, "SIGTTOU"),
+  (28, "SIGVTALRM"),
+  (29, "SIGPROF"),
+  (30, "SIGXCPU"),
+  (31, "SIGXFSZ"),
+  (32, "SIGWAITING"),
+  (33, "SIGLWP"),
+  (34, "SIGFREEZE"),
+  (35, "SIGTHAW"),
+  (36, "SIGCANCEL"),
+  (37, "SIGLOST"),
+  (38, "SIGXRES"),
+  (39, "SIGJVM1"),
+  (40, "SIGJVM2")
+);
 
 #[cfg(target_os = "windows")]
-pub fn signal_str_to_int(s: &str) -> Result<libc::c_int, AnyError> {
-  match s {
-    "SIGINT" => Ok(2),
-    "SIGBREAK" => Ok(21),
-    _ => Err(type_error(
-      "Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK).",
-    )),
-  }
-}
-
-#[cfg(target_os = "windows")]
-pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
-  match s {
-    2 => Ok("SIGINT"),
-    21 => Ok("SIGBREAK"),
-    _ => Err(type_error(
-      "Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK).",
-    )),
-  }
-}
+signal_dict!((2, "SIGINT"), (21, "SIGBREAK"));
 
 #[cfg(unix)]
 #[op2(fast)]
@@ -586,12 +399,10 @@ pub fn signal_int_to_str(s: libc::c_int) -> Result<&'static str, AnyError> {
 fn op_signal_bind(
   state: &mut OpState,
   #[string] sig: &str,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, SignalError> {
   let signo = signal_str_to_int(sig)?;
   if signal_hook_registry::FORBIDDEN.contains(&signo) {
-    return Err(type_error(format!(
-      "Binding to signal '{sig}' is not allowed",
-    )));
+    return Err(SignalError::SignalNotAllowed(sig.to_string()));
   }
 
   let signal = AsyncRefCell::new(signal(SignalKind::from_raw(signo))?);
@@ -625,7 +436,7 @@ fn op_signal_bind(
 fn op_signal_bind(
   state: &mut OpState,
   #[string] sig: &str,
-) -> Result<ResourceId, AnyError> {
+) -> Result<ResourceId, SignalError> {
   let signo = signal_str_to_int(sig)?;
   let resource = SignalStreamResource {
     signal: AsyncRefCell::new(match signo {
@@ -649,7 +460,7 @@ fn op_signal_bind(
 async fn op_signal_poll(
   state: Rc<RefCell<OpState>>,
   #[smi] rid: ResourceId,
-) -> Result<bool, AnyError> {
+) -> Result<bool, deno_core::error::AnyError> {
   let resource = state
     .borrow_mut()
     .resource_table
@@ -668,7 +479,7 @@ async fn op_signal_poll(
 pub fn op_signal_unbind(
   state: &mut OpState,
   #[smi] rid: ResourceId,
-) -> Result<(), AnyError> {
+) -> Result<(), deno_core::error::AnyError> {
   let resource = state.resource_table.take::<SignalStreamResource>(rid)?;
 
   #[cfg(unix)]
diff --git a/runtime/ops/tty.rs b/runtime/ops/tty.rs
index 5b49e3a248..7849185faa 100644
--- a/runtime/ops/tty.rs
+++ b/runtime/ops/tty.rs
@@ -2,7 +2,6 @@
 
 use std::io::Error;
 
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::OpState;
 use rustyline::config::Configurer;
@@ -64,6 +63,19 @@ deno_core::extension!(
   },
 );
 
+#[derive(Debug, thiserror::Error)]
+pub enum TtyError {
+  #[error(transparent)]
+  Resource(deno_core::error::AnyError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[cfg(unix)]
+  #[error(transparent)]
+  Nix(nix::Error),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 // ref: <https://learn.microsoft.com/en-us/windows/console/setconsolemode>
 #[cfg(windows)]
 const COOKED_MODE: DWORD =
@@ -90,8 +102,11 @@ fn op_set_raw(
   rid: u32,
   is_raw: bool,
   cbreak: bool,
-) -> Result<(), AnyError> {
-  let handle_or_fd = state.resource_table.get_fd(rid)?;
+) -> Result<(), TtyError> {
+  let handle_or_fd = state
+    .resource_table
+    .get_fd(rid)
+    .map_err(TtyError::Resource)?;
 
   // From https://github.com/kkawakam/rustyline/blob/master/src/tty/windows.rs
   // and https://github.com/kkawakam/rustyline/blob/master/src/tty/unix.rs
@@ -107,7 +122,7 @@ fn op_set_raw(
     let handle = handle_or_fd;
 
     if cbreak {
-      return Err(deno_core::error::not_supported());
+      return Err(TtyError::Other(deno_core::error::not_supported()));
     }
 
     let mut original_mode: DWORD = 0;
@@ -115,7 +130,7 @@ fn op_set_raw(
     if unsafe { consoleapi::GetConsoleMode(handle, &mut original_mode) }
       == FALSE
     {
-      return Err(Error::last_os_error().into());
+      return Err(TtyError::Io(Error::last_os_error()));
     }
 
     let new_mode = if is_raw {
@@ -185,7 +200,7 @@ fn op_set_raw(
           winapi::um::wincon::WriteConsoleInputW(handle, &record, 1, &mut 0)
         } == FALSE
         {
-          return Err(Error::last_os_error().into());
+          return Err(TtyError::Io(Error::last_os_error()));
         }
 
         /* Wait for read thread to acknowledge the cancellation to ensure that nothing
@@ -199,7 +214,7 @@ fn op_set_raw(
 
     // SAFETY: winapi call
     if unsafe { consoleapi::SetConsoleMode(handle, new_mode) } == FALSE {
-      return Err(Error::last_os_error().into());
+      return Err(TtyError::Io(Error::last_os_error()));
     }
 
     Ok(())
@@ -244,14 +259,16 @@ fn op_set_raw(
     let tty_mode_store = state.borrow::<TtyModeStore>().clone();
     let previous_mode = tty_mode_store.get(rid);
 
-    let raw_fd = handle_or_fd;
+    // SAFETY: Nix crate requires value to implement the AsFd trait
+    let raw_fd = unsafe { std::os::fd::BorrowedFd::borrow_raw(handle_or_fd) };
 
     if is_raw {
       let mut raw = match previous_mode {
         Some(mode) => mode,
         None => {
           // Save original mode.
-          let original_mode = termios::tcgetattr(raw_fd)?;
+          let original_mode =
+            termios::tcgetattr(raw_fd).map_err(TtyError::Nix)?;
           tty_mode_store.set(rid, original_mode.clone());
           original_mode
         }
@@ -273,11 +290,13 @@ fn op_set_raw(
       }
       raw.control_chars[termios::SpecialCharacterIndices::VMIN as usize] = 1;
       raw.control_chars[termios::SpecialCharacterIndices::VTIME as usize] = 0;
-      termios::tcsetattr(raw_fd, termios::SetArg::TCSADRAIN, &raw)?;
+      termios::tcsetattr(raw_fd, termios::SetArg::TCSADRAIN, &raw)
+        .map_err(TtyError::Nix)?;
     } else {
       // Try restore saved mode.
       if let Some(mode) = tty_mode_store.take(rid) {
-        termios::tcsetattr(raw_fd, termios::SetArg::TCSADRAIN, &mode)?;
+        termios::tcsetattr(raw_fd, termios::SetArg::TCSADRAIN, &mode)
+          .map_err(TtyError::Nix)?;
       }
     }
 
@@ -289,13 +308,16 @@ fn op_set_raw(
 fn op_console_size(
   state: &mut OpState,
   #[buffer] result: &mut [u32],
-) -> Result<(), AnyError> {
+) -> Result<(), TtyError> {
   fn check_console_size(
     state: &mut OpState,
     result: &mut [u32],
     rid: u32,
-  ) -> Result<(), AnyError> {
-    let fd = state.resource_table.get_fd(rid)?;
+  ) -> Result<(), TtyError> {
+    let fd = state
+      .resource_table
+      .get_fd(rid)
+      .map_err(TtyError::Resource)?;
     let size = console_size_from_fd(fd)?;
     result[0] = size.cols;
     result[1] = size.rows;
@@ -418,7 +440,7 @@ mod tests {
 pub fn op_read_line_prompt(
   #[string] prompt_text: &str,
   #[string] default_value: &str,
-) -> Result<Option<String>, AnyError> {
+) -> Result<Option<String>, ReadlineError> {
   let mut editor = Editor::<(), rustyline::history::DefaultHistory>::new()
     .expect("Failed to create editor.");
 
@@ -438,6 +460,6 @@ pub fn op_read_line_prompt(
       Ok(None)
     }
     Err(ReadlineError::Eof) => Ok(None),
-    Err(err) => Err(err.into()),
+    Err(err) => Err(err),
   }
 }
diff --git a/runtime/ops/utils.rs b/runtime/ops/utils.rs
deleted file mode 100644
index d5ce61c1fa..0000000000
--- a/runtime/ops/utils.rs
+++ /dev/null
@@ -1,12 +0,0 @@
-// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-
-use deno_core::error::custom_error;
-use deno_core::error::AnyError;
-
-/// A utility function to map OsStrings to Strings
-pub fn into_string(s: std::ffi::OsString) -> Result<String, AnyError> {
-  s.into_string().map_err(|s| {
-    let message = format!("File name or path {s:?} is not valid UTF-8");
-    custom_error("InvalidData", message)
-  })
-}
diff --git a/runtime/ops/web_worker.rs b/runtime/ops/web_worker.rs
index 0ed76ebd50..d0c3eea668 100644
--- a/runtime/ops/web_worker.rs
+++ b/runtime/ops/web_worker.rs
@@ -4,15 +4,16 @@ mod sync_fetch;
 
 use crate::web_worker::WebWorkerInternalHandle;
 use crate::web_worker::WebWorkerType;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::CancelFuture;
 use deno_core::OpState;
 use deno_web::JsMessageData;
+use deno_web::MessagePortError;
 use std::cell::RefCell;
 use std::rc::Rc;
 
 use self::sync_fetch::op_worker_sync_fetch;
+pub use sync_fetch::SyncFetchError;
 
 deno_core::extension!(
   deno_web_worker,
@@ -30,17 +31,16 @@ deno_core::extension!(
 fn op_worker_post_message(
   state: &mut OpState,
   #[serde] data: JsMessageData,
-) -> Result<(), AnyError> {
+) -> Result<(), MessagePortError> {
   let handle = state.borrow::<WebWorkerInternalHandle>().clone();
-  handle.port.send(state, data)?;
-  Ok(())
+  handle.port.send(state, data)
 }
 
 #[op2(async(lazy), fast)]
 #[serde]
 async fn op_worker_recv_message(
   state: Rc<RefCell<OpState>>,
-) -> Result<Option<JsMessageData>, AnyError> {
+) -> Result<Option<JsMessageData>, MessagePortError> {
   let handle = {
     let state = state.borrow();
     state.borrow::<WebWorkerInternalHandle>().clone()
diff --git a/runtime/ops/web_worker/sync_fetch.rs b/runtime/ops/web_worker/sync_fetch.rs
index cdb151a86f..d1f133d3d2 100644
--- a/runtime/ops/web_worker/sync_fetch.rs
+++ b/runtime/ops/web_worker/sync_fetch.rs
@@ -4,15 +4,13 @@ use std::sync::Arc;
 
 use crate::web_worker::WebWorkerInternalHandle;
 use crate::web_worker::WebWorkerType;
-use deno_core::error::type_error;
-use deno_core::error::AnyError;
 use deno_core::futures::StreamExt;
 use deno_core::op2;
 use deno_core::url::Url;
 use deno_core::OpState;
 use deno_fetch::data_url::DataUrl;
+use deno_fetch::FetchError;
 use deno_web::BlobStore;
-use deno_websocket::DomExceptionNetworkError;
 use http_body_util::BodyExt;
 use hyper::body::Bytes;
 use serde::Deserialize;
@@ -27,6 +25,32 @@ fn mime_type_essence(mime_type: &str) -> String {
   essence.trim().to_ascii_lowercase()
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum SyncFetchError {
+  #[error("Blob URLs are not supported in this context.")]
+  BlobUrlsNotSupportedInContext,
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+  #[error("Invalid script URL")]
+  InvalidScriptUrl,
+  #[error("http status error: {0}")]
+  InvalidStatusCode(http::StatusCode),
+  #[error("Classic scripts with scheme {0}: are not supported in workers")]
+  ClassicScriptSchemeUnsupportedInWorkers(String),
+  #[error("{0}")]
+  InvalidUri(#[from] http::uri::InvalidUri),
+  #[error("Invalid MIME type {0:?}.")]
+  InvalidMimeType(String),
+  #[error("Missing MIME type.")]
+  MissingMimeType,
+  #[error(transparent)]
+  Fetch(#[from] FetchError),
+  #[error(transparent)]
+  Join(#[from] tokio::task::JoinError),
+  #[error(transparent)]
+  Other(deno_core::error::AnyError),
+}
+
 #[derive(Serialize, Deserialize)]
 #[serde(rename_all = "camelCase")]
 pub struct SyncFetchScript {
@@ -40,21 +64,22 @@ pub fn op_worker_sync_fetch(
   state: &mut OpState,
   #[serde] scripts: Vec<String>,
   loose_mime_checks: bool,
-) -> Result<Vec<SyncFetchScript>, AnyError> {
+) -> Result<Vec<SyncFetchScript>, SyncFetchError> {
   let handle = state.borrow::<WebWorkerInternalHandle>().clone();
   assert_eq!(handle.worker_type, WebWorkerType::Classic);
 
   // it's not safe to share a client across tokio runtimes, so create a fresh one
   // https://github.com/seanmonstar/reqwest/issues/1148#issuecomment-910868788
   let options = state.borrow::<deno_fetch::Options>().clone();
-  let client = deno_fetch::create_client_from_options(&options)?;
+  let client = deno_fetch::create_client_from_options(&options)
+    .map_err(FetchError::ClientCreate)?;
 
   // TODO(andreubotella) It's not good to throw an exception related to blob
   // URLs when none of the script URLs use the blob scheme.
   // Also, in which contexts are blob URLs not supported?
   let blob_store = state
     .try_borrow::<Arc<BlobStore>>()
-    .ok_or_else(|| type_error("Blob URLs are not supported in this context."))?
+    .ok_or(SyncFetchError::BlobUrlsNotSupportedInContext)?
     .clone();
 
   // TODO(andreubotella): make the below thread into a resource that can be
@@ -74,7 +99,7 @@ pub fn op_worker_sync_fetch(
           let blob_store = blob_store.clone();
           deno_core::unsync::spawn(async move {
             let script_url = Url::parse(&script)
-              .map_err(|_| type_error("Invalid script URL"))?;
+              .map_err(|_| SyncFetchError::InvalidScriptUrl)?;
             let mut loose_mime_checks = loose_mime_checks;
 
             let (body, mime_type, res_url) = match script_url.scheme() {
@@ -86,15 +111,13 @@ pub fn op_worker_sync_fetch(
                 );
                 *req.uri_mut() = script_url.as_str().parse()?;
 
-                let resp = client.send(req).await?;
+                let resp =
+                  client.send(req).await.map_err(FetchError::ClientSend)?;
 
                 if resp.status().is_client_error()
                   || resp.status().is_server_error()
                 {
-                  return Err(type_error(format!(
-                    "http status error: {}",
-                    resp.status()
-                  )));
+                  return Err(SyncFetchError::InvalidStatusCode(resp.status()));
                 }
 
                 // TODO(andreubotella) Properly run fetch's "extract a MIME type".
@@ -107,42 +130,45 @@ pub fn op_worker_sync_fetch(
                 // Always check the MIME type with HTTP(S).
                 loose_mime_checks = false;
 
-                let body = resp.collect().await?.to_bytes();
+                let body = resp
+                  .collect()
+                  .await
+                  .map_err(SyncFetchError::Other)?
+                  .to_bytes();
 
                 (body, mime_type, script)
               }
               "data" => {
-                let data_url = DataUrl::process(&script)
-                  .map_err(|e| type_error(format!("{e:?}")))?;
+                let data_url =
+                  DataUrl::process(&script).map_err(FetchError::DataUrl)?;
 
                 let mime_type = {
                   let mime = data_url.mime_type();
                   format!("{}/{}", mime.type_, mime.subtype)
                 };
 
-                let (body, _) = data_url
-                  .decode_to_vec()
-                  .map_err(|e| type_error(format!("{e:?}")))?;
+                let (body, _) =
+                  data_url.decode_to_vec().map_err(FetchError::Base64)?;
 
                 (Bytes::from(body), Some(mime_type), script)
               }
               "blob" => {
-                let blob =
-                  blob_store.get_object_url(script_url).ok_or_else(|| {
-                    type_error("Blob for the given URL not found.")
-                  })?;
+                let blob = blob_store
+                  .get_object_url(script_url)
+                  .ok_or(FetchError::BlobNotFound)?;
 
                 let mime_type = mime_type_essence(&blob.media_type);
 
-                let body = blob.read_all().await?;
+                let body = blob.read_all().await;
 
                 (Bytes::from(body), Some(mime_type), script)
               }
               _ => {
-                return Err(type_error(format!(
-              "Classic scripts with scheme {}: are not supported in workers.",
-              script_url.scheme()
-            )))
+                return Err(
+                  SyncFetchError::ClassicScriptSchemeUnsupportedInWorkers(
+                    script_url.scheme().to_string(),
+                  ),
+                )
               }
             };
 
@@ -151,18 +177,11 @@ pub fn op_worker_sync_fetch(
               match mime_type.as_deref() {
                 Some("application/javascript" | "text/javascript") => {}
                 Some(mime_type) => {
-                  return Err(
-                    DomExceptionNetworkError {
-                      msg: format!("Invalid MIME type {mime_type:?}."),
-                    }
-                    .into(),
-                  )
-                }
-                None => {
-                  return Err(
-                    DomExceptionNetworkError::new("Missing MIME type.").into(),
-                  )
+                  return Err(SyncFetchError::InvalidMimeType(
+                    mime_type.to_string(),
+                  ))
                 }
+                None => return Err(SyncFetchError::MissingMimeType),
               }
             }
 
diff --git a/runtime/ops/worker_host.rs b/runtime/ops/worker_host.rs
index b9fd066543..82cc949242 100644
--- a/runtime/ops/worker_host.rs
+++ b/runtime/ops/worker_host.rs
@@ -10,7 +10,6 @@ use crate::web_worker::WorkerControlEvent;
 use crate::web_worker::WorkerId;
 use crate::web_worker::WorkerMetadata;
 use crate::worker::FormatJsErrorFn;
-use deno_core::error::AnyError;
 use deno_core::op2;
 use deno_core::serde::Deserialize;
 use deno_core::CancelFuture;
@@ -21,6 +20,7 @@ use deno_permissions::ChildPermissionsArg;
 use deno_permissions::PermissionsContainer;
 use deno_web::deserialize_js_transferables;
 use deno_web::JsMessageData;
+use deno_web::MessagePortError;
 use log::debug;
 use std::cell::RefCell;
 use std::collections::HashMap;
@@ -118,6 +118,20 @@ pub struct CreateWorkerArgs {
   close_on_idle: bool,
 }
 
+#[derive(Debug, thiserror::Error)]
+pub enum CreateWorkerError {
+  #[error("Classic workers are not supported.")]
+  ClassicWorkers,
+  #[error(transparent)]
+  Permission(deno_core::error::AnyError),
+  #[error(transparent)]
+  ModuleResolution(#[from] deno_core::ModuleResolutionError),
+  #[error(transparent)]
+  MessagePort(#[from] MessagePortError),
+  #[error("{0}")]
+  Io(#[from] std::io::Error),
+}
+
 /// Create worker as the host
 #[op2]
 #[serde]
@@ -125,7 +139,7 @@ fn op_create_worker(
   state: &mut OpState,
   #[serde] args: CreateWorkerArgs,
   #[serde] maybe_worker_metadata: Option<JsMessageData>,
-) -> Result<WorkerId, AnyError> {
+) -> Result<WorkerId, CreateWorkerError> {
   let specifier = args.specifier.clone();
   let maybe_source_code = if args.has_source_code {
     Some(args.source_code.clone())
@@ -136,12 +150,7 @@ fn op_create_worker(
   let worker_type = args.worker_type;
   if let WebWorkerType::Classic = worker_type {
     if let TestingFeaturesEnabled(false) = state.borrow() {
-      return Err(
-        deno_webstorage::DomExceptionNotSupportedError::new(
-          "Classic workers are not supported.",
-        )
-        .into(),
-      );
+      return Err(CreateWorkerError::ClassicWorkers);
     }
   }
 
@@ -155,7 +164,9 @@ fn op_create_worker(
   let parent_permissions = state.borrow_mut::<PermissionsContainer>();
   let worker_permissions = if let Some(child_permissions_arg) = args.permissions
   {
-    parent_permissions.create_child_permissions(child_permissions_arg)?
+    parent_permissions
+      .create_child_permissions(child_permissions_arg)
+      .map_err(CreateWorkerError::Permission)?
   } else {
     parent_permissions.clone()
   };
@@ -167,9 +178,8 @@ fn op_create_worker(
   let module_specifier = deno_core::resolve_url(&specifier)?;
   let worker_name = args_name.unwrap_or_default();
 
-  let (handle_sender, handle_receiver) = std::sync::mpsc::sync_channel::<
-    Result<SendableWebWorkerHandle, AnyError>,
-  >(1);
+  let (handle_sender, handle_receiver) =
+    std::sync::mpsc::sync_channel::<SendableWebWorkerHandle>(1);
 
   // Setup new thread
   let thread_builder = std::thread::Builder::new().name(format!("{worker_id}"));
@@ -203,7 +213,7 @@ fn op_create_worker(
       });
 
     // Send thread safe handle from newly created worker to host thread
-    handle_sender.send(Ok(external_handle)).unwrap();
+    handle_sender.send(external_handle).unwrap();
     drop(handle_sender);
 
     // At this point the only method of communication with host
@@ -219,7 +229,7 @@ fn op_create_worker(
   })?;
 
   // Receive WebWorkerHandle from newly created worker
-  let worker_handle = handle_receiver.recv().unwrap()?;
+  let worker_handle = handle_receiver.recv().unwrap();
 
   let worker_thread = WorkerThread {
     worker_handle: worker_handle.into(),
@@ -292,7 +302,7 @@ fn close_channel(
 async fn op_host_recv_ctrl(
   state: Rc<RefCell<OpState>>,
   #[serde] id: WorkerId,
-) -> Result<WorkerControlEvent, AnyError> {
+) -> WorkerControlEvent {
   let (worker_handle, cancel_handle) = {
     let state = state.borrow();
     let workers_table = state.borrow::<WorkersTable>();
@@ -301,7 +311,7 @@ async fn op_host_recv_ctrl(
       (handle.worker_handle.clone(), handle.cancel_handle.clone())
     } else {
       // If handle was not found it means worker has already shutdown
-      return Ok(WorkerControlEvent::Close);
+      return WorkerControlEvent::Close;
     }
   };
 
@@ -310,22 +320,21 @@ async fn op_host_recv_ctrl(
     .or_cancel(cancel_handle)
     .await;
   match maybe_event {
-    Ok(Ok(Some(event))) => {
+    Ok(Some(event)) => {
       // Terminal error means that worker should be removed from worker table.
       if let WorkerControlEvent::TerminalError(_) = &event {
         close_channel(state, id, WorkerChannel::Ctrl);
       }
-      Ok(event)
+      event
     }
-    Ok(Ok(None)) => {
+    Ok(None) => {
       // If there was no event from worker it means it has already been closed.
       close_channel(state, id, WorkerChannel::Ctrl);
-      Ok(WorkerControlEvent::Close)
+      WorkerControlEvent::Close
     }
-    Ok(Err(err)) => Err(err),
     Err(_) => {
       // The worker was terminated.
-      Ok(WorkerControlEvent::Close)
+      WorkerControlEvent::Close
     }
   }
 }
@@ -335,7 +344,7 @@ async fn op_host_recv_ctrl(
 async fn op_host_recv_message(
   state: Rc<RefCell<OpState>>,
   #[serde] id: WorkerId,
-) -> Result<Option<JsMessageData>, AnyError> {
+) -> Result<Option<JsMessageData>, MessagePortError> {
   let (worker_handle, cancel_handle) = {
     let s = state.borrow();
     let workers_table = s.borrow::<WorkersTable>();
@@ -374,7 +383,7 @@ fn op_host_post_message(
   state: &mut OpState,
   #[serde] id: WorkerId,
   #[serde] data: JsMessageData,
-) -> Result<(), AnyError> {
+) -> Result<(), MessagePortError> {
   if let Some(worker_thread) = state.borrow::<WorkersTable>().get(&id) {
     debug!("post message to worker {}", id);
     let worker_handle = worker_thread.worker_handle.clone();
diff --git a/runtime/permissions/Cargo.toml b/runtime/permissions/Cargo.toml
index 8f0b0dd3de..bfa37b4898 100644
--- a/runtime/permissions/Cargo.toml
+++ b/runtime/permissions/Cargo.toml
@@ -2,7 +2,7 @@
 
 [package]
 name = "deno_permissions"
-version = "0.31.0"
+version = "0.35.0"
 authors.workspace = true
 edition.workspace = true
 license.workspace = true
diff --git a/runtime/permissions/lib.rs b/runtime/permissions/lib.rs
index 2904242dae..84503f025b 100644
--- a/runtime/permissions/lib.rs
+++ b/runtime/permissions/lib.rs
@@ -35,11 +35,13 @@ use std::sync::Arc;
 
 pub mod prompter;
 use prompter::permission_prompt;
-use prompter::PromptResponse;
 use prompter::PERMISSION_EMOJI;
 
 pub use prompter::set_prompt_callbacks;
+pub use prompter::set_prompter;
+pub use prompter::PermissionPrompter;
 pub use prompter::PromptCallback;
+pub use prompter::PromptResponse;
 
 /// Fast exit from permission check routines if this permission
 /// is in the "fully-granted" state.
@@ -1366,8 +1368,12 @@ impl SysDescriptor {
     match kind.as_str() {
       "hostname" | "osRelease" | "osUptime" | "loadavg"
       | "networkInterfaces" | "systemMemoryInfo" | "uid" | "gid" | "cpus"
-      | "homedir" | "getegid" | "username" | "statfs" | "getPriority"
-      | "setPriority" => Ok(Self(kind)),
+      | "homedir" | "getegid" | "statfs" | "getPriority" | "setPriority"
+      | "userInfo" => Ok(Self(kind)),
+
+      // the underlying permission check changed to `userInfo` to better match the API,
+      // alias this to avoid breaking existing projects with `--allow-sys=username`
+      "username" => Ok(Self("userInfo".into())),
       _ => Err(type_error(format!("unknown system info kind \"{kind}\""))),
     }
   }
diff --git a/runtime/permissions/prompter.rs b/runtime/permissions/prompter.rs
index e48e0af10d..b582b4f53e 100644
--- a/runtime/permissions/prompter.rs
+++ b/runtime/permissions/prompter.rs
@@ -80,6 +80,10 @@ pub fn set_prompt_callbacks(
   *MAYBE_AFTER_PROMPT_CALLBACK.lock() = Some(after_callback);
 }
 
+pub fn set_prompter(prompter: Box<dyn PermissionPrompter>) {
+  *PERMISSION_PROMPTER.lock() = prompter;
+}
+
 pub type PromptCallback = Box<dyn FnMut() + Send + Sync>;
 
 pub trait PermissionPrompter: Send + Sync {
@@ -265,7 +269,7 @@ fn get_stdin_metadata() -> std::io::Result<std::fs::Metadata> {
   unsafe {
     let stdin = std::fs::File::from_raw_fd(0);
     let metadata = stdin.metadata().unwrap();
-    stdin.into_raw_fd();
+    let _ = stdin.into_raw_fd();
     Ok(metadata)
   }
 }
@@ -366,7 +370,7 @@ impl PermissionPrompter for TtyPrompter {
 
       let mut input = String::new();
       let result = stdin_lock.read_line(&mut input);
-      let input = input.trim_end_matches(|c| c == '\r' || c == '\n');
+      let input = input.trim_end_matches(['\r', '\n']);
       if result.is_err() || input.len() != 1 {
         break PromptResponse::Deny;
       };
@@ -476,8 +480,4 @@ pub mod tests {
       STUB_PROMPT_VALUE.store(value, Ordering::SeqCst);
     }
   }
-
-  pub fn set_prompter(prompter: Box<dyn PermissionPrompter>) {
-    *PERMISSION_PROMPTER.lock() = prompter;
-  }
 }
diff --git a/runtime/shared.rs b/runtime/shared.rs
index 02dfd18719..f7d76f67a7 100644
--- a/runtime/shared.rs
+++ b/runtime/shared.rs
@@ -98,6 +98,7 @@ pub fn maybe_transpile_source(
         imports_not_used_as_values: deno_ast::ImportsNotUsedAsValues::Remove,
         ..Default::default()
       },
+      &deno_ast::TranspileModuleOptions::default(),
       &deno_ast::EmitOptions {
         source_map: if cfg!(debug_assertions) {
           SourceMapOption::Separate
@@ -109,9 +110,9 @@ pub fn maybe_transpile_source(
     )?
     .into_source();
 
-  let maybe_source_map: Option<SourceMapData> =
-    transpiled_source.source_map.map(|sm| sm.into());
-  let source_text = String::from_utf8(transpiled_source.source)?;
-
+  let maybe_source_map: Option<SourceMapData> = transpiled_source
+    .source_map
+    .map(|sm| sm.into_bytes().into());
+  let source_text = transpiled_source.text;
   Ok((source_text.into(), maybe_source_map))
 }
diff --git a/runtime/tokio_util.rs b/runtime/tokio_util.rs
index 0d81f6e235..aa0282ece8 100644
--- a/runtime/tokio_util.rs
+++ b/runtime/tokio_util.rs
@@ -43,7 +43,15 @@ pub fn create_basic_runtime() -> tokio::runtime::Runtime {
     // parallel for deno fmt.
     // The default value is 512, which is an unhelpfully large thread pool. We
     // don't ever want to have more than a couple dozen threads.
-    .max_blocking_threads(32)
+    .max_blocking_threads(if cfg!(windows) {
+      // on windows, tokio uses blocking tasks for child process IO, make sure
+      // we have enough available threads for other tasks to run
+      4 * std::thread::available_parallelism()
+        .map(|n| n.get())
+        .unwrap_or(8)
+    } else {
+      32
+    })
     .build()
     .unwrap()
 }
diff --git a/runtime/web_worker.rs b/runtime/web_worker.rs
index f560ce17ec..04cd3305e5 100644
--- a/runtime/web_worker.rs
+++ b/runtime/web_worker.rs
@@ -166,7 +166,10 @@ pub struct WebWorkerInternalHandle {
 
 impl WebWorkerInternalHandle {
   /// Post WorkerEvent to parent as a worker
-  pub fn post_event(&self, event: WorkerControlEvent) -> Result<(), AnyError> {
+  pub fn post_event(
+    &self,
+    event: WorkerControlEvent,
+  ) -> Result<(), mpsc::TrySendError<WorkerControlEvent>> {
     let mut sender = self.sender.clone();
     // If the channel is closed,
     // the worker must have terminated but the termination message has not yet been received.
@@ -176,8 +179,7 @@ impl WebWorkerInternalHandle {
       self.has_terminated.store(true, Ordering::SeqCst);
       return Ok(());
     }
-    sender.try_send(event)?;
-    Ok(())
+    sender.try_send(event)
   }
 
   /// Check if this worker is terminated or being terminated
@@ -263,11 +265,9 @@ impl WebWorkerHandle {
   /// Get the WorkerEvent with lock
   /// Return error if more than one listener tries to get event
   #[allow(clippy::await_holding_refcell_ref)] // TODO(ry) remove!
-  pub async fn get_control_event(
-    &self,
-  ) -> Result<Option<WorkerControlEvent>, AnyError> {
+  pub async fn get_control_event(&self) -> Option<WorkerControlEvent> {
     let mut receiver = self.receiver.borrow_mut();
-    Ok(receiver.next().await)
+    receiver.next().await
   }
 
   /// Terminate the worker
diff --git a/runtime/worker.rs b/runtime/worker.rs
index 477d3b880c..b780aefc1b 100644
--- a/runtime/worker.rs
+++ b/runtime/worker.rs
@@ -20,6 +20,8 @@ use deno_core::CompiledWasmModuleStore;
 use deno_core::Extension;
 use deno_core::FeatureChecker;
 use deno_core::GetErrorClassFn;
+use deno_core::InspectorSessionKind;
+use deno_core::InspectorSessionOptions;
 use deno_core::JsRuntime;
 use deno_core::LocalInspectorSession;
 use deno_core::ModuleCodeString;
@@ -792,7 +794,11 @@ impl MainWorker {
   /// was not configured to create inspector.
   pub fn create_inspector_session(&mut self) -> LocalInspectorSession {
     self.js_runtime.maybe_init_inspector();
-    self.js_runtime.inspector().borrow().create_local_session()
+    self.js_runtime.inspector().borrow().create_local_session(
+      InspectorSessionOptions {
+        kind: InspectorSessionKind::Blocking,
+      },
+    )
   }
 
   pub async fn run_event_loop(
diff --git a/rust-toolchain.toml b/rust-toolchain.toml
index e8d3cddd18..3d572e0d69 100644
--- a/rust-toolchain.toml
+++ b/rust-toolchain.toml
@@ -1,3 +1,3 @@
 [toolchain]
-channel = "1.80.1"
+channel = "1.82.0"
 components = ["rustfmt", "clippy"]
diff --git a/tests/ffi/tests/integration_tests.rs b/tests/ffi/tests/integration_tests.rs
index c84a1b820d..dbc0036bc2 100644
--- a/tests/ffi/tests/integration_tests.rs
+++ b/tests/ffi/tests/integration_tests.rs
@@ -95,10 +95,10 @@ fn basic() {
     579.912\n\
     579.912\n\
     579\n\
-    8589934590\n\
-    -8589934590\n\
-    8589934590\n\
-    -8589934590\n\
+    8589934590n\n\
+    -8589934590n\n\
+    8589934590n\n\
+    -8589934590n\n\
     9007199254740992n\n\
     9007199254740992n\n\
     -9007199254740992n\n\
diff --git a/tests/integration/compile_tests.rs b/tests/integration/compile_tests.rs
index 0a5916f6f7..fa6364a136 100644
--- a/tests/integration/compile_tests.rs
+++ b/tests/integration/compile_tests.rs
@@ -241,7 +241,7 @@ fn compile_with_file_exists_error() {
       "./compile/args.ts",
     ])
     .run()
-    .assert_matches_text(&format!(
+    .assert_matches_text(format!(
       concat!(
         "[WILDCARD]error: Could not compile to file '{}' because its parent directory ",
         "is an existing file. You can use the `--output <file-path>` flag to ",
@@ -269,7 +269,7 @@ fn compile_with_directory_exists_error() {
       &exe.to_string_lossy(),
       "./compile/args.ts"
     ]).run()
-    .assert_matches_text(&format!(
+    .assert_matches_text(format!(
       concat!(
         "[WILDCARD]error: Could not compile to file '{}' because a directory exists with ",
         "the same name. You can use the `--output <file-path>` flag to ",
@@ -297,7 +297,7 @@ fn compile_with_conflict_file_exists_error() {
       &exe.to_string_lossy(),
       "./compile/args.ts"
     ]).run()
-    .assert_matches_text(&format!(
+    .assert_matches_text(format!(
       concat!(
         "[WILDCARD]error: Could not compile to file '{}' because the file already exists ",
         "and cannot be overwritten. Please delete the existing file or ",
@@ -1111,7 +1111,7 @@ console.log(getValue());"#,
     .run();
   output.assert_exit_code(0);
   output.assert_matches_text(
-    r#"Download http://localhost:4260/@denotest/esm-basic
+    r#"Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file:///[WILDCARD]/main.ts
diff --git a/tests/integration/flags_tests.rs b/tests/integration/flags_tests.rs
index 455507b9fa..663da363da 100644
--- a/tests/integration/flags_tests.rs
+++ b/tests/integration/flags_tests.rs
@@ -18,8 +18,8 @@ fn help_output() {
     "Start an interactive Read-Eval-Print Loop (REPL) for Deno",
     "Evaluate a script from the command line",
     "Add dependencies",
-    "Install script as an executable",
-    "Uninstall a script previously installed with deno install",
+    "Installs dependencies either in the local project or globally to a bin directory",
+    "Uninstalls a dependency or an executable script in the installation root's bin directory",
     "Run benchmarks",
     "Type-check the dependencies",
     "Compile the script into a self contained executable",
diff --git a/tests/integration/lsp_tests.rs b/tests/integration/lsp_tests.rs
index 19ea89a54b..2376aebd90 100644
--- a/tests/integration/lsp_tests.rs
+++ b/tests/integration/lsp_tests.rs
@@ -1049,6 +1049,191 @@ fn lsp_workspace_enable_paths_no_workspace_configuration() {
   client.shutdown();
 }
 
+#[test]
+fn lsp_did_refresh_deno_configuration_tree_notification() {
+  let context = TestContextBuilder::new().use_temp_cwd().build();
+  let temp_dir = context.temp_dir();
+  temp_dir.create_dir_all("workspace/member1");
+  temp_dir.create_dir_all("workspace/member2");
+  temp_dir.create_dir_all("non_workspace1");
+  temp_dir.create_dir_all("non_workspace2");
+  temp_dir.write(
+    "workspace/deno.json",
+    json!({
+      "workspace": [
+        "member1",
+        "member2",
+      ],
+    })
+    .to_string(),
+  );
+  temp_dir.write("workspace/member1/deno.json", json!({}).to_string());
+  temp_dir.write("workspace/member1/package.json", json!({}).to_string());
+  temp_dir.write("workspace/member2/package.json", json!({}).to_string());
+  temp_dir.write("non_workspace1/deno.json", json!({}).to_string());
+  let mut client = context.new_lsp_command().build();
+  client.initialize_default();
+  let res = client
+    .read_notification_with_method::<Value>(
+      "deno/didRefreshDenoConfigurationTree",
+    )
+    .unwrap();
+  assert_eq!(
+    res,
+    json!({
+      "data": [
+        {
+          "scopeUri": temp_dir.url().join("non_workspace1/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("non_workspace1/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member1/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/member1/deno.json").unwrap(),
+          },
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member1/package.json").unwrap(),
+          },
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member2/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": null,
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member2/package.json").unwrap(),
+          },
+        },
+      ],
+    }),
+  );
+  temp_dir.write("non_workspace2/deno.json", json!({}).to_string());
+  client.did_change_watched_files(json!({
+    "changes": [{
+      "uri": temp_dir.url().join("non_workspace2/deno.json").unwrap(),
+      "type": 1,
+    }],
+  }));
+  let res = client
+    .read_notification_with_method::<Value>(
+      "deno/didRefreshDenoConfigurationTree",
+    )
+    .unwrap();
+  assert_eq!(
+    res,
+    json!({
+      "data": [
+        {
+          "scopeUri": temp_dir.url().join("non_workspace1/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("non_workspace1/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("non_workspace2/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("non_workspace2/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member1/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/member1/deno.json").unwrap(),
+          },
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member1/package.json").unwrap(),
+          },
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member2/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": null,
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member2/package.json").unwrap(),
+          },
+        },
+      ],
+    }),
+  );
+  client.change_configuration(json!({
+    "deno": {
+      "disablePaths": ["non_workspace1"],
+    },
+  }));
+  let res = client
+    .read_notification_with_method::<Value>(
+      "deno/didRefreshDenoConfigurationTree",
+    )
+    .unwrap();
+  assert_eq!(
+    res,
+    json!({
+      "data": [
+        {
+          "scopeUri": temp_dir.url().join("non_workspace2/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("non_workspace2/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "workspaceRootScopeUri": null,
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/deno.json").unwrap(),
+          },
+          "packageJson": null,
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member1/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": {
+            "uri": temp_dir.url().join("workspace/member1/deno.json").unwrap(),
+          },
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member1/package.json").unwrap(),
+          },
+        },
+        {
+          "scopeUri": temp_dir.url().join("workspace/member2/").unwrap(),
+          "workspaceRootScopeUri": temp_dir.url().join("workspace/").unwrap(),
+          "denoJson": null,
+          "packageJson": {
+            "uri": temp_dir.url().join("workspace/member2/package.json").unwrap(),
+          },
+        },
+      ],
+    }),
+  );
+  client.shutdown();
+}
+
 #[test]
 fn lsp_did_change_deno_configuration_notification() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
@@ -1342,6 +1527,7 @@ fn lsp_import_map_import_completions() {
         "/#/": "./src/",
         "fs": "https://example.com/fs/index.js",
         "std/": "https://example.com/std@0.123.0/",
+        "lib/": "./lib/",
       },
       "scopes": {
         "file:///": {
@@ -1364,17 +1550,18 @@ fn lsp_import_map_import_completions() {
       "uri": uri,
       "languageId": "typescript",
       "version": 1,
-      "text": "import * as a from \"/~/b.ts\";\nimport * as b from \"\""
-    }
+      "text": r#"
+        import * as b from "";
+        import * as b from "/~/";
+        import * as b from "lib/";
+      "#,
+    },
   }));
 
   let res = client.get_completion(
     &uri,
-    (1, 20),
-    json!({
-      "triggerKind": 2,
-      "triggerCharacter": "\""
-    }),
+    (1, 28),
+    json!({ "triggerKind": 2, "triggerCharacter": "\"" }),
   );
   assert_eq!(
     json!(res),
@@ -1409,6 +1596,13 @@ fn lsp_import_map_import_completions() {
           "sortText": "std",
           "insertText": "std",
           "commitCharacters": ["\"", "'"],
+        }, {
+          "label": "lib",
+          "kind": 19,
+          "detail": "(import map)",
+          "sortText": "lib",
+          "insertText": "lib",
+          "commitCharacters": ["\"", "'"],
         }, {
           "label": "fs",
           "kind": 17,
@@ -1435,32 +1629,10 @@ fn lsp_import_map_import_completions() {
     })
   );
 
-  client.write_notification(
-    "textDocument/didChange",
-    json!({
-      "textDocument": {
-        "uri": uri,
-        "version": 2
-      },
-      "contentChanges": [
-        {
-          "range": {
-            "start": { "line": 1, "character": 20 },
-            "end": { "line": 1, "character": 20 }
-          },
-          "text": "/~/"
-        }
-      ]
-    }),
-  );
-
   let res = client.get_completion(
-    uri,
-    (1, 23),
-    json!({
-      "triggerKind": 2,
-      "triggerCharacter": "/"
-    }),
+    &uri,
+    (2, 31),
+    json!({ "triggerKind": 2, "triggerCharacter": "/" }),
   );
   assert_eq!(
     json!(res),
@@ -1475,15 +1647,44 @@ fn lsp_import_map_import_completions() {
           "filterText": "/~/b.ts",
           "textEdit": {
             "range": {
-              "start": { "line": 1, "character": 20 },
-              "end": { "line": 1, "character": 23 }
+              "start": { "line": 2, "character": 28 },
+              "end": { "line": 2, "character": 31 },
             },
-            "newText": "/~/b.ts"
+            "newText": "/~/b.ts",
           },
           "commitCharacters": ["\"", "'"],
-        }
-      ]
-    })
+        },
+      ],
+    }),
+  );
+
+  let res = client.get_completion(
+    &uri,
+    (3, 32),
+    json!({ "triggerKind": 2, "triggerCharacter": "/" }),
+  );
+  assert_eq!(
+    json!(res),
+    json!({
+      "isIncomplete": false,
+      "items": [
+        {
+          "label": "b.ts",
+          "kind": 17,
+          "detail": "(local)",
+          "sortText": "1",
+          "filterText": "lib/b.ts",
+          "textEdit": {
+            "range": {
+              "start": { "line": 3, "character": 28 },
+              "end": { "line": 3, "character": 32 },
+            },
+            "newText": "lib/b.ts",
+          },
+          "commitCharacters": ["\"", "'"],
+        },
+      ],
+    }),
   );
 
   client.shutdown();
@@ -1626,15 +1827,41 @@ fn lsp_hover_disabled() {
 fn lsp_inlay_hints() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
   let mut client = context.new_lsp_command().build();
-  client.initialize(|builder| {
-    builder.enable_inlay_hints();
-  });
+  client.initialize_default();
+  client.change_configuration(json!({
+    "deno": {
+      "enable": true,
+    },
+    "typescript": {
+      "inlayHints": {
+        "parameterNames": {
+          "enabled": "all",
+        },
+        "parameterTypes": {
+          "enabled": true,
+        },
+        "variableTypes": {
+          "enabled": true,
+        },
+        "propertyDeclarationTypes": {
+          "enabled": true,
+        },
+        "functionLikeReturnTypes": {
+          "enabled": true,
+        },
+        "enumMemberValues": {
+          "enabled": true,
+        },
+      },
+    },
+  }));
   client.did_open(json!({
     "textDocument": {
       "uri": "file:///a/file.ts",
       "languageId": "typescript",
       "version": 1,
-      "text": r#"function a(b: string) {
+      "text": r#"
+        function a(b: string) {
           return b;
         }
 
@@ -1653,8 +1880,19 @@ fn lsp_inlay_hints() {
         }
 
         ["a"].map((v) => v + v);
-        "#
-    }
+
+        interface Bar {
+          someField: string;
+        }
+        function getBar(): Bar {
+          return { someField: "foo" };
+        }
+        // This shouldn't have a type hint because the variable name makes it
+        // redundant.
+        const bar = getBar();
+        const someValue = getBar();
+      "#,
+    },
   }));
   let res = client.write_request(
     "textDocument/inlayHint",
@@ -1663,65 +1901,130 @@ fn lsp_inlay_hints() {
         "uri": "file:///a/file.ts",
       },
       "range": {
-        "start": { "line": 0, "character": 0 },
-        "end": { "line": 19, "character": 0, }
-      }
+        "start": { "line": 1, "character": 0 },
+        "end": { "line": 31, "character": 0, },
+      },
     }),
   );
   assert_eq!(
     res,
     json!([
       {
-        "position": { "line": 0, "character": 21 },
-        "label": ": string",
+        "position": { "line": 1, "character": 29 },
+        "label": [{ "value": ": " }, { "value": "string" }],
         "kind": 1,
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 4, "character": 10 },
-        "label": "b:",
+        "position": { "line": 5, "character": 10 },
+        "label": [
+          {
+            "value": "b",
+            "location": {
+              "uri": "file:///a/file.ts",
+              "range": {
+                "start": { "line": 1, "character": 19 },
+                "end": { "line": 1, "character": 20 },
+              },
+            },
+          },
+          { "value": ":" },
+        ],
         "kind": 2,
-        "paddingRight": true
+        "paddingRight": true,
       }, {
-        "position": { "line": 7, "character": 11 },
+        "position": { "line": 8, "character": 11 },
         "label": "= 0",
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 10, "character": 17 },
-        "label": "string:",
+        "position": { "line": 11, "character": 17 },
+        "label": [
+          {
+            "value": "string",
+            "location": {
+              "uri": "deno:/asset/lib.es5.d.ts",
+              "range": {
+                "start": { "line": 41, "character": 26 },
+                "end": { "line": 41, "character": 32 },
+              },
+            },
+          },
+          { "value": ":" },
+        ],
         "kind": 2,
-        "paddingRight": true
+        "paddingRight": true,
       }, {
-        "position": { "line": 10, "character": 24 },
-        "label": "radix:",
+        "position": { "line": 11, "character": 24 },
+        "label": [
+          {
+            "value": "radix",
+            "location": {
+              "uri": "deno:/asset/lib.es5.d.ts",
+              "range": {
+                "start": { "line": 41, "character": 42 },
+                "end": { "line": 41, "character": 47 },
+              },
+            },
+          },
+          { "value": ":" },
+        ],
         "kind": 2,
-        "paddingRight": true
+        "paddingRight": true,
       }, {
-        "position": { "line": 12, "character": 15 },
-        "label": ": number",
+        "position": { "line": 13, "character": 15 },
+        "label": [{ "value": ": " }, { "value": "number" }],
         "kind": 1,
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 15, "character": 11 },
-        "label": ": number",
+        "position": { "line": 16, "character": 11 },
+        "label": [{ "value": ": " }, { "value": "number" }],
         "kind": 1,
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 18, "character": 18 },
-        "label": "callbackfn:",
+        "position": { "line": 19, "character": 18 },
+        "label": [
+          {
+            "value": "callbackfn",
+            "location": {
+              "uri": "deno:/asset/lib.es5.d.ts",
+              "range": {
+                "start": { "line": 1462, "character": 11 },
+                "end": { "line": 1462, "character": 21 },
+              },
+            },
+          },
+          { "value": ":" },
+        ],
         "kind": 2,
-        "paddingRight": true
+        "paddingRight": true,
       }, {
-        "position": { "line": 18, "character": 20 },
-        "label": ": string",
+        "position": { "line": 19, "character": 20 },
+        "label": [{ "value": ": " }, { "value": "string" }],
         "kind": 1,
-        "paddingLeft": true
+        "paddingLeft": true,
       }, {
-        "position": { "line": 18, "character": 21 },
-        "label": ": string",
+        "position": { "line": 19, "character": 21 },
+        "label": [{ "value": ": " }, { "value": "string" }],
         "kind": 1,
-        "paddingLeft": true
-      }
-    ])
+        "paddingLeft": true,
+      }, {
+        "position": { "line": 30, "character": 23 },
+        "label": [
+          { "value": ": " },
+          {
+            "value": "Bar",
+            "location": {
+              "uri": "file:///a/file.ts",
+              "range": {
+                "start": { "line": 21, "character": 18 },
+                "end": { "line": 21, "character": 21 },
+              },
+            },
+          },
+        ],
+        "kind": 1,
+        "paddingLeft": true,
+      },
+    ]),
   );
   client.shutdown();
 }
@@ -5652,7 +5955,7 @@ fn lsp_jsr_code_action_missing_declaration() {
                       "character": 6,
                     },
                   },
-                  "newText": "import type { ReturnType } from \"jsr:@denotest/types-file/types\";\n",
+                  "newText": "import { ReturnType } from \"jsr:@denotest/types-file/types\";\n",
                 },
                 {
                   "range": {
@@ -6166,6 +6469,16 @@ fn lsp_code_actions_imports() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
   let mut client = context.new_lsp_command().build();
   client.initialize_default();
+  client.change_configuration(json!({
+    "deno": {
+      "enable": true,
+    },
+    "typescript": {
+      "preferences": {
+        "preferTypeOnlyAutoImports": true,
+      },
+    },
+  }));
   client.did_open(json!({
       "textDocument": {
         "uri": "file:///a/file00.ts",
@@ -6465,7 +6778,7 @@ fn lsp_code_actions_imports_dts() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 },
             },
-            "newText": "import type { SomeType } from \"./decl.d.ts\";\n",
+            "newText": "import { SomeType } from \"./decl.d.ts\";\n",
           }],
         }],
       },
@@ -6474,6 +6787,117 @@ fn lsp_code_actions_imports_dts() {
   client.shutdown();
 }
 
+#[test]
+fn lsp_code_actions_import_map_remap() {
+  let context = TestContextBuilder::new().use_temp_cwd().build();
+  let temp_dir = context.temp_dir();
+  temp_dir.write(
+    "deno.json",
+    json!({
+      "imports": {
+        "foo": "./foo.ts",
+        "bar": "./bar.ts",
+      },
+    })
+    .to_string(),
+  );
+  temp_dir.write("foo.ts", "");
+  temp_dir.write("bar.ts", "");
+  let mut client = context.new_lsp_command().build();
+  client.initialize_default();
+  let diagnostics = client.did_open(json!({
+    "textDocument": {
+      "uri": temp_dir.url().join("file.ts").unwrap(),
+      "languageId": "typescript",
+      "version": 1,
+      "text": r#"
+        import "./foo.ts";
+        import type {} from "./bar.ts";
+      "#,
+    }
+  }));
+  let res = client.write_request(
+    "textDocument/codeAction",
+    json!({
+      "textDocument": { "uri": temp_dir.url().join("file.ts").unwrap() },
+      "range": {
+        "start": { "line": 0, "character": 0 },
+        "end": { "line": 3, "character": 0 },
+      },
+      "context": {
+        "diagnostics": diagnostics.all(),
+        "only": ["quickfix"],
+      },
+    }),
+  );
+  assert_eq!(
+    res,
+    json!([
+      {
+        "title": "Update \"./foo.ts\" to \"foo\" to use import map.",
+        "kind": "quickfix",
+        "diagnostics": [
+          {
+            "range": {
+              "start": { "line": 1, "character": 15 },
+              "end": { "line": 1, "character": 25 },
+            },
+            "severity": 4,
+            "code": "import-map-remap",
+            "source": "deno",
+            "message": "The import specifier can be remapped to \"foo\" which will resolve it via the active import map.",
+            "data": { "from": "./foo.ts", "to": "foo" },
+          },
+        ],
+        "edit": {
+          "changes": {
+            temp_dir.url().join("file.ts").unwrap(): [
+              {
+                "range": {
+                  "start": { "line": 1, "character": 15 },
+                  "end": { "line": 1, "character": 25 },
+                },
+                "newText": "\"foo\"",
+              },
+            ],
+          },
+        },
+      },
+      {
+        "title": "Update \"./bar.ts\" to \"bar\" to use import map.",
+        "kind": "quickfix",
+        "diagnostics": [
+          {
+            "range": {
+              "start": { "line": 2, "character": 28 },
+              "end": { "line": 2, "character": 38 },
+            },
+            "severity": 4,
+            "code": "import-map-remap",
+            "source": "deno",
+            "message": "The import specifier can be remapped to \"bar\" which will resolve it via the active import map.",
+            "data": { "from": "./bar.ts", "to": "bar" },
+          },
+        ],
+        "edit": {
+          "changes": {
+            temp_dir.url().join("file.ts").unwrap(): [
+              {
+                "range": {
+                  "start": { "line": 2, "character": 28 },
+                  "end": { "line": 2, "character": 38 },
+                },
+                "newText": "\"bar\"",
+              },
+            ],
+          },
+        },
+      },
+    ]),
+  );
+  client.shutdown();
+}
+
 #[test]
 fn lsp_code_actions_refactor() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
@@ -6785,7 +7209,7 @@ fn lsp_code_actions_imports_respects_fmt_config() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 }
             },
-            "newText": "import type { DuckConfigOptions } from './file01.ts'\n"
+            "newText": "import { DuckConfigOptions } from './file01.ts'\n"
           }]
         }]
       }
@@ -6838,7 +7262,7 @@ fn lsp_code_actions_imports_respects_fmt_config() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 }
             },
-            "newText": "import type { DuckConfigOptions } from './file01.ts'\n"
+            "newText": "import { DuckConfigOptions } from './file01.ts'\n"
           }]
         }]
       },
@@ -6938,7 +7362,7 @@ fn lsp_quote_style_from_workspace_settings() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 },
             },
-            "newText": "import type { DuckConfigOptions } from './file01.ts';\n",
+            "newText": "import { DuckConfigOptions } from './file01.ts';\n",
           }],
         }],
       },
@@ -6982,7 +7406,7 @@ fn lsp_quote_style_from_workspace_settings() {
               "start": { "line": 0, "character": 0 },
               "end": { "line": 0, "character": 0 },
             },
-            "newText": "import type { DuckConfigOptions } from \"./file01.ts\";\n",
+            "newText": "import { DuckConfigOptions } from \"./file01.ts\";\n",
           }],
         }],
       },
@@ -9387,14 +9811,15 @@ fn lsp_auto_discover_registry() {
       "triggerCharacter": "@"
     }),
   );
-  let (method, res) = client.read_notification();
-  assert_eq!(method, "deno/registryState");
+  let res = client
+    .read_notification_with_method::<Value>("deno/registryState")
+    .unwrap();
   assert_eq!(
     res,
-    Some(json!({
+    json!({
       "origin": "http://localhost:4545",
       "suggestions": true,
-    }))
+    }),
   );
   client.shutdown();
 }
@@ -10101,7 +10526,6 @@ fn lsp_diagnostics_refresh_dependents() {
   assert_eq!(json!(diagnostics.all()), json!([])); // no diagnostics now
 
   client.shutdown();
-  assert_eq!(client.queue_len(), 0);
 }
 
 // Regression test for https://github.com/denoland/deno/issues/10897.
@@ -15060,25 +15484,23 @@ fn lsp_sloppy_imports() {
 fn lsp_sloppy_imports_prefers_dts() {
   let context = TestContextBuilder::new().use_temp_cwd().build();
   let temp_dir = context.temp_dir();
-  let temp_dir = temp_dir.path();
-
-  temp_dir
-    .join("deno.json")
-    .write(r#"{ "unstable": ["sloppy-imports"] }"#);
-
-  let mut client: LspClient = context
-    .new_lsp_command()
-    .set_root_dir(temp_dir.clone())
-    .build();
-  client.initialize_default();
-
-  temp_dir.join("a.js").write("export const foo: number;");
-
-  let a_dts = source_file(temp_dir.join("a.d.ts"), "export const foo = 3;");
+  temp_dir.write("deno.json", json!({}).to_string());
+  temp_dir.write("a.js", "export const foo: number;");
+  let a_dts =
+    source_file(temp_dir.path().join("a.d.ts"), "export const foo = 3;");
   let file = source_file(
-    temp_dir.join("file.ts"),
+    temp_dir.path().join("file.ts"),
     "import { foo } from './a.js';\nconsole.log(foo);",
   );
+  let mut client: LspClient = context.new_lsp_command().build();
+  client.initialize_default();
+  client.change_configuration(json!({
+    "deno": {
+      "enable": true,
+      "unstable": ["sloppy-imports"],
+    },
+  }));
+
   let diagnostics = client.did_open_file(&file);
   // no other warnings because "a.js" exists
   assert_eq!(
diff --git a/tests/integration/node_unit_tests.rs b/tests/integration/node_unit_tests.rs
index d66db5a40e..40bd7b2fbb 100644
--- a/tests/integration/node_unit_tests.rs
+++ b/tests/integration/node_unit_tests.rs
@@ -212,3 +212,7 @@ itest!(unhandled_rejection_web_process {
   envs: env_vars_for_npm_tests(),
   http_server: true,
 });
+
+// !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
+// The itest macro is deprecated. Please move your new test to ~/tests/specs.
+// !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
diff --git a/tests/integration/npm_tests.rs b/tests/integration/npm_tests.rs
index f47b1bdd4a..f8c6eebf39 100644
--- a/tests/integration/npm_tests.rs
+++ b/tests/integration/npm_tests.rs
@@ -876,7 +876,7 @@ fn auto_discover_lock_file() {
     .run();
   output
     .assert_matches_text(
-r#"Download http://localhost:4260/@denotest/bin
+r#"Download http://localhost:4260/@denotest%2fbin
 error: Integrity check failed for package: "npm:@denotest/bin@1.0.0". Unable to verify that the package
 is the same as when the lockfile was generated.
 
@@ -1058,10 +1058,10 @@ fn reload_info_not_found_cache_but_exists_remote() {
     .run();
   output.assert_matches_text(concat!(
     "[UNORDERED_START]\n",
-    "Download http://localhost:4260/@denotest/esm-basic\n",
-    "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-    "Download http://localhost:4260/@denotest/cjs-default-export\n",
-    "Download http://localhost:4260/@denotest/cjs-default-export/1.0.0.tgz\n",
+    "Download http://localhost:4260/@denotest%2fesm-basic\n",
+    "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+    "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
+    "Download http://localhost:4260/@denotestcjs-default-export/1.0.0.tgz\n",
     "Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz\n",
     "Download http://localhost:4260/@denotest/esm-import-cjs-default/1.0.0.tgz\n",
     "[UNORDERED_END]\n",
@@ -1088,8 +1088,8 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
       "[UNORDERED_END]\n",
       "Node esm importing node cjs\n[WILDCARD]",
     ));
@@ -1120,8 +1120,8 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
       "[UNORDERED_END]\n",
       "Node esm importing node cjs\n[WILDCARD]",
     ));
@@ -1159,8 +1159,8 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
       "[UNORDERED_END]\n",
       "[UNORDERED_START]\n",
       "Initialize @denotest/cjs-default-export@1.0.0\n",
@@ -1196,9 +1196,9 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/esm-basic\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-basic\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
       "[UNORDERED_END]\n",
       "Initialize @denotest/esm-basic@1.0.0\n",
       "Node esm importing node cjs\n[WILDCARD]",
@@ -1237,9 +1237,9 @@ fn reload_info_not_found_cache_but_exists_remote() {
     let output = test_context.new_command().args("run main.ts").run();
     output.assert_matches_text(concat!(
       "[UNORDERED_START]\n",
-      "Download http://localhost:4260/@denotest/cjs-default-export\n",
-      "Download http://localhost:4260/@denotest/esm-basic\n",
-      "Download http://localhost:4260/@denotest/esm-import-cjs-default\n",
+      "Download http://localhost:4260/@denotest%2fcjs-default-export\n",
+      "Download http://localhost:4260/@denotest%2fesm-basic\n",
+      "Download http://localhost:4260/@denotest%2fesm-import-cjs-default\n",
       "[UNORDERED_END]\n",
       "Node esm importing node cjs\n[WILDCARD]",
     ));
@@ -1419,7 +1419,7 @@ fn top_level_install_package_json_explicit_opt_in() {
   temp_dir.write("main.ts", "console.log(5);");
   let output = test_context.new_command().args("cache main.ts").run();
   output.assert_matches_text(concat!(
-    "Download http://localhost:4260/@denotest/esm-basic\n",
+    "Download http://localhost:4260/@denotest%2fesm-basic\n",
     "Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz\n",
     "Initialize @denotest/esm-basic@1.0.0\n",
   ));
diff --git a/tests/integration/repl_tests.rs b/tests/integration/repl_tests.rs
index 4e00398ce6..9eceb2f05d 100644
--- a/tests/integration/repl_tests.rs
+++ b/tests/integration/repl_tests.rs
@@ -255,6 +255,20 @@ fn console_log() {
     console.write_line("'world'");
     console.expect("\"world\"");
   });
+
+  // https://github.com/denoland/deno/issues/21428
+  let (out, err) = util::run_and_collect_output_with_args(
+    true,
+    vec![
+      "repl",
+      "--eval-file=./../specs/repl/console_log/093_console_log_format.js",
+    ],
+    None,
+    None,
+    false,
+  );
+  assert_contains!(out, "0.5");
+  assert!(err.is_empty());
 }
 
 #[test]
diff --git a/tests/integration/run_tests.rs b/tests/integration/run_tests.rs
index ca24f18f46..a07dd56c83 100644
--- a/tests/integration/run_tests.rs
+++ b/tests/integration/run_tests.rs
@@ -898,7 +898,7 @@ fn lock_redirects() {
     .run()
     .assert_matches_text(concat!(
       "Download http://localhost:4545/echo.ts\n",
-      "Download http://localhost:4260/@denotest/esm-basic\n",
+      "Download http://localhost:4260/@denotest%2fesm-basic\n",
       "Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz\n",
       "Hi, there",
     ));
@@ -3605,7 +3605,8 @@ fn running_declaration_files() {
     temp_dir.write(file, "");
     context
       .new_command()
-      .args_vec(["run", file])
+      // todo(dsherret): investigate why --allow-read is required here
+      .args_vec(["run", "--allow-read", file])
       .run()
       .skip_output_check()
       .assert_exit_code(0);
diff --git a/tests/integration/watcher_tests.rs b/tests/integration/watcher_tests.rs
index 122353bba9..d4705b8d53 100644
--- a/tests/integration/watcher_tests.rs
+++ b/tests/integration/watcher_tests.rs
@@ -566,6 +566,76 @@ async fn run_watch_no_dynamic() {
   check_alive_then_kill(child);
 }
 
+#[flaky_test(tokio)]
+async fn serve_watch_all() {
+  let t = TempDir::new();
+  let main_file_to_watch = t.path().join("main_file_to_watch.js");
+  main_file_to_watch.write(
+    "export default {
+      fetch(_request: Request) {
+        return new Response(\"aaaaaaqqq!\");
+      },
+    };",
+  );
+
+  let mut child = util::deno_cmd()
+    .current_dir(t.path())
+    .arg("serve")
+    .arg("--watch=another_file.js")
+    .arg("-L")
+    .arg("debug")
+    .arg(&main_file_to_watch)
+    .env("NO_COLOR", "1")
+    .piped_output()
+    .spawn()
+    .unwrap();
+  let (mut stdout_lines, mut stderr_lines) = child_lines(&mut child);
+
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+
+  // Change content of the file
+  main_file_to_watch.write(
+    "export default {
+      fetch(_request: Request) {
+        return new Response(\"aaaaaaqqq123!\");
+      },
+    };",
+  );
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+
+  let another_file = t.path().join("another_file.js");
+  another_file.write("export const foo = 0;");
+  // Confirm that the added file is watched as well
+  wait_contains("Restarting", &mut stderr_lines).await;
+
+  main_file_to_watch
+    .write("import { foo } from './another_file.js'; console.log(foo);");
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_contains("0", &mut stdout_lines).await;
+
+  another_file.write("export const foo = 42;");
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_contains("42", &mut stdout_lines).await;
+
+  // Confirm that watch continues even with wrong syntax error
+  another_file.write("syntax error ^^");
+
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_contains("error:", &mut stderr_lines).await;
+
+  main_file_to_watch.write(
+    "export default {
+      fetch(_request: Request) {
+        return new Response(\"aaaaaaqqq!\");
+      },
+    };",
+  );
+  wait_contains("Restarting", &mut stderr_lines).await;
+  wait_for_watcher("main_file_to_watch.js", &mut stderr_lines).await;
+  check_alive_then_kill(child);
+}
+
 #[flaky_test(tokio)]
 async fn run_watch_npm_specifier() {
   let _g = util::http_server();
diff --git a/tests/napi/callback_test.js b/tests/napi/callback_test.js
index 98622d48d1..c132fefa18 100644
--- a/tests/napi/callback_test.js
+++ b/tests/napi/callback_test.js
@@ -1,6 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-import { assertEquals, loadTestLibrary } from "./common.js";
+import { assertEquals, assertThrows, loadTestLibrary } from "./common.js";
 
 const callback = loadTestLibrary();
 
@@ -36,3 +36,12 @@ Deno.test("napi callback run with args & recv", function () {
   );
   assertEquals(result, 69);
 });
+
+Deno.test("napi callback handles errors correctly", function () {
+  const e = new Error("hi!");
+  assertThrows(() => {
+    callback.test_callback_throws(() => {
+      throw e;
+    });
+  }, e);
+});
diff --git a/tests/napi/object_test.js b/tests/napi/object_test.js
index 4bc5c3c9c4..6226b0138c 100644
--- a/tests/napi/object_test.js
+++ b/tests/napi/object_test.js
@@ -1,6 +1,11 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-import { assert, assertEquals, loadTestLibrary } from "./common.js";
+import {
+  assert,
+  assertEquals,
+  assertThrows,
+  loadTestLibrary,
+} from "./common.js";
 
 const object = loadTestLibrary();
 
@@ -12,4 +17,22 @@ Deno.test("napi object", function () {
 
   const r1 = object.test_object_get(r);
   assert(r === r1);
+
+  const r2 = object.test_object_attr_property(r);
+  assert(r === r2);
+  assertThrows(
+    () => {
+      r2.self = "2";
+    },
+    Error,
+    "Cannot assign to read only property 'self' of object '#<Object>'",
+  );
+
+  assertThrows(
+    () => {
+      r2.method = () => {};
+    },
+    Error,
+    "Cannot assign to read only property 'method' of object '#<Object>'",
+  );
 });
diff --git a/tests/napi/src/async.rs b/tests/napi/src/async.rs
index 3d3827b51c..367d2e9ef0 100644
--- a/tests/napi/src/async.rs
+++ b/tests/napi/src/async.rs
@@ -95,7 +95,7 @@ extern "C" fn test_async_work(
   ));
   let mut baton = unsafe { Box::from_raw(baton_ptr as *mut Baton) };
   baton.task = async_work;
-  Box::into_raw(baton);
+  let _ = Box::into_raw(baton);
   assert_napi_ok!(napi_queue_async_work(env, async_work));
 
   ptr::null_mut()
diff --git a/tests/napi/src/callback.rs b/tests/napi/src/callback.rs
index 8909f51768..2512f6a38f 100644
--- a/tests/napi/src/callback.rs
+++ b/tests/napi/src/callback.rs
@@ -8,6 +8,7 @@ use napi_sys::ValueType::napi_object;
 use napi_sys::ValueType::napi_undefined;
 use napi_sys::*;
 use std::ptr;
+use Status::napi_pending_exception;
 
 /// `test_callback_run((a, b) => a + b, [1, 2])` => 3
 extern "C" fn test_callback_run(
@@ -98,6 +99,34 @@ extern "C" fn test_callback_run_with_recv(
   result
 }
 
+extern "C" fn test_callback_throws(
+  env: napi_env,
+  info: napi_callback_info,
+) -> napi_value {
+  let (args, ..) = napi_get_callback_info!(env, info, 1);
+
+  let mut global: napi_value = ptr::null_mut();
+  assert_napi_ok!(napi_get_global(env, &mut global));
+
+  let mut argv = vec![];
+  let mut result: napi_value = ptr::null_mut();
+  assert_eq!(
+    unsafe {
+      napi_call_function(
+        env,
+        global,  // recv
+        args[0], // cb
+        argv.len(),
+        argv.as_mut_ptr(),
+        &mut result,
+      )
+    },
+    napi_pending_exception
+  );
+
+  result
+}
+
 pub fn init(env: napi_env, exports: napi_value) {
   let properties = &[
     napi_new_property!(env, "test_callback_run", test_callback_run),
@@ -106,6 +135,7 @@ pub fn init(env: napi_env, exports: napi_value) {
       "test_callback_run_with_recv",
       test_callback_run_with_recv
     ),
+    napi_new_property!(env, "test_callback_throws", test_callback_throws),
   ];
 
   assert_napi_ok!(napi_define_properties(
diff --git a/tests/napi/src/object.rs b/tests/napi/src/object.rs
index aa34133dcf..9876f4dae0 100644
--- a/tests/napi/src/object.rs
+++ b/tests/napi/src/object.rs
@@ -40,10 +40,39 @@ extern "C" fn test_object_get(
   obj
 }
 
+extern "C" fn test_object_attr_property(
+  env: napi_env,
+  info: napi_callback_info,
+) -> napi_value {
+  let (args, argc, _) = napi_get_callback_info!(env, info, 1);
+  assert_eq!(argc, 1);
+
+  let obj = args[0];
+  let mut property = napi_new_property!(env, "self", test_object_new);
+  property.attributes = PropertyAttributes::enumerable;
+  property.method = None;
+  property.value = obj;
+  let mut method_property = napi_new_property!(env, "method", test_object_new);
+  method_property.attributes = PropertyAttributes::enumerable;
+  let properties = &[property, method_property];
+  assert_napi_ok!(napi_define_properties(
+    env,
+    obj,
+    properties.len(),
+    properties.as_ptr()
+  ));
+  obj
+}
+
 pub fn init(env: napi_env, exports: napi_value) {
   let properties = &[
     napi_new_property!(env, "test_object_new", test_object_new),
     napi_new_property!(env, "test_object_get", test_object_get),
+    napi_new_property!(
+      env,
+      "test_object_attr_property",
+      test_object_attr_property
+    ),
   ];
 
   assert_napi_ok!(napi_define_properties(
diff --git a/tests/napi/src/tsfn.rs b/tests/napi/src/tsfn.rs
index dabc96f835..a3a231cec1 100644
--- a/tests/napi/src/tsfn.rs
+++ b/tests/napi/src/tsfn.rs
@@ -46,6 +46,7 @@ fn create_custom_gc(env: sys::napi_env) {
     "Create async resource string in napi_register_module_v1 napi_register_module_v1"
   );
   let mut custom_gc_tsfn = ptr::null_mut();
+  let context = Box::into_raw(Box::new(0)) as *mut c_void;
   check_status_or_panic!(
     unsafe {
       sys::napi_create_threadsafe_function(
@@ -57,7 +58,7 @@ fn create_custom_gc(env: sys::napi_env) {
         1,
         ptr::null_mut(),
         Some(custom_gc_finalize),
-        ptr::null_mut(),
+        context,
         Some(custom_gc),
         &mut custom_gc_tsfn,
       )
@@ -80,8 +81,9 @@ unsafe extern "C" fn empty(
 unsafe extern "C" fn custom_gc_finalize(
   _env: sys::napi_env,
   _finalize_data: *mut c_void,
-  _finalize_hint: *mut c_void,
+  finalize_hint: *mut c_void,
 ) {
+  let _ = Box::from_raw(finalize_hint as *mut i32);
 }
 
 extern "C" fn custom_gc(
diff --git a/tests/node_compat/config.jsonc b/tests/node_compat/config.jsonc
index bc9bf476be..16951d9ede 100644
--- a/tests/node_compat/config.jsonc
+++ b/tests/node_compat/config.jsonc
@@ -43,9 +43,6 @@
       // TODO(littledivy): windows ipc streams not yet implemented
       "test-child-process-fork-ref.js",
       "test-child-process-fork-ref2.js",
-      // TODO(bartlomieju): this test is very flaky on CI
-      // https://github.com/denoland/deno/issues/25855
-      // "test-child-process-ipc-next-tick.js",
       "test-child-process-ipc.js",
       "test-child-process-spawnsync-env.js",
       "test-child-process-stdio-inherit.js",
@@ -90,8 +87,6 @@
       "test-net-server-try-ports.js",
       "test-net-socket-timeout.js",
       "test-net-write-arguments.js",
-      // TODO(nathanwhit): Disable os.userInfo is slightly incorrect
-      // "test-os.js",
       "test-path-resolve.js",
       "test-querystring.js",
       "test-readline-interface.js",
@@ -240,6 +235,7 @@
       "test-child-process-execfilesync-maxbuf.js",
       "test-child-process-execsync-maxbuf.js",
       "test-child-process-flush-stdio.js",
+      "test-child-process-ipc-next-tick.js",
       "test-child-process-kill.js",
       "test-child-process-set-blocking.js",
       "test-child-process-spawn-args.js",
@@ -439,6 +435,7 @@
       "test-net-server-unref.js",
       "test-net-socket-destroy-twice.js",
       "test-net-socket-no-halfopen-enforcer.js",
+      "test-net-socket-setnodelay.js",
       "test-net-timeout-no-handle.js",
       "test-net-write-arguments.js",
       "test-next-tick-doesnt-hang.js",
@@ -449,6 +446,7 @@
       "test-next-tick-when-exiting.js",
       "test-next-tick.js",
       "test-nodeeventtarget.js",
+      "test-os.js",
       "test-outgoing-message-destroy.js",
       "test-outgoing-message-pipe.js",
       "test-parse-args.mjs",
diff --git a/tests/node_compat/runner/TODO.md b/tests/node_compat/runner/TODO.md
index 99258f5a56..231a4f62c9 100644
--- a/tests/node_compat/runner/TODO.md
+++ b/tests/node_compat/runner/TODO.md
@@ -280,7 +280,6 @@ NOTE: This file should not be manually edited. Please edit `tests/node_compat/co
 - [parallel/test-child-process-fork3.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-fork3.js)
 - [parallel/test-child-process-http-socket-leak.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-http-socket-leak.js)
 - [parallel/test-child-process-internal.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-internal.js)
-- [parallel/test-child-process-ipc-next-tick.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-ipc-next-tick.js)
 - [parallel/test-child-process-ipc.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-ipc.js)
 - [parallel/test-child-process-no-deprecation.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-no-deprecation.js)
 - [parallel/test-child-process-pipe-dataflow.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-child-process-pipe-dataflow.js)
@@ -1851,7 +1850,6 @@ NOTE: This file should not be manually edited. Please edit `tests/node_compat/co
 - [parallel/test-net-socket-ready-without-cb.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-ready-without-cb.js)
 - [parallel/test-net-socket-reset-send.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-reset-send.js)
 - [parallel/test-net-socket-reset-twice.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-reset-twice.js)
-- [parallel/test-net-socket-setnodelay.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-setnodelay.js)
 - [parallel/test-net-socket-timeout-unref.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-timeout-unref.js)
 - [parallel/test-net-socket-timeout.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-timeout.js)
 - [parallel/test-net-socket-write-after-close.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-net-socket-write-after-close.js)
@@ -1880,7 +1878,6 @@ NOTE: This file should not be manually edited. Please edit `tests/node_compat/co
 - [parallel/test-os-homedir-no-envvar.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-os-homedir-no-envvar.js)
 - [parallel/test-os-process-priority.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-os-process-priority.js)
 - [parallel/test-os-userinfo-handles-getter-errors.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-os-userinfo-handles-getter-errors.js)
-- [parallel/test-os.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-os.js)
 - [parallel/test-path-posix-relative-on-windows.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-path-posix-relative-on-windows.js)
 - [parallel/test-pending-deprecation.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-pending-deprecation.js)
 - [parallel/test-perf-gc-crash.js](https://github.com/nodejs/node/tree/v18.12.1/test/parallel/test-perf-gc-crash.js)
diff --git a/tests/node_compat/test/parallel/test-child-process-ipc-next-tick.js b/tests/node_compat/test/parallel/test-child-process-ipc-next-tick.js
new file mode 100644
index 0000000000..f511d25004
--- /dev/null
+++ b/tests/node_compat/test/parallel/test-child-process-ipc-next-tick.js
@@ -0,0 +1,46 @@
+// deno-fmt-ignore-file
+// deno-lint-ignore-file
+
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+// Taken from Node 18.12.1
+// This file is automatically generated by `tests/node_compat/runner/setup.ts`. Do not modify this file manually.
+
+'use strict';
+const common = require('../common');
+const assert = require('assert');
+const cp = require('child_process');
+const NUM_MESSAGES = 10;
+const values = [];
+
+for (let i = 0; i < NUM_MESSAGES; ++i) {
+  values[i] = i;
+}
+
+if (process.argv[2] === 'child') {
+  const received = values.map(() => { return false; });
+
+  process.on('uncaughtException', common.mustCall((err) => {
+    received[err] = true;
+    const done = received.every((element) => { return element === true; });
+
+    if (done)
+      process.disconnect();
+  }, NUM_MESSAGES));
+
+  process.on('message', (msg) => {
+    // If messages are handled synchronously, throwing should break the IPC
+    // message processing.
+    throw msg;
+  });
+
+  process.send('ready');
+} else {
+  const child = cp.fork(__filename, ['child']);
+
+  child.on('message', common.mustCall((msg) => {
+    assert.strictEqual(msg, 'ready');
+    values.forEach((value) => {
+      child.send(value);
+    });
+  }));
+}
diff --git a/tests/node_compat/test/parallel/test-net-socket-setnodelay.js b/tests/node_compat/test/parallel/test-net-socket-setnodelay.js
new file mode 100644
index 0000000000..3d11b84528
--- /dev/null
+++ b/tests/node_compat/test/parallel/test-net-socket-setnodelay.js
@@ -0,0 +1,63 @@
+// deno-fmt-ignore-file
+// deno-lint-ignore-file
+
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+// Taken from Node 18.12.1
+// This file is automatically generated by `tests/node_compat/runner/setup.ts`. Do not modify this file manually.
+
+'use strict';
+
+const common = require('../common');
+const assert = require('assert');
+const net = require('net');
+
+const truthyValues = [true, 1, 'true', {}, []];
+const falseyValues = [false, 0, ''];
+const genSetNoDelay = (desiredArg) => (enable) => {
+  assert.strictEqual(enable, desiredArg);
+};
+
+// setNoDelay should default to true
+let socket = new net.Socket({
+  handle: {
+    setNoDelay: common.mustCall(genSetNoDelay(true)),
+    readStart() {}
+  }
+});
+socket.setNoDelay();
+
+socket = new net.Socket({
+  handle: {
+    setNoDelay: common.mustCall(genSetNoDelay(true), 1),
+    readStart() {}
+  }
+});
+truthyValues.forEach((testVal) => socket.setNoDelay(testVal));
+
+socket = new net.Socket({
+  handle: {
+    setNoDelay: common.mustNotCall(),
+    readStart() {}
+  }
+});
+falseyValues.forEach((testVal) => socket.setNoDelay(testVal));
+
+socket = new net.Socket({
+  handle: {
+    setNoDelay: common.mustCall(3),
+    readStart() {}
+  }
+});
+truthyValues.concat(falseyValues).concat(truthyValues)
+  .forEach((testVal) => socket.setNoDelay(testVal));
+
+// If a handler doesn't have a setNoDelay function it shouldn't be called.
+// In the case below, if it is called an exception will be thrown
+socket = new net.Socket({
+  handle: {
+    setNoDelay: null,
+    readStart() {}
+  }
+});
+const returned = socket.setNoDelay(true);
+assert.ok(returned instanceof net.Socket);
diff --git a/tests/node_compat/test/parallel/test-os.js b/tests/node_compat/test/parallel/test-os.js
new file mode 100644
index 0000000000..f7c24342ad
--- /dev/null
+++ b/tests/node_compat/test/parallel/test-os.js
@@ -0,0 +1,286 @@
+// deno-fmt-ignore-file
+// deno-lint-ignore-file
+
+// Copyright Joyent and Node contributors. All rights reserved. MIT license.
+// Taken from Node 18.12.1
+// This file is automatically generated by `tests/node_compat/runner/setup.ts`. Do not modify this file manually.
+
+// Copyright Joyent, Inc. and other Node contributors.
+//
+// Permission is hereby granted, free of charge, to any person obtaining a
+// copy of this software and associated documentation files (the
+// "Software"), to deal in the Software without restriction, including
+// without limitation the rights to use, copy, modify, merge, publish,
+// distribute, sublicense, and/or sell copies of the Software, and to permit
+// persons to whom the Software is furnished to do so, subject to the
+// following conditions:
+//
+// The above copyright notice and this permission notice shall be included
+// in all copies or substantial portions of the Software.
+//
+// THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS
+// OR IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF
+// MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN
+// NO EVENT SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM,
+// DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR
+// OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE
+// USE OR OTHER DEALINGS IN THE SOFTWARE.
+
+'use strict';
+const common = require('../common');
+const assert = require('assert');
+const os = require('os');
+const path = require('path');
+const { inspect } = require('util');
+
+const is = {
+  number: (value, key) => {
+    assert(!Number.isNaN(value), `${key} should not be NaN`);
+    assert.strictEqual(typeof value, 'number');
+  },
+  string: (value) => { assert.strictEqual(typeof value, 'string'); },
+  array: (value) => { assert.ok(Array.isArray(value)); },
+  object: (value) => {
+    assert.strictEqual(typeof value, 'object');
+    assert.notStrictEqual(value, null);
+  }
+};
+
+process.env.TMPDIR = '/tmpdir';
+process.env.TMP = '/tmp';
+process.env.TEMP = '/temp';
+if (common.isWindows) {
+  assert.strictEqual(os.tmpdir(), '/temp');
+  process.env.TEMP = '';
+  assert.strictEqual(os.tmpdir(), '/tmp');
+  process.env.TMP = '';
+  const expected = `${process.env.SystemRoot || process.env.windir}\\temp`;
+  assert.strictEqual(os.tmpdir(), expected);
+  process.env.TEMP = '\\temp\\';
+  assert.strictEqual(os.tmpdir(), '\\temp');
+  process.env.TEMP = '\\tmpdir/';
+  assert.strictEqual(os.tmpdir(), '\\tmpdir/');
+  process.env.TEMP = '\\';
+  assert.strictEqual(os.tmpdir(), '\\');
+  process.env.TEMP = 'C:\\';
+  assert.strictEqual(os.tmpdir(), 'C:\\');
+} else {
+  assert.strictEqual(os.tmpdir(), '/tmpdir');
+  process.env.TMPDIR = '';
+  assert.strictEqual(os.tmpdir(), '/tmp');
+  process.env.TMP = '';
+  assert.strictEqual(os.tmpdir(), '/temp');
+  process.env.TEMP = '';
+  assert.strictEqual(os.tmpdir(), '/tmp');
+  process.env.TMPDIR = '/tmpdir/';
+  assert.strictEqual(os.tmpdir(), '/tmpdir');
+  process.env.TMPDIR = '/tmpdir\\';
+  assert.strictEqual(os.tmpdir(), '/tmpdir\\');
+  process.env.TMPDIR = '/';
+  assert.strictEqual(os.tmpdir(), '/');
+}
+
+const endianness = os.endianness();
+is.string(endianness);
+assert.match(endianness, /[BL]E/);
+
+const hostname = os.hostname();
+is.string(hostname);
+assert.ok(hostname.length > 0);
+
+// IBMi process priority is different.
+if (!common.isIBMi) {
+  const DUMMY_PRIORITY = 10;
+  os.setPriority(DUMMY_PRIORITY);
+  const priority = os.getPriority();
+  is.number(priority);
+  assert.strictEqual(priority, DUMMY_PRIORITY);
+}
+
+// On IBMi, os.uptime() returns 'undefined'
+if (!common.isIBMi) {
+  const uptime = os.uptime();
+  is.number(uptime);
+  assert.ok(uptime > 0);
+}
+
+const cpus = os.cpus();
+is.array(cpus);
+assert.ok(cpus.length > 0);
+for (const cpu of cpus) {
+  assert.strictEqual(typeof cpu.model, 'string');
+  assert.strictEqual(typeof cpu.speed, 'number');
+  assert.strictEqual(typeof cpu.times.user, 'number');
+  assert.strictEqual(typeof cpu.times.nice, 'number');
+  assert.strictEqual(typeof cpu.times.sys, 'number');
+  assert.strictEqual(typeof cpu.times.idle, 'number');
+  assert.strictEqual(typeof cpu.times.irq, 'number');
+}
+
+const type = os.type();
+is.string(type);
+assert.ok(type.length > 0);
+
+const release = os.release();
+is.string(release);
+assert.ok(release.length > 0);
+// TODO: Check format on more than just AIX
+if (common.isAIX)
+  assert.match(release, /^\d+\.\d+$/);
+
+const platform = os.platform();
+is.string(platform);
+assert.ok(platform.length > 0);
+
+const arch = os.arch();
+is.string(arch);
+assert.ok(arch.length > 0);
+
+if (!common.isSunOS) {
+  // not implemented yet
+  assert.ok(os.loadavg().length > 0);
+  assert.ok(os.freemem() > 0);
+  assert.ok(os.totalmem() > 0);
+}
+
+const interfaces = os.networkInterfaces();
+switch (platform) {
+  case 'linux': {
+    const filter = (e) =>
+      e.address === '127.0.0.1' &&
+      e.netmask === '255.0.0.0';
+
+    const actual = interfaces.lo.filter(filter);
+    const expected = [{
+      address: '127.0.0.1',
+      netmask: '255.0.0.0',
+      family: 'IPv4',
+      mac: '00:00:00:00:00:00',
+      internal: true,
+      cidr: '127.0.0.1/8'
+    }];
+    assert.deepStrictEqual(actual, expected);
+    break;
+  }
+  case 'win32': {
+    const filter = (e) =>
+      e.address === '127.0.0.1';
+
+    const actual = interfaces['Loopback Pseudo-Interface 1'].filter(filter);
+    const expected = [{
+      address: '127.0.0.1',
+      netmask: '255.0.0.0',
+      family: 'IPv4',
+      mac: '00:00:00:00:00:00',
+      internal: true,
+      cidr: '127.0.0.1/8'
+    }];
+    assert.deepStrictEqual(actual, expected);
+    break;
+  }
+}
+const netmaskToCIDRSuffixMap = new Map(Object.entries({
+  '255.0.0.0': 8,
+  '255.255.255.0': 24,
+  'ffff:ffff:ffff:ffff::': 64,
+  'ffff:ffff:ffff:ffff:ffff:ffff:ffff:ffff': 128
+}));
+
+Object.values(interfaces)
+  .flat(Infinity)
+  .map((v) => ({ v, mask: netmaskToCIDRSuffixMap.get(v.netmask) }))
+  .forEach(({ v, mask }) => {
+    assert.ok('cidr' in v, `"cidr" prop not found in ${inspect(v)}`);
+    if (mask) {
+      assert.strictEqual(v.cidr, `${v.address}/${mask}`);
+    }
+  });
+
+const EOL = os.EOL;
+if (common.isWindows) {
+  assert.strictEqual(EOL, '\r\n');
+} else {
+  assert.strictEqual(EOL, '\n');
+}
+
+const home = os.homedir();
+is.string(home);
+assert.ok(home.includes(path.sep));
+
+const version = os.version();
+assert.strictEqual(typeof version, 'string');
+assert(version);
+
+if (common.isWindows && process.env.USERPROFILE) {
+  assert.strictEqual(home, process.env.USERPROFILE);
+  delete process.env.USERPROFILE;
+  assert.ok(os.homedir().includes(path.sep));
+  process.env.USERPROFILE = home;
+} else if (!common.isWindows && process.env.HOME) {
+  assert.strictEqual(home, process.env.HOME);
+  delete process.env.HOME;
+  assert.ok(os.homedir().includes(path.sep));
+  process.env.HOME = home;
+}
+
+const pwd = os.userInfo();
+is.object(pwd);
+const pwdBuf = os.userInfo({ encoding: 'buffer' });
+
+if (common.isWindows) {
+  assert.strictEqual(pwd.uid, -1);
+  assert.strictEqual(pwd.gid, -1);
+  assert.strictEqual(pwd.shell, null);
+  assert.strictEqual(pwdBuf.uid, -1);
+  assert.strictEqual(pwdBuf.gid, -1);
+  assert.strictEqual(pwdBuf.shell, null);
+} else {
+  is.number(pwd.uid);
+  is.number(pwd.gid);
+  assert.strictEqual(typeof pwd.shell, 'string');
+  // It's possible for /etc/passwd to leave the user's shell blank.
+  if (pwd.shell.length > 0) {
+    assert(pwd.shell.includes(path.sep));
+  }
+  assert.strictEqual(pwd.uid, pwdBuf.uid);
+  assert.strictEqual(pwd.gid, pwdBuf.gid);
+  assert.strictEqual(pwd.shell, pwdBuf.shell.toString('utf8'));
+}
+
+is.string(pwd.username);
+assert.ok(pwd.homedir.includes(path.sep));
+assert.strictEqual(pwd.username, pwdBuf.username.toString('utf8'));
+assert.strictEqual(pwd.homedir, pwdBuf.homedir.toString('utf8'));
+
+assert.strictEqual(`${os.hostname}`, os.hostname());
+assert.strictEqual(`${os.homedir}`, os.homedir());
+assert.strictEqual(`${os.release}`, os.release());
+assert.strictEqual(`${os.type}`, os.type());
+assert.strictEqual(`${os.endianness}`, os.endianness());
+assert.strictEqual(`${os.tmpdir}`, os.tmpdir());
+assert.strictEqual(`${os.arch}`, os.arch());
+assert.strictEqual(`${os.platform}`, os.platform());
+assert.strictEqual(`${os.version}`, os.version());
+assert.strictEqual(`${os.machine}`, os.machine());
+assert.strictEqual(+os.totalmem, os.totalmem());
+
+// Assert that the following values are coercible to numbers.
+// On IBMi, os.uptime() returns 'undefined'
+if (!common.isIBMi) {
+  is.number(+os.uptime, 'uptime');
+  is.number(os.uptime(), 'uptime');
+}
+
+is.number(+os.availableParallelism, 'availableParallelism');
+is.number(os.availableParallelism(), 'availableParallelism');
+is.number(+os.freemem, 'freemem');
+is.number(os.freemem(), 'freemem');
+
+const devNull = os.devNull;
+if (common.isWindows) {
+  assert.strictEqual(devNull, '\\\\.\\nul');
+} else {
+  assert.strictEqual(devNull, '/dev/null');
+}
+
+assert.ok(os.availableParallelism() > 0);
diff --git a/tests/registry/jsr/@denotest/multiple-exports/1.0.0/add.ts b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/add.ts
new file mode 100644
index 0000000000..de02f69024
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/add.ts
@@ -0,0 +1 @@
+export * from "jsr:@denotest/add@1";
diff --git a/tests/registry/jsr/@denotest/multiple-exports/1.0.0/data.json b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/data.json
new file mode 100644
index 0000000000..885e71c6cc
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/data.json
@@ -0,0 +1,3 @@
+{
+  "a": 1
+}
\ No newline at end of file
diff --git a/tests/registry/jsr/@denotest/multiple-exports/1.0.0/subtract.ts b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/subtract.ts
new file mode 100644
index 0000000000..215c42310d
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/1.0.0/subtract.ts
@@ -0,0 +1 @@
+export * from "jsr:@denotest/subtract@1";
diff --git a/tests/registry/jsr/@denotest/multiple-exports/1.0.0_meta.json b/tests/registry/jsr/@denotest/multiple-exports/1.0.0_meta.json
new file mode 100644
index 0000000000..d9f58b9a61
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/1.0.0_meta.json
@@ -0,0 +1,7 @@
+{
+  "exports": {
+    "./add": "./add.ts",
+    "./subtract": "./subtract.ts",
+    "./data-json": "./data.json"
+  }
+}
diff --git a/tests/registry/jsr/@denotest/multiple-exports/meta.json b/tests/registry/jsr/@denotest/multiple-exports/meta.json
new file mode 100644
index 0000000000..02601e4d0d
--- /dev/null
+++ b/tests/registry/jsr/@denotest/multiple-exports/meta.json
@@ -0,0 +1,5 @@
+{
+  "versions": {
+    "1.0.0": {}
+  }
+}
diff --git a/tests/registry/jsr/@denotest/type-only-import/1.0.0/foo.ts b/tests/registry/jsr/@denotest/type-only-import/1.0.0/foo.ts
new file mode 100644
index 0000000000..4e09512c03
--- /dev/null
+++ b/tests/registry/jsr/@denotest/type-only-import/1.0.0/foo.ts
@@ -0,0 +1,3 @@
+export interface Foo {
+  bar: string;
+}
\ No newline at end of file
diff --git a/tests/registry/jsr/@denotest/type-only-import/1.0.0/mod.ts b/tests/registry/jsr/@denotest/type-only-import/1.0.0/mod.ts
new file mode 100644
index 0000000000..093a57d8a1
--- /dev/null
+++ b/tests/registry/jsr/@denotest/type-only-import/1.0.0/mod.ts
@@ -0,0 +1,3 @@
+import type { Foo } from "./foo.ts";
+
+export const foo: Foo = { bar: "foo" };
\ No newline at end of file
diff --git a/tests/registry/jsr/@denotest/type-only-import/1.0.0_meta.json b/tests/registry/jsr/@denotest/type-only-import/1.0.0_meta.json
new file mode 100644
index 0000000000..631a18d0e5
--- /dev/null
+++ b/tests/registry/jsr/@denotest/type-only-import/1.0.0_meta.json
@@ -0,0 +1,5 @@
+{
+  "exports": {
+    ".": "./mod.ts"
+  }
+}
diff --git a/tests/registry/jsr/@denotest/type-only-import/meta.json b/tests/registry/jsr/@denotest/type-only-import/meta.json
new file mode 100644
index 0000000000..02601e4d0d
--- /dev/null
+++ b/tests/registry/jsr/@denotest/type-only-import/meta.json
@@ -0,0 +1,5 @@
+{
+  "versions": {
+    "1.0.0": {}
+  }
+}
diff --git a/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.d.mts b/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.d.mts
new file mode 100644
index 0000000000..29da1e6d7b
--- /dev/null
+++ b/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.d.mts
@@ -0,0 +1,3 @@
+export declare function setValue(val: number): void;
+export declare function getValue(): number;
+export declare const url: string;
diff --git a/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.mjs b/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.mjs
new file mode 100644
index 0000000000..0a44f75859
--- /dev/null
+++ b/tests/registry/npm-private3/@denotest3/basic/1.0.0/main.mjs
@@ -0,0 +1,11 @@
+let value = 0;
+
+export function setValue(newValue) {
+  value = newValue;
+}
+
+export function getValue() {
+  return value;
+}
+
+export const url = import.meta.url;
diff --git a/tests/registry/npm-private3/@denotest3/basic/1.0.0/other.mjs b/tests/registry/npm-private3/@denotest3/basic/1.0.0/other.mjs
new file mode 100644
index 0000000000..00ed99da45
--- /dev/null
+++ b/tests/registry/npm-private3/@denotest3/basic/1.0.0/other.mjs
@@ -0,0 +1,3 @@
+export function hello() {
+    return "hello, world!";
+}
\ No newline at end of file
diff --git a/tests/registry/npm-private3/@denotest3/basic/1.0.0/package.json b/tests/registry/npm-private3/@denotest3/basic/1.0.0/package.json
new file mode 100644
index 0000000000..ce6ea33830
--- /dev/null
+++ b/tests/registry/npm-private3/@denotest3/basic/1.0.0/package.json
@@ -0,0 +1,7 @@
+{
+  "name": "@denotest3/basic",
+  "version": "1.0.0",
+  "type": "module",
+  "main": "main.mjs",
+  "types": "main.d.mts"
+}
diff --git a/tests/registry/npm/@denotest/better-say-hello/1.0.0/say-hello.js b/tests/registry/npm/@denotest/better-say-hello/1.0.0/say-hello.js
index 0b8d63cf48..5243d49026 100644
--- a/tests/registry/npm/@denotest/better-say-hello/1.0.0/say-hello.js
+++ b/tests/registry/npm/@denotest/better-say-hello/1.0.0/say-hello.js
@@ -1,2 +1,2 @@
 import { sayBetterHello } from "./index.js";
-sayBetterHello();
\ No newline at end of file
+sayBetterHello();
diff --git a/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/package.json b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/package.json
new file mode 100644
index 0000000000..43f07a2351
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/package.json
@@ -0,0 +1,8 @@
+{
+  "name": "@denotest/cjs-multiple-exports",
+  "version": "1.0.0",
+  "exports": {
+    ".": "./src/index.js",
+    "./add": "./src/add.js"
+  }
+}
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/add.js b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/add.js
new file mode 100644
index 0000000000..42c8a7c604
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/add.js
@@ -0,0 +1,3 @@
+module.exports = function add(a, b) {
+  return a + b;
+};
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/index.js b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/index.js
new file mode 100644
index 0000000000..432ed652ed
--- /dev/null
+++ b/tests/registry/npm/@denotest/cjs-multiple-exports/1.0.0/src/index.js
@@ -0,0 +1,3 @@
+module.exports = {
+  hello: "world"
+};
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/index.js b/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/index.js
index 4eb9b107a0..242fe92f57 100644
--- a/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/index.js
+++ b/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/index.js
@@ -1,5 +1,3 @@
-modules.export = {
+module.exports = {
   value: 42
 };
-
-console.log('index.js', modules.export.value);
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/package.json b/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/package.json
index 3c6fa005fe..085ab6414a 100644
--- a/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/package.json
+++ b/tests/registry/npm/@denotest/node-lifecycle-scripts/1.0.0/package.json
@@ -6,6 +6,7 @@
     "install": "echo install && cli-esm 'hello from install script'",
     "postinstall": "echo postinstall && npx cowsay postinstall"
   },
+  "exports": "./index.js",
   "dependencies": {
     "@denotest/bin": "1.0.0"
   }
diff --git a/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/index.js b/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/index.js
new file mode 100644
index 0000000000..b835b8e25e
--- /dev/null
+++ b/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/index.js
@@ -0,0 +1,2 @@
+#!/usr/bin/env node
+console.log(`npm_config_user_agent: ${process.env["npm_config_user_agent"]}`);
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/package.json b/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/package.json
new file mode 100644
index 0000000000..9071173467
--- /dev/null
+++ b/tests/registry/npm/@denotest/print-npm-user-agent/1.0.0/package.json
@@ -0,0 +1,10 @@
+{
+  "name": "@denotest/print-npm-user-agent",
+  "version": "1.0.0",
+  "bin": {
+    "print-npm-user-agent": "index.js"
+  },
+  "scripts": {
+    "postinstall": "echo postinstall && node index.js && exit 1"
+  }
+}
\ No newline at end of file
diff --git a/tests/registry/npm/@denotest/say-hello/1.0.0/say-hello.js b/tests/registry/npm/@denotest/say-hello/1.0.0/say-hello.js
index 8751b8e47b..66d02cde56 100644
--- a/tests/registry/npm/@denotest/say-hello/1.0.0/say-hello.js
+++ b/tests/registry/npm/@denotest/say-hello/1.0.0/say-hello.js
@@ -1,2 +1,5 @@
 import { sayHello } from "./index.js";
-console.log(sayHello());
\ No newline at end of file
+console.log(sayHello());
+import path from "node:path";
+import fs from "node:fs";
+fs.writeSync(fs.openSync(path.join(process.env.INIT_CWD, "say-hello-output.txt"), "w"), sayHello());
diff --git a/tests/registry/npm/@denotest/type-commonjs/1.0.0/index.js b/tests/registry/npm/@denotest/type-commonjs/1.0.0/index.js
index cb0ff5c3b5..d3f80a0495 100644
--- a/tests/registry/npm/@denotest/type-commonjs/1.0.0/index.js
+++ b/tests/registry/npm/@denotest/type-commonjs/1.0.0/index.js
@@ -1 +1,5 @@
-export {};
+// this module is declared as CommonJS, but during loading we'll
+// discover it's ESM and load it fine
+export function add(a, b) {
+  return a + b;
+}
diff --git a/tests/specs/add/alias/__test__.jsonc b/tests/specs/add/alias/__test__.jsonc
new file mode 100644
index 0000000000..8a16ad3b46
--- /dev/null
+++ b/tests/specs/add/alias/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "args": "install my-alias@npm:@denotest/add",
+    "output": "[WILDCARD]"
+  }, {
+    "args": [
+      "eval",
+      "console.log(Deno.readTextFileSync('package.json').trim())"
+    ],
+    "output": "package.json.out"
+  }]
+}
diff --git a/tests/specs/add/alias/package.json b/tests/specs/add/alias/package.json
new file mode 100644
index 0000000000..9664f260a7
--- /dev/null
+++ b/tests/specs/add/alias/package.json
@@ -0,0 +1,4 @@
+{
+  "dependencies": {
+  }
+}
diff --git a/tests/specs/add/alias/package.json.out b/tests/specs/add/alias/package.json.out
new file mode 100644
index 0000000000..b6326e8bfb
--- /dev/null
+++ b/tests/specs/add/alias/package.json.out
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "my-alias": "npm:@denotest/add@^1.0.0"
+  }
+}
diff --git a/tests/specs/add/comments_deno_json/__test__.jsonc b/tests/specs/add/comments_deno_json/__test__.jsonc
new file mode 100644
index 0000000000..7197eb473f
--- /dev/null
+++ b/tests/specs/add/comments_deno_json/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "add npm:@denotest/esm-basic jsr:@denotest/add",
+      "output": "[WILDCARD]"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('deno.jsonc').trim())"
+      ],
+      "output": "deno.jsonc.out"
+    }
+  ]
+}
diff --git a/tests/specs/add/comments_deno_json/deno.jsonc b/tests/specs/add/comments_deno_json/deno.jsonc
new file mode 100644
index 0000000000..6a37b343d9
--- /dev/null
+++ b/tests/specs/add/comments_deno_json/deno.jsonc
@@ -0,0 +1,7 @@
+// Testing four space indents too
+// deno-fmt-ignore
+{
+    "imports": {
+        "@denotest/add2": "npm:@denotest/add" // some comment
+    }
+}
diff --git a/tests/specs/add/comments_deno_json/deno.jsonc.out b/tests/specs/add/comments_deno_json/deno.jsonc.out
new file mode 100644
index 0000000000..0cca35c64c
--- /dev/null
+++ b/tests/specs/add/comments_deno_json/deno.jsonc.out
@@ -0,0 +1,9 @@
+// Testing four space indents too
+// deno-fmt-ignore
+{
+    "imports": {
+        "@denotest/add": "jsr:@denotest/add@^1.0.0",
+        "@denotest/add2": "npm:@denotest/add", // some comment
+        "@denotest/esm-basic": "npm:@denotest/esm-basic@^1.0.0"
+    }
+}
diff --git a/tests/specs/add/dev/add.out b/tests/specs/add/dev/add.out
index 42161f3ae1..44bd9cac7e 100644
--- a/tests/specs/add/dev/add.out
+++ b/tests/specs/add/dev/add.out
@@ -1,4 +1,4 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/add/exact_version/__test__.jsonc b/tests/specs/add/exact_version/__test__.jsonc
new file mode 100644
index 0000000000..feb6cc6172
--- /dev/null
+++ b/tests/specs/add/exact_version/__test__.jsonc
@@ -0,0 +1,35 @@
+{
+  "tempDir": true,
+  "tests": {
+    "npm": {
+      "steps": [
+        {
+          "args": "add npm:@denotest/esm-basic@1.0.0",
+          "output": "npm_add.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('deno.json').trim())"
+          ],
+          "output": "npm_deno.json.out"
+        }
+      ]
+    },
+    "jsr": {
+      "steps": [
+        {
+          "args": "add jsr:@denotest/add@1.0.0",
+          "output": "jsr_add.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('deno.json').trim())"
+          ],
+          "output": "jsr_deno.json.out"
+        }
+      ]
+    }
+  }
+}
diff --git a/tests/specs/add/exact_version/deno.json b/tests/specs/add/exact_version/deno.json
new file mode 100644
index 0000000000..0967ef424b
--- /dev/null
+++ b/tests/specs/add/exact_version/deno.json
@@ -0,0 +1 @@
+{}
diff --git a/tests/specs/add/exact_version/jsr_add.out b/tests/specs/add/exact_version/jsr_add.out
new file mode 100644
index 0000000000..f2684ef57e
--- /dev/null
+++ b/tests/specs/add/exact_version/jsr_add.out
@@ -0,0 +1,2 @@
+Add jsr:@denotest/add@1.0.0
+Download http://127.0.0.1:4250/@denotest/add/1.0.0/mod.ts
diff --git a/tests/specs/add/exact_version/jsr_deno.json.out b/tests/specs/add/exact_version/jsr_deno.json.out
new file mode 100644
index 0000000000..7f1715bd78
--- /dev/null
+++ b/tests/specs/add/exact_version/jsr_deno.json.out
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/add": "jsr:@denotest/add@1.0.0"
+  }
+}
diff --git a/tests/specs/add/exact_version/npm_add.out b/tests/specs/add/exact_version/npm_add.out
new file mode 100644
index 0000000000..2f73e5afb5
--- /dev/null
+++ b/tests/specs/add/exact_version/npm_add.out
@@ -0,0 +1,3 @@
+Add npm:@denotest/esm-basic@1.0.0
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/add/exact_version/npm_deno.json.out b/tests/specs/add/exact_version/npm_deno.json.out
new file mode 100644
index 0000000000..ff4afa772b
--- /dev/null
+++ b/tests/specs/add/exact_version/npm_deno.json.out
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/esm-basic": "npm:@denotest/esm-basic@1.0.0"
+  }
+}
diff --git a/tests/specs/add/existing_deps_singleline/__test__.jsonc b/tests/specs/add/existing_deps_singleline/__test__.jsonc
new file mode 100644
index 0000000000..8a6ef1a5fa
--- /dev/null
+++ b/tests/specs/add/existing_deps_singleline/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "add npm:@denotest/esm-basic",
+      "output": "[WILDCARD]"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('package.json').trim())"
+      ],
+      "output": "package.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/add/existing_deps_singleline/package.json b/tests/specs/add/existing_deps_singleline/package.json
new file mode 100644
index 0000000000..3677a6e2e8
--- /dev/null
+++ b/tests/specs/add/existing_deps_singleline/package.json
@@ -0,0 +1,3 @@
+{
+  "dependencies": { "cowsay": "*" }
+}
diff --git a/tests/specs/add/existing_deps_singleline/package.json.out b/tests/specs/add/existing_deps_singleline/package.json.out
new file mode 100644
index 0000000000..5a7fa36805
--- /dev/null
+++ b/tests/specs/add/existing_deps_singleline/package.json.out
@@ -0,0 +1,6 @@
+{
+  "dependencies": {
+    "@denotest/esm-basic": "^1.0.0",
+    "cowsay": "*"
+  }
+}
diff --git a/tests/specs/add/exiting_dev_deps/__test__.jsonc b/tests/specs/add/exiting_dev_deps/__test__.jsonc
new file mode 100644
index 0000000000..8a6ef1a5fa
--- /dev/null
+++ b/tests/specs/add/exiting_dev_deps/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "add npm:@denotest/esm-basic",
+      "output": "[WILDCARD]"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('package.json').trim())"
+      ],
+      "output": "package.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/add/exiting_dev_deps/package.json b/tests/specs/add/exiting_dev_deps/package.json
new file mode 100644
index 0000000000..e7b8c50618
--- /dev/null
+++ b/tests/specs/add/exiting_dev_deps/package.json
@@ -0,0 +1,5 @@
+{
+  "devDependencies": {
+    "cowsay": "*"
+  }
+}
diff --git a/tests/specs/add/exiting_dev_deps/package.json.out b/tests/specs/add/exiting_dev_deps/package.json.out
new file mode 100644
index 0000000000..9bff99bc28
--- /dev/null
+++ b/tests/specs/add/exiting_dev_deps/package.json.out
@@ -0,0 +1,8 @@
+{
+  "dependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  },
+  "devDependencies": {
+    "cowsay": "*"
+  }
+}
diff --git a/tests/specs/add/jsr_prefers_deno_json/__test__.jsonc b/tests/specs/add/jsr_prefers_deno_json/__test__.jsonc
new file mode 100644
index 0000000000..ca9c4b4d9d
--- /dev/null
+++ b/tests/specs/add/jsr_prefers_deno_json/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "add jsr:@denotest/add",
+      "output": "add.out"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('./deno.json').trim())"
+      ],
+      "output": "deno.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/add/jsr_prefers_deno_json/add.out b/tests/specs/add/jsr_prefers_deno_json/add.out
new file mode 100644
index 0000000000..cb8140c6db
--- /dev/null
+++ b/tests/specs/add/jsr_prefers_deno_json/add.out
@@ -0,0 +1,3 @@
+Created deno.json configuration file.
+Add jsr:@denotest/add@1.0.0
+Download [WILDCARD]
diff --git a/tests/specs/add/jsr_prefers_deno_json/deno.json.out b/tests/specs/add/jsr_prefers_deno_json/deno.json.out
new file mode 100644
index 0000000000..38ca2d4b85
--- /dev/null
+++ b/tests/specs/add/jsr_prefers_deno_json/deno.json.out
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/add": "jsr:@denotest/add@^1.0.0"
+  }
+}
diff --git a/tests/specs/add/jsr_prefers_deno_json/package.json b/tests/specs/add/jsr_prefers_deno_json/package.json
new file mode 100644
index 0000000000..0967ef424b
--- /dev/null
+++ b/tests/specs/add/jsr_prefers_deno_json/package.json
@@ -0,0 +1 @@
+{}
diff --git a/tests/specs/add/only_unstable_versions/add.out b/tests/specs/add/only_unstable_versions/add.out
index 48462b8bea..8bd8d93038 100644
--- a/tests/specs/add/only_unstable_versions/add.out
+++ b/tests/specs/add/only_unstable_versions/add.out
@@ -1,3 +1,3 @@
 Add npm:@denotest/unstable@1.0.0-beta.1
-Download http://localhost:4260/@denotest/unstable
+Download http://localhost:4260/@denotest%2funstable
 Download http://localhost:4260/@denotest/unstable/1.0.0-beta.1.tgz
diff --git a/tests/specs/add/package_json_and_deno_json/__test__.jsonc b/tests/specs/add/package_json_and_deno_json/__test__.jsonc
index 0beee02d15..8d67a07c82 100644
--- a/tests/specs/add/package_json_and_deno_json/__test__.jsonc
+++ b/tests/specs/add/package_json_and_deno_json/__test__.jsonc
@@ -41,6 +41,29 @@
           "output": "good\n"
         }
       ]
+    },
+    "only_prefers_package_json_if_closer": {
+      "steps": [
+        {
+          "cwd": "./subdir",
+          "args": "add npm:@denotest/esm-basic jsr:@denotest/add npm:@denotest/say-hello",
+          "output": "[WILDCARD]"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('package.json').trim())"
+          ],
+          "output": "{}\n"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('./subdir/deno.json').trim())"
+          ],
+          "output": "subdir/prefer_if_closer_deno.json.out"
+        }
+      ]
     }
   }
 }
diff --git a/tests/specs/add/package_json_and_deno_json/add.out b/tests/specs/add/package_json_and_deno_json/add.out
index 5577a55acc..4ce7bb8ee1 100644
--- a/tests/specs/add/package_json_and_deno_json/add.out
+++ b/tests/specs/add/package_json_and_deno_json/add.out
@@ -2,9 +2,9 @@
 Add npm:@denotest/esm-basic@1.0.0
 Add jsr:@denotest/add@1.0.0
 Add npm:@denotest/say-hello@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
-Download http://localhost:4260/@denotest/say-hello
+Download http://localhost:4260/@denotest%2fsay-hello
 Download http://localhost:4260/@denotest/say-hello/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Initialize @denotest/say-hello@1.0.0
diff --git a/tests/specs/add/package_json_and_deno_json/add_esm_basic.out b/tests/specs/add/package_json_and_deno_json/add_esm_basic.out
index 42161f3ae1..44bd9cac7e 100644
--- a/tests/specs/add/package_json_and_deno_json/add_esm_basic.out
+++ b/tests/specs/add/package_json_and_deno_json/add_esm_basic.out
@@ -1,4 +1,4 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/add/package_json_and_deno_json/subdir/deno.json b/tests/specs/add/package_json_and_deno_json/subdir/deno.json
new file mode 100644
index 0000000000..cc54bbd8a2
--- /dev/null
+++ b/tests/specs/add/package_json_and_deno_json/subdir/deno.json
@@ -0,0 +1,4 @@
+{
+  "name": "@test/subdir",
+  "exports": "./mod.ts"
+}
diff --git a/tests/specs/add/package_json_and_deno_json/subdir/mod.ts b/tests/specs/add/package_json_and_deno_json/subdir/mod.ts
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/tests/specs/add/package_json_and_deno_json/subdir/prefer_if_closer_deno.json.out b/tests/specs/add/package_json_and_deno_json/subdir/prefer_if_closer_deno.json.out
new file mode 100644
index 0000000000..8a5819d503
--- /dev/null
+++ b/tests/specs/add/package_json_and_deno_json/subdir/prefer_if_closer_deno.json.out
@@ -0,0 +1,9 @@
+{
+  "name": "@test/subdir",
+  "exports": "./mod.ts",
+  "imports": {
+    "@denotest/add": "jsr:@denotest/add@^1.0.0",
+    "@denotest/esm-basic": "npm:@denotest/esm-basic@^1.0.0",
+    "@denotest/say-hello": "npm:@denotest/say-hello@^1.0.0"
+  }
+}
diff --git a/tests/specs/add/update_lockfile_if_package_json/__test__.jsonc b/tests/specs/add/update_lockfile_if_package_json/__test__.jsonc
new file mode 100644
index 0000000000..80b35dc3c2
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/__test__.jsonc
@@ -0,0 +1,31 @@
+{
+  "tempDir": true,
+  "tests": {
+    "updates_lockfile": {
+      "steps": [
+        {
+          "args": "add npm:@denotest/esm-basic npm:@denotest/say-hello",
+          "output": "add.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('deno.lock'))"
+          ],
+          "output": "lockfile_add.out"
+        },
+        {
+          "args": "remove @denotest/esm-basic @denotest/say-hello",
+          "output": "remove.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('deno.lock'))"
+          ],
+          "output": "lockfile_remove.out"
+        }
+      ]
+    }
+  }
+}
diff --git a/tests/specs/add/update_lockfile_if_package_json/add.out b/tests/specs/add/update_lockfile_if_package_json/add.out
new file mode 100644
index 0000000000..97989b0c38
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/add.out
@@ -0,0 +1,5 @@
+[UNORDERED_START]
+Add npm:@denotest/esm-basic@1.0.0
+Add npm:@denotest/say-hello@1.0.0
+[UNORDERED_END]
+[WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/add/update_lockfile_if_package_json/lockfile_add.out b/tests/specs/add/update_lockfile_if_package_json/lockfile_add.out
new file mode 100644
index 0000000000..d452c2de82
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/lockfile_add.out
@@ -0,0 +1,7 @@
+{
+  "version": "4",
+  "specifiers": {
+    "npm:@denotest/esm-basic@1": "1.0.0",
+    "npm:@denotest/say-hello@1": "1.0.0"
+  },
+[WILDCARD]
diff --git a/tests/specs/add/update_lockfile_if_package_json/lockfile_remove.out b/tests/specs/add/update_lockfile_if_package_json/lockfile_remove.out
new file mode 100644
index 0000000000..fdd4f1cc60
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/lockfile_remove.out
@@ -0,0 +1,4 @@
+{
+  "version": "4"
+}
+
diff --git a/tests/specs/add/update_lockfile_if_package_json/package.json b/tests/specs/add/update_lockfile_if_package_json/package.json
new file mode 100644
index 0000000000..e69de29bb2
diff --git a/tests/specs/add/update_lockfile_if_package_json/remove.out b/tests/specs/add/update_lockfile_if_package_json/remove.out
new file mode 100644
index 0000000000..8efb0810cf
--- /dev/null
+++ b/tests/specs/add/update_lockfile_if_package_json/remove.out
@@ -0,0 +1,4 @@
+[UNORDERED_START]
+Removed @denotest/esm-basic
+Removed @denotest/say-hello
+[UNORDERED_END]
diff --git a/tests/specs/bench/package_json/install.out b/tests/specs/bench/package_json/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/bench/package_json/install.out
+++ b/tests/specs/bench/package_json/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/cache/package_json/main.cache.out b/tests/specs/cache/package_json/main.cache.out
index f5a1cd15ee..af6bcb03b3 100644
--- a/tests/specs/cache/package_json/main.cache.out
+++ b/tests/specs/cache/package_json/main.cache.out
@@ -1,2 +1,2 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/check/cjs_default_export/main.out b/tests/specs/check/cjs_default_export/main.out
index f284593a19..6c5f18b632 100644
--- a/tests/specs/check/cjs_default_export/main.out
+++ b/tests/specs/check/cjs_default_export/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/cjs-default-export
+Download http://localhost:4260/@denotest%2fcjs-default-export
 Download http://localhost:4260/@denotest/cjs-default-export/1.0.0.tgz
 Check file:///[WILDCARD]/main.ts
 error: TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
diff --git a/tests/specs/check/css_import/exists_run_with_check.out b/tests/specs/check/css_import/exists_run_with_check.out
index 1a1dafeb74..315769e40c 100644
--- a/tests/specs/check/css_import/exists_run_with_check.out
+++ b/tests/specs/check/css_import/exists_run_with_check.out
@@ -1,3 +1,3 @@
-error: Expected a JavaScript or TypeScript module, but identified a Unknown module. Importing these types of modules is currently not supported.
+error: Expected a JavaScript or TypeScript module, but identified a Css module. Importing these types of modules is currently not supported.
   Specifier: file:///[WILDLINE]/app.css
     at file:///[WILDLINE]/exists.ts:2:8
diff --git a/tests/specs/check/jsx_import_source_not_in_graph/__test__.jsonc b/tests/specs/check/jsx_import_source_not_in_graph/__test__.jsonc
new file mode 100644
index 0000000000..de0339cfb4
--- /dev/null
+++ b/tests/specs/check/jsx_import_source_not_in_graph/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "check main.ts",
+  "output": "main.out"
+}
diff --git a/tests/specs/check/jsx_import_source_not_in_graph/deno.json b/tests/specs/check/jsx_import_source_not_in_graph/deno.json
new file mode 100644
index 0000000000..219ef515f6
--- /dev/null
+++ b/tests/specs/check/jsx_import_source_not_in_graph/deno.json
@@ -0,0 +1,6 @@
+{
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "npm:preact"
+  }
+}
diff --git a/tests/specs/check/jsx_import_source_not_in_graph/main.out b/tests/specs/check/jsx_import_source_not_in_graph/main.out
new file mode 100644
index 0000000000..1830c3186d
--- /dev/null
+++ b/tests/specs/check/jsx_import_source_not_in_graph/main.out
@@ -0,0 +1 @@
+Check file:///[WILDLINE]/main.ts
diff --git a/tests/specs/check/jsx_import_source_not_in_graph/main.ts b/tests/specs/check/jsx_import_source_not_in_graph/main.ts
new file mode 100644
index 0000000000..bf6b817963
--- /dev/null
+++ b/tests/specs/check/jsx_import_source_not_in_graph/main.ts
@@ -0,0 +1 @@
+console.log("Hello");
diff --git a/tests/specs/check/package_json/install.out b/tests/specs/check/package_json/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/check/package_json/install.out
+++ b/tests/specs/check/package_json/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/check/package_json_auto_install/check.out b/tests/specs/check/package_json_auto_install/check.out
index db9bd198ca..6b75c8642d 100644
--- a/tests/specs/check/package_json_auto_install/check.out
+++ b/tests/specs/check/package_json_auto_install/check.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file://[WILDCARD]/main.ts
diff --git a/tests/specs/check/package_json_fail_check/install.out b/tests/specs/check/package_json_fail_check/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/check/package_json_fail_check/install.out
+++ b/tests/specs/check/package_json_fail_check/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/check/package_json_with_deno_json/install.out b/tests/specs/check/package_json_with_deno_json/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/check/package_json_with_deno_json/install.out
+++ b/tests/specs/check/package_json_with_deno_json/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/compile/byonm_main_sub_dir/deno.json b/tests/specs/compile/byonm_main_sub_dir/deno.json
index 6134d86d1c..fde86a1efb 100644
--- a/tests/specs/compile/byonm_main_sub_dir/deno.json
+++ b/tests/specs/compile/byonm_main_sub_dir/deno.json
@@ -1,3 +1,3 @@
 {
-  "unstable": ["byonm"]
+  "nodeModulesDir": "manual"
 }
diff --git a/tests/specs/compile/cjs/__test__.jsonc b/tests/specs/compile/cjs/__test__.jsonc
new file mode 100644
index 0000000000..9bdcf4724f
--- /dev/null
+++ b/tests/specs/compile/cjs/__test__.jsonc
@@ -0,0 +1,24 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "if": "unix",
+    "args": "compile --output main main.js",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "unix",
+    "commandName": "./main",
+    "args": [],
+    "output": "output.out",
+    "exitCode": 0
+  }, {
+    "if": "windows",
+    "args": "compile --output main.exe main.js",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "windows",
+    "commandName": "./main.exe",
+    "args": [],
+    "output": "output.out",
+    "exitCode": 0
+  }]
+}
diff --git a/tests/specs/compile/cjs/add.cjs b/tests/specs/compile/cjs/add.cjs
new file mode 100644
index 0000000000..bf90601267
--- /dev/null
+++ b/tests/specs/compile/cjs/add.cjs
@@ -0,0 +1 @@
+module.exports = (a, b) => a + b;
diff --git a/tests/specs/compile/cjs/divide.cts b/tests/specs/compile/cjs/divide.cts
new file mode 100644
index 0000000000..d89a600a4e
--- /dev/null
+++ b/tests/specs/compile/cjs/divide.cts
@@ -0,0 +1 @@
+module.exports.divide = (a: number, b: number) => a / b;
diff --git a/tests/specs/compile/cjs/main.js b/tests/specs/compile/cjs/main.js
new file mode 100644
index 0000000000..c2a8c7be02
--- /dev/null
+++ b/tests/specs/compile/cjs/main.js
@@ -0,0 +1,5 @@
+import { add } from "./reexport.cjs";
+import { multiply } from "./multiply.cts";
+
+console.log(add(1, 2));
+console.log(multiply(2, 3));
diff --git a/tests/specs/compile/cjs/multiply.cts b/tests/specs/compile/cjs/multiply.cts
new file mode 100644
index 0000000000..3c0618cfc5
--- /dev/null
+++ b/tests/specs/compile/cjs/multiply.cts
@@ -0,0 +1,4 @@
+/// <reference types="npm:@types/node" />
+exports.multiply = function (a: number, b: number): number {
+  return require("./divide.cts").divide(a, 1 / b);
+};
diff --git a/tests/specs/compile/cjs/output.out b/tests/specs/compile/cjs/output.out
new file mode 100644
index 0000000000..2559e5c49e
--- /dev/null
+++ b/tests/specs/compile/cjs/output.out
@@ -0,0 +1,2 @@
+3
+6
diff --git a/tests/specs/compile/cjs/reexport.cjs b/tests/specs/compile/cjs/reexport.cjs
new file mode 100644
index 0000000000..af7cecfdf4
--- /dev/null
+++ b/tests/specs/compile/cjs/reexport.cjs
@@ -0,0 +1 @@
+module.exports.add = require("./add.cjs");
diff --git a/tests/specs/compile/detect_cjs/__test__.jsonc b/tests/specs/compile/detect_cjs/__test__.jsonc
new file mode 100644
index 0000000000..0abf121f05
--- /dev/null
+++ b/tests/specs/compile/detect_cjs/__test__.jsonc
@@ -0,0 +1,27 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "args": "install",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "unix",
+    "args": "compile --output main main.js",
+    "output": "compile.out"
+  }, {
+    "if": "unix",
+    "commandName": "./main",
+    "args": [],
+    "output": "output.out",
+    "exitCode": 0
+  }, {
+    "if": "windows",
+    "args": "compile --output main.exe main.js",
+    "output": "compile.out"
+  }, {
+    "if": "windows",
+    "commandName": "./main.exe",
+    "args": [],
+    "output": "output.out",
+    "exitCode": 0
+  }]
+}
diff --git a/tests/specs/compile/detect_cjs/add.js b/tests/specs/compile/detect_cjs/add.js
new file mode 100644
index 0000000000..94b0263f0e
--- /dev/null
+++ b/tests/specs/compile/detect_cjs/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return require("./subtract.ts").subtract(a, -b);
+};
diff --git a/tests/specs/compile/detect_cjs/compile.out b/tests/specs/compile/detect_cjs/compile.out
new file mode 100644
index 0000000000..913e363c3e
--- /dev/null
+++ b/tests/specs/compile/detect_cjs/compile.out
@@ -0,0 +1,2 @@
+Check file:///[WILDLINE]/main.js
+Compile file:///[WILDLINE]
diff --git a/tests/specs/compile/detect_cjs/deno.json b/tests/specs/compile/detect_cjs/deno.json
new file mode 100644
index 0000000000..35f64c86f4
--- /dev/null
+++ b/tests/specs/compile/detect_cjs/deno.json
@@ -0,0 +1,5 @@
+{
+  "unstable": [
+    "detect-cjs"
+  ]
+}
diff --git a/tests/specs/compile/detect_cjs/main.js b/tests/specs/compile/detect_cjs/main.js
new file mode 100644
index 0000000000..8c55f673b0
--- /dev/null
+++ b/tests/specs/compile/detect_cjs/main.js
@@ -0,0 +1,3 @@
+import { add } from "./add.js";
+
+console.log(add(1, 2));
diff --git a/tests/specs/compile/detect_cjs/output.out b/tests/specs/compile/detect_cjs/output.out
new file mode 100644
index 0000000000..00750edc07
--- /dev/null
+++ b/tests/specs/compile/detect_cjs/output.out
@@ -0,0 +1 @@
+3
diff --git a/tests/specs/compile/detect_cjs/package.json b/tests/specs/compile/detect_cjs/package.json
new file mode 100644
index 0000000000..6e65b32ed5
--- /dev/null
+++ b/tests/specs/compile/detect_cjs/package.json
@@ -0,0 +1,6 @@
+{
+  "type": "commonjs",
+  "dependencies": {
+    "@types/node": "*"
+  }
+}
diff --git a/tests/specs/compile/detect_cjs/subtract.ts b/tests/specs/compile/detect_cjs/subtract.ts
new file mode 100644
index 0000000000..e4f6760b77
--- /dev/null
+++ b/tests/specs/compile/detect_cjs/subtract.ts
@@ -0,0 +1,2 @@
+/// <reference types="npm:@types/node" />
+module.exports.subtract = (a: number, b: number) => a - b;
diff --git a/tests/specs/compile/npmrc_byonm/install.out b/tests/specs/compile/npmrc_byonm/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/compile/npmrc_byonm/install.out
+++ b/tests/specs/compile/npmrc_byonm/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/compile/redirects/__test__.jsonc b/tests/specs/compile/redirects/__test__.jsonc
new file mode 100644
index 0000000000..07ce693999
--- /dev/null
+++ b/tests/specs/compile/redirects/__test__.jsonc
@@ -0,0 +1,22 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "if": "unix",
+    "args": "compile -A --output main main.ts",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "unix",
+    "commandName": "./main",
+    "args": [],
+    "output": "main.out"
+  }, {
+    "if": "windows",
+    "args": "compile -A --output main.exe main.ts",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "windows",
+    "commandName": "./main.exe",
+    "args": [],
+    "output": "main.out"
+  }]
+}
diff --git a/tests/specs/compile/redirects/main.out b/tests/specs/compile/redirects/main.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/compile/redirects/main.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/compile/redirects/main.ts b/tests/specs/compile/redirects/main.ts
new file mode 100644
index 0000000000..4396319014
--- /dev/null
+++ b/tests/specs/compile/redirects/main.ts
@@ -0,0 +1 @@
+import "http://localhost:4546/run/003_relative_import.ts";
diff --git a/tests/specs/future/unstable_flags/main.js b/tests/specs/future/unstable_flags/main.js
index 51af892f6b..8cc8960d97 100644
--- a/tests/specs/future/unstable_flags/main.js
+++ b/tests/specs/future/unstable_flags/main.js
@@ -1,4 +1,3 @@
-console.log(typeof await navigator.gpu.requestAdapter() === "object"); // Throws without `--unstable-gpu`
 console.log(typeof Deno.dlopen === "function"); // Undefined without `--unstable-ffi`
 console.log(
   // Undefined without `--unstable-fs`
diff --git a/tests/specs/future/unstable_flags/main.out b/tests/specs/future/unstable_flags/main.out
index b979d62f4f..bb101b641b 100644
--- a/tests/specs/future/unstable_flags/main.out
+++ b/tests/specs/future/unstable_flags/main.out
@@ -1,3 +1,2 @@
 true
 true
-true
diff --git a/tests/specs/info/import_map/__test__.jsonc b/tests/specs/info/import_map/__test__.jsonc
index 725276925e..7aba603e0b 100644
--- a/tests/specs/info/import_map/__test__.jsonc
+++ b/tests/specs/info/import_map/__test__.jsonc
@@ -1,5 +1,9 @@
 {
-  "args": "info preact/debug",
-  "output": "with_import_map.out",
-  "exitCode": 0
+  "steps": [
+    {
+      "args": "info preact/debug",
+      "output": "with_import_map.out",
+      "exitCode": 0
+    }
+  ]
 }
diff --git a/tests/specs/info/package_json_basic/install.out b/tests/specs/info/package_json_basic/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/info/package_json_basic/install.out
+++ b/tests/specs/info/package_json_basic/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/info/workspace_member/__test__.jsonc b/tests/specs/info/workspace_member/__test__.jsonc
new file mode 100644
index 0000000000..d13d3b03e8
--- /dev/null
+++ b/tests/specs/info/workspace_member/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tests": {
+    "member_folder": {
+      "args": "info --quiet foo",
+      "cwd": "member",
+      "output": "info_workspace_member.out",
+      "exitCode": 0
+    },
+    "member_folder_sub": {
+      "args": "info --quiet foo",
+      "cwd": "member/sub",
+      "output": "info_workspace_member_sub.out",
+      "exitCode": 0
+    }
+  }
+}
diff --git a/tests/specs/info/workspace_member/deno.json b/tests/specs/info/workspace_member/deno.json
new file mode 100644
index 0000000000..f88028aeab
--- /dev/null
+++ b/tests/specs/info/workspace_member/deno.json
@@ -0,0 +1,3 @@
+{
+  "workspace": ["./member"]
+}
diff --git a/tests/specs/info/workspace_member/info_workspace_member.out b/tests/specs/info/workspace_member/info_workspace_member.out
new file mode 100644
index 0000000000..e0dc0b6753
--- /dev/null
+++ b/tests/specs/info/workspace_member/info_workspace_member.out
@@ -0,0 +1,6 @@
+local: [WILDCARD]file.ts
+type: TypeScript
+dependencies: 0 unique
+size: [WILDCARD]
+
+file://[WILDCARD]/member/sub/file.ts ([WILDCARD])
diff --git a/tests/specs/info/workspace_member/info_workspace_member_sub.out b/tests/specs/info/workspace_member/info_workspace_member_sub.out
new file mode 100644
index 0000000000..e0dc0b6753
--- /dev/null
+++ b/tests/specs/info/workspace_member/info_workspace_member_sub.out
@@ -0,0 +1,6 @@
+local: [WILDCARD]file.ts
+type: TypeScript
+dependencies: 0 unique
+size: [WILDCARD]
+
+file://[WILDCARD]/member/sub/file.ts ([WILDCARD])
diff --git a/tests/specs/info/workspace_member/member/deno.json b/tests/specs/info/workspace_member/member/deno.json
new file mode 100644
index 0000000000..66aac29046
--- /dev/null
+++ b/tests/specs/info/workspace_member/member/deno.json
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "foo": "./sub/file.ts"
+  }
+}
diff --git a/tests/specs/info/workspace_member/member/sub/file.ts b/tests/specs/info/workspace_member/member/sub/file.ts
new file mode 100644
index 0000000000..cb0ff5c3b5
--- /dev/null
+++ b/tests/specs/info/workspace_member/member/sub/file.ts
@@ -0,0 +1 @@
+export {};
diff --git a/tests/specs/install/future_install_global/install.out b/tests/specs/install/future_install_global/install.out
index 58cd88ada1..0fa1b97191 100644
--- a/tests/specs/install/future_install_global/install.out
+++ b/tests/specs/install/future_install_global/install.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 ✅ Successfully installed deno-test-bin[WILDCARD]
 [WILDCARD]
diff --git a/tests/specs/install/future_install_local_add_deno/install.out b/tests/specs/install/future_install_local_add_deno/install.out
index 93894a020c..2f73e5afb5 100644
--- a/tests/specs/install/future_install_local_add_deno/install.out
+++ b/tests/specs/install/future_install_local_add_deno/install.out
@@ -1,3 +1,3 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/install/future_install_local_add_npm/install.out b/tests/specs/install/future_install_local_add_npm/install.out
index 42161f3ae1..44bd9cac7e 100644
--- a/tests/specs/install/future_install_local_add_npm/install.out
+++ b/tests/specs/install/future_install_local_add_npm/install.out
@@ -1,4 +1,4 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/future_install_local_add_npm/package.json.out b/tests/specs/install/future_install_local_add_npm/package.json.out
index ad8518e791..613d986360 100644
--- a/tests/specs/install/future_install_local_add_npm/package.json.out
+++ b/tests/specs/install/future_install_local_add_npm/package.json.out
@@ -1,3 +1,5 @@
 {
-  "dependencies": { "@denotest/esm-basic": "^1.0.0" }
+  "dependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  }
 }
diff --git a/tests/specs/install/future_install_local_deno/install.out b/tests/specs/install/future_install_local_deno/install.out
index 15263a37b5..d0972f69e8 100644
--- a/tests/specs/install/future_install_local_deno/install.out
+++ b/tests/specs/install/future_install_local_deno/install.out
@@ -8,7 +8,7 @@ Download http://localhost:4545/subdir/print_hello.ts
 Download http://127.0.0.1:4250/@denotest/add/meta.json
 Download http://127.0.0.1:4250/@denotest/add/1.0.0_meta.json
 Download http://127.0.0.1:4250/@denotest/add/1.0.0/mod.ts
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Download http://127.0.0.1:4250/@std/testing/1.0.0/bdd.ts
 Download http://127.0.0.1:4250/@std/testing/1.0.0/types.ts
diff --git a/tests/specs/install/future_install_node_modules/install.out b/tests/specs/install/future_install_node_modules/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/install/future_install_node_modules/install.out
+++ b/tests/specs/install/future_install_node_modules/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/import_map_with_dir/__test__.jsonc b/tests/specs/install/import_map_with_dir/__test__.jsonc
new file mode 100644
index 0000000000..cbbc7cc2e1
--- /dev/null
+++ b/tests/specs/install/import_map_with_dir/__test__.jsonc
@@ -0,0 +1,9 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install",
+      "output": ""
+    }
+  ]
+}
diff --git a/tests/specs/install/import_map_with_dir/deno.json b/tests/specs/install/import_map_with_dir/deno.json
new file mode 100644
index 0000000000..5c3224b071
--- /dev/null
+++ b/tests/specs/install/import_map_with_dir/deno.json
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@assets": "./src/assets/"
+  }
+}
diff --git a/tests/specs/install/install_add_dep_existing/__test__.jsonc b/tests/specs/install/install_add_dep_existing/__test__.jsonc
new file mode 100644
index 0000000000..74c509a57d
--- /dev/null
+++ b/tests/specs/install/install_add_dep_existing/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install npm:@denotest/esm-basic",
+      "output": "install.out"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('package.json').trim())"
+      ],
+      "output": "package.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/install/install_add_dep_existing/install.out b/tests/specs/install/install_add_dep_existing/install.out
new file mode 100644
index 0000000000..44bd9cac7e
--- /dev/null
+++ b/tests/specs/install/install_add_dep_existing/install.out
@@ -0,0 +1,4 @@
+Add npm:@denotest/esm-basic@1.0.0
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
+Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/install_add_dep_existing/package.json b/tests/specs/install/install_add_dep_existing/package.json
new file mode 100644
index 0000000000..d5ca56e004
--- /dev/null
+++ b/tests/specs/install/install_add_dep_existing/package.json
@@ -0,0 +1,3 @@
+{
+  "devDependencies": { "@denotest/esm-basic": "^1.0.0" }
+}
diff --git a/tests/specs/install/install_add_dep_existing/package.json.out b/tests/specs/install/install_add_dep_existing/package.json.out
new file mode 100644
index 0000000000..613d986360
--- /dev/null
+++ b/tests/specs/install/install_add_dep_existing/package.json.out
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  }
+}
diff --git a/tests/specs/install/install_add_dev/install.out b/tests/specs/install/install_add_dev/install.out
index 42161f3ae1..44bd9cac7e 100644
--- a/tests/specs/install/install_add_dev/install.out
+++ b/tests/specs/install/install_add_dev/install.out
@@ -1,4 +1,4 @@
 Add npm:@denotest/esm-basic@1.0.0
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/install_add_dev/package.json b/tests/specs/install/install_add_dev/package.json
index d5ca56e004..0967ef424b 100644
--- a/tests/specs/install/install_add_dev/package.json
+++ b/tests/specs/install/install_add_dev/package.json
@@ -1,3 +1 @@
-{
-  "devDependencies": { "@denotest/esm-basic": "^1.0.0" }
-}
+{}
diff --git a/tests/specs/install/install_add_dev/package.json.out b/tests/specs/install/install_add_dev/package.json.out
index d5ca56e004..866724397f 100644
--- a/tests/specs/install/install_add_dev/package.json.out
+++ b/tests/specs/install/install_add_dev/package.json.out
@@ -1,3 +1,5 @@
 {
-  "devDependencies": { "@denotest/esm-basic": "^1.0.0" }
+  "devDependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  }
 }
diff --git a/tests/specs/install/install_add_dev_existing/__test__.jsonc b/tests/specs/install/install_add_dev_existing/__test__.jsonc
new file mode 100644
index 0000000000..e4e2f8a31c
--- /dev/null
+++ b/tests/specs/install/install_add_dev_existing/__test__.jsonc
@@ -0,0 +1,16 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install --dev npm:@denotest/esm-basic",
+      "output": "install.out"
+    },
+    {
+      "args": [
+        "eval",
+        "console.log(Deno.readTextFileSync('package.json').trim())"
+      ],
+      "output": "package.json.out"
+    }
+  ]
+}
diff --git a/tests/specs/install/install_add_dev_existing/install.out b/tests/specs/install/install_add_dev_existing/install.out
new file mode 100644
index 0000000000..44bd9cac7e
--- /dev/null
+++ b/tests/specs/install/install_add_dev_existing/install.out
@@ -0,0 +1,4 @@
+Add npm:@denotest/esm-basic@1.0.0
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
+Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/install/install_add_dev_existing/package.json b/tests/specs/install/install_add_dev_existing/package.json
new file mode 100644
index 0000000000..ad8518e791
--- /dev/null
+++ b/tests/specs/install/install_add_dev_existing/package.json
@@ -0,0 +1,3 @@
+{
+  "dependencies": { "@denotest/esm-basic": "^1.0.0" }
+}
diff --git a/tests/specs/install/install_add_dev_existing/package.json.out b/tests/specs/install/install_add_dev_existing/package.json.out
new file mode 100644
index 0000000000..866724397f
--- /dev/null
+++ b/tests/specs/install/install_add_dev_existing/package.json.out
@@ -0,0 +1,5 @@
+{
+  "devDependencies": {
+    "@denotest/esm-basic": "^1.0.0"
+  }
+}
diff --git a/tests/specs/install/install_deprecated_package/install.out b/tests/specs/install/install_deprecated_package/install.out
index 95c0759092..32661d971d 100644
--- a/tests/specs/install/install_deprecated_package/install.out
+++ b/tests/specs/install/install_deprecated_package/install.out
@@ -1,5 +1,5 @@
 Add npm:@denotest/deprecated-package@1.0.0
-Download http://localhost:4260/@denotest/deprecated-package
+Download http://localhost:4260/@denotest%2fdeprecated-package
 Download http://localhost:4260/@denotest/deprecated-package/1.0.0.tgz
 Initialize @denotest/deprecated-package@1.0.0
 Warning The following packages are deprecated:
diff --git a/tests/specs/install/install_deprecated_package/package.json.out b/tests/specs/install/install_deprecated_package/package.json.out
index 4b4b08087a..0cf36cd24f 100644
--- a/tests/specs/install/install_deprecated_package/package.json.out
+++ b/tests/specs/install/install_deprecated_package/package.json.out
@@ -1,3 +1,5 @@
 {
-  "dependencies": { "@denotest/deprecated-package": "^1.0.0" }
+  "dependencies": {
+    "@denotest/deprecated-package": "^1.0.0"
+  }
 }
diff --git a/tests/specs/install/install_entrypoint/install.out b/tests/specs/install/install_entrypoint/install.out
index d702cf45ac..da10f3aa03 100644
--- a/tests/specs/install/install_entrypoint/install.out
+++ b/tests/specs/install/install_entrypoint/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
 Download http://127.0.0.1:4250/@denotest/add/meta.json
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://127.0.0.1:4250/@denotest/add/1.0.0_meta.json
 Download http://127.0.0.1:4250/@denotest/add/1.0.0/mod.ts
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/install/install_entrypoint/lifecycle.out b/tests/specs/install/install_entrypoint/lifecycle.out
index 8eae8ee120..b302ea3341 100644
--- a/tests/specs/install/install_entrypoint/lifecycle.out
+++ b/tests/specs/install/install_entrypoint/lifecycle.out
@@ -1,22 +1,11 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/node-lifecycle-scripts@1.0.0
 Initialize @denotest/bin@1.0.0
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'preinstall' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'install' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'postinstall' script
 [UNORDERED_END]
-preinstall
-deno preinstall.js
-node preinstall.js
-install
-hello from install script
-postinstall[WILDCARD]
- _____________
-< postinstall >
- -------------
-        \   ^__^
-         \  (oo)\_______
-            (__)\       )\/\
-                ||----w |
-                ||     ||
diff --git a/tests/specs/install/invalid_scheme/__test__.jsonc b/tests/specs/install/invalid_scheme/__test__.jsonc
new file mode 100644
index 0000000000..c4d3ebbf06
--- /dev/null
+++ b/tests/specs/install/invalid_scheme/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "tempDir": true,
+  "args": "install",
+  "output": "install.out"
+}
diff --git a/tests/specs/install/invalid_scheme/install.out b/tests/specs/install/invalid_scheme/install.out
new file mode 100644
index 0000000000..cf100216bd
--- /dev/null
+++ b/tests/specs/install/invalid_scheme/install.out
@@ -0,0 +1,5 @@
+Warning Not implemented scheme 'git'
+    at file:///[WILDLINE]/package.json
+Download http://localhost:4260/@denotest%2fadd
+Download http://localhost:4260/@denotest/add/1.0.0.tgz
+Initialize @denotest/add@1.0.0
diff --git a/tests/specs/install/invalid_scheme/package.json b/tests/specs/install/invalid_scheme/package.json
new file mode 100644
index 0000000000..5e50ae591d
--- /dev/null
+++ b/tests/specs/install/invalid_scheme/package.json
@@ -0,0 +1,6 @@
+{
+  "dependencies": {
+    "@denotest/add": "*",
+    "deno": "git:denoland/deno"
+  }
+}
diff --git a/tests/specs/install/jsr_exports/__test__.jsonc b/tests/specs/install/jsr_exports/__test__.jsonc
new file mode 100644
index 0000000000..7ccc5da4d9
--- /dev/null
+++ b/tests/specs/install/jsr_exports/__test__.jsonc
@@ -0,0 +1,7 @@
+{
+  "tempDir": true,
+  "steps": [
+    { "args": "install", "output": "install.out" },
+    { "args": "run --cached-only main.ts", "output": "main.out" }
+  ]
+}
diff --git a/tests/specs/install/jsr_exports/deno.json b/tests/specs/install/jsr_exports/deno.json
new file mode 100644
index 0000000000..4b281f80ae
--- /dev/null
+++ b/tests/specs/install/jsr_exports/deno.json
@@ -0,0 +1,5 @@
+{
+  "imports": {
+    "@denotest/multiple-exports": "jsr:@denotest/multiple-exports@^1.0.0"
+  }
+}
diff --git a/tests/specs/install/jsr_exports/install.out b/tests/specs/install/jsr_exports/install.out
new file mode 100644
index 0000000000..bce0d79bb3
--- /dev/null
+++ b/tests/specs/install/jsr_exports/install.out
@@ -0,0 +1,13 @@
+[UNORDERED_START]
+Download http://127.0.0.1:4250/@denotest/multiple-exports/meta.json
+Download http://127.0.0.1:4250/@denotest/multiple-exports/1.0.0_meta.json
+Download http://127.0.0.1:4250/@denotest/multiple-exports/1.0.0/add.ts
+Download http://127.0.0.1:4250/@denotest/multiple-exports/1.0.0/subtract.ts
+Download http://127.0.0.1:4250/@denotest/multiple-exports/1.0.0/data.json
+Download http://127.0.0.1:4250/@denotest/add/meta.json
+Download http://127.0.0.1:4250/@denotest/subtract/meta.json
+Download http://127.0.0.1:4250/@denotest/add/1.0.0_meta.json
+Download http://127.0.0.1:4250/@denotest/subtract/1.0.0_meta.json
+Download http://127.0.0.1:4250/@denotest/add/1.0.0/mod.ts
+Download http://127.0.0.1:4250/@denotest/subtract/1.0.0/mod.ts
+[UNORDERED_END]
diff --git a/tests/specs/install/jsr_exports/main.out b/tests/specs/install/jsr_exports/main.out
new file mode 100644
index 0000000000..6ce184bada
--- /dev/null
+++ b/tests/specs/install/jsr_exports/main.out
@@ -0,0 +1,3 @@
+3
+-1
+{ a: 1 }
diff --git a/tests/specs/install/jsr_exports/main.ts b/tests/specs/install/jsr_exports/main.ts
new file mode 100644
index 0000000000..f7efdb0e98
--- /dev/null
+++ b/tests/specs/install/jsr_exports/main.ts
@@ -0,0 +1,7 @@
+import { add } from "@denotest/multiple-exports/add";
+import { subtract } from "@denotest/multiple-exports/subtract";
+import data from "@denotest/multiple-exports/data-json" with { type: "json" };
+
+console.log(add(1, 2));
+console.log(subtract(1, 2));
+console.log(data);
diff --git a/tests/specs/install/non_existent_optional_peer/install.out b/tests/specs/install/non_existent_optional_peer/install.out
index 292c1a4e2f..694d4b51b8 100644
--- a/tests/specs/install/non_existent_optional_peer/install.out
+++ b/tests/specs/install/non_existent_optional_peer/install.out
@@ -1,5 +1,5 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/non-existent-optional-peer
+Download http://localhost:4260/@denotest%2fnon-existent-optional-peer
 Download http://localhost:4260/uWebSockets.js
 Download http://localhost:4260/@denotest/non-existent-optional-peer/1.0.0.tgz
 [UNORDERED_END]
diff --git a/tests/specs/install/type_only_import/__test__.jsonc b/tests/specs/install/type_only_import/__test__.jsonc
new file mode 100644
index 0000000000..22b8134ac3
--- /dev/null
+++ b/tests/specs/install/type_only_import/__test__.jsonc
@@ -0,0 +1,10 @@
+{
+  "tempDir": true,
+  "steps": [
+    { "args": "install -e main.ts", "output": "install.out" },
+    {
+      "args": "run --check --cached-only main.ts",
+      "output": "run.out"
+    }
+  ]
+}
diff --git a/tests/specs/install/type_only_import/install.out b/tests/specs/install/type_only_import/install.out
new file mode 100644
index 0000000000..1bdbec4e58
--- /dev/null
+++ b/tests/specs/install/type_only_import/install.out
@@ -0,0 +1,6 @@
+Download http://127.0.0.1:4250/@denotest/type-only-import/meta.json
+Download http://127.0.0.1:4250/@denotest/type-only-import/1.0.0_meta.json
+[UNORDERED_START]
+Download http://127.0.0.1:4250/@denotest/type-only-import/1.0.0/mod.ts
+Download http://127.0.0.1:4250/@denotest/type-only-import/1.0.0/foo.ts
+[UNORDERED_END]
diff --git a/tests/specs/install/type_only_import/main.ts b/tests/specs/install/type_only_import/main.ts
new file mode 100644
index 0000000000..bf22935a2d
--- /dev/null
+++ b/tests/specs/install/type_only_import/main.ts
@@ -0,0 +1,3 @@
+import { foo } from "jsr:@denotest/type-only-import";
+
+console.log(foo.bar);
diff --git a/tests/specs/install/type_only_import/run.out b/tests/specs/install/type_only_import/run.out
new file mode 100644
index 0000000000..d36ac8aa37
--- /dev/null
+++ b/tests/specs/install/type_only_import/run.out
@@ -0,0 +1,2 @@
+Check [WILDCARD]main.ts
+foo
diff --git a/tests/specs/install/workspace_member_with_tag_dep/install.out b/tests/specs/install/workspace_member_with_tag_dep/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/install/workspace_member_with_tag_dep/install.out
+++ b/tests/specs/install/workspace_member_with_tag_dep/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/lint/node_globals_no_duplicate_imports/main.out b/tests/specs/lint/node_globals_no_duplicate_imports/main.out
index 56df10eba4..058b80795d 100644
--- a/tests/specs/lint/node_globals_no_duplicate_imports/main.out
+++ b/tests/specs/lint/node_globals_no_duplicate_imports/main.out
@@ -2,3 +2,6 @@ error: Uncaught (in promise) ReferenceError: setImmediate is not defined
 const _foo = setImmediate;
              ^
     at [WILDCARD]main.ts:3:14
+
+    info: setImmediate is not available in the global scope in Deno.
+    hint: Import it explicitly with import { setImmediate } from "node:timers";.
diff --git a/tests/specs/lockfile/frozen_lockfile/__test__.jsonc b/tests/specs/lockfile/frozen_lockfile/__test__.jsonc
index 7a7b9c233a..07ec2c4c14 100644
--- a/tests/specs/lockfile/frozen_lockfile/__test__.jsonc
+++ b/tests/specs/lockfile/frozen_lockfile/__test__.jsonc
@@ -183,6 +183,19 @@
           "exitCode": 1
         }
       ]
+    },
+    "check_subcommand": {
+      "steps": [
+        {
+          "args": "check --frozen=true add.ts",
+          "output": "[WILDCARD]The lockfile is out of date[WILDCARD]",
+          "exitCode": 1
+        },
+        {
+          "args": "check --frozen=false add.ts",
+          "output": "[WILDCARD]Check [WILDCARD]add.ts\n"
+        }
+      ]
     }
   }
 }
diff --git a/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_dynamic_npm.out b/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_dynamic_npm.out
index 4ae4d059cc..4fc016c57c 100644
--- a/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_dynamic_npm.out
+++ b/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_dynamic_npm.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/subtract
+Download http://localhost:4260/@denotest%2fsubtract
 error: Uncaught (in promise) TypeError: The lockfile is out of date. Run `deno install --frozen=false`, or rerun with `--frozen=false` to update it.
 changes:
  4 | -    "npm:@denotest/add@1": "1.0.0"
diff --git a/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_run.out b/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_run.out
index 057b9632b3..07b37b925a 100644
--- a/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_run.out
+++ b/tests/specs/lockfile/frozen_lockfile/frozen_new_dep_run.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/subtract
+Download http://localhost:4260/@denotest%2fsubtract
 error: The lockfile is out of date. Run `deno install --frozen=false`, or rerun with `--frozen=false` to update it.
 changes:
  4 | -    "npm:@denotest/add@1": "1.0.0"
diff --git a/tests/specs/lockfile/frozen_lockfile/frozen_package_json_changed.out b/tests/specs/lockfile/frozen_lockfile/frozen_package_json_changed.out
index dc31a1a653..626007478f 100644
--- a/tests/specs/lockfile/frozen_lockfile/frozen_package_json_changed.out
+++ b/tests/specs/lockfile/frozen_lockfile/frozen_package_json_changed.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 error: The lockfile is out of date. Run `deno install --frozen=false`, or rerun with `--frozen=false` to update it.
 changes:
  4 | -    "npm:@denotest/add@1": "1.0.0"
diff --git a/tests/specs/lockfile/frozen_lockfile/no_lockfile_run.out b/tests/specs/lockfile/frozen_lockfile/no_lockfile_run.out
index 27dc66fd2f..047bfdb4ac 100644
--- a/tests/specs/lockfile/frozen_lockfile/no_lockfile_run.out
+++ b/tests/specs/lockfile/frozen_lockfile/no_lockfile_run.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/add
+Download http://localhost:4260/@denotest%2fadd
 error: The lockfile is out of date. Run `deno install --frozen=false`, or rerun with `--frozen=false` to update it.
 changes:
  1 | -
diff --git a/tests/specs/lockfile/only_package_json/install.out b/tests/specs/lockfile/only_package_json/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/lockfile/only_package_json/install.out
+++ b/tests/specs/lockfile/only_package_json/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/node/child_process_extra_pipes/main.out b/tests/specs/node/child_process_extra_pipes/main.out
index 694126b924..436afd2f75 100644
--- a/tests/specs/node/child_process_extra_pipes/main.out
+++ b/tests/specs/node/child_process_extra_pipes/main.out
@@ -1,5 +1,5 @@
-data: hello world
 [UNORDERED_START]
 child closed
+got: hello world
 pipe closed
 [UNORDERED_END]
diff --git a/tests/specs/node/child_process_extra_pipes/main.ts b/tests/specs/node/child_process_extra_pipes/main.ts
index a3683fe9ee..2837cdc53c 100644
--- a/tests/specs/node/child_process_extra_pipes/main.ts
+++ b/tests/specs/node/child_process_extra_pipes/main.ts
@@ -1,5 +1,4 @@
 import child_process from "node:child_process";
-import { Buffer } from "node:buffer";
 import console from "node:console";
 
 const child = child_process.spawn("./test-pipe/target/debug/test-pipe", [], {
@@ -8,19 +7,32 @@ const child = child_process.spawn("./test-pipe/target/debug/test-pipe", [], {
 
 const extra = child.stdio[4];
 
-const p = Promise.withResolvers();
+if (!extra) {
+  throw new Error("no extra pipe");
+}
+
+const p = Promise.withResolvers<void>();
+
+let got = "";
 
 child.on("close", () => {
   console.log("child closed");
-  p.resolve();
+  console.log("got:", got);
+  if (got === "hello world") {
+    p.resolve();
+  } else {
+    p.reject(new Error(`wanted "hello world", got "${got}"`));
+  }
 });
 
 extra.on("data", (d) => {
-  console.log("data:", d.toString().trim());
+  got += d.toString();
 });
 
 extra.on("close", () => {
   console.log("pipe closed");
 });
 
+extra.write("start");
+
 await p.promise;
diff --git a/tests/specs/node/child_process_extra_pipes/test-pipe/src/main.rs b/tests/specs/node/child_process_extra_pipes/test-pipe/src/main.rs
index 192f827313..acc034830f 100644
--- a/tests/specs/node/child_process_extra_pipes/test-pipe/src/main.rs
+++ b/tests/specs/node/child_process_extra_pipes/test-pipe/src/main.rs
@@ -1,12 +1,31 @@
+use std::fs::File;
 use std::io::prelude::*;
 use std::os::fd::FromRawFd;
-use std::os::unix::net::UnixStream;
 
 fn main() {
   #[cfg(unix)]
   {
-    let mut stream = unsafe { UnixStream::from_raw_fd(4) };
+    let mut pipe = unsafe { File::from_raw_fd(4) };
 
-    stream.write_all(b"hello world\n").unwrap();
+    let mut read = 0;
+    let mut buf = [0u8; 1024];
+    loop {
+      if read > 4 {
+        assert_eq!(&buf[..5], b"start");
+        break;
+      }
+      match pipe.read(&mut buf) {
+        Ok(n) => {
+          read += n;
+        }
+        Ok(0) => {
+          return;
+        }
+        Err(e) => {
+          eprintln!("GOT ERROR: {e:?}");
+        }
+      }
+    }
+    pipe.write_all(b"hello world").unwrap();
   }
 }
diff --git a/tests/specs/node/cjs_reexport_same_specifier_in_sub_folder/main.out b/tests/specs/node/cjs_reexport_same_specifier_in_sub_folder/main.out
index 321d995b8a..c50f064d7f 100644
--- a/tests/specs/node/cjs_reexport_same_specifier_in_sub_folder/main.out
+++ b/tests/specs/node/cjs_reexport_same_specifier_in_sub_folder/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/cjs-reexport-same-specifier-in-sub-folder
+Download http://localhost:4260/@denotest%2fcjs-reexport-same-specifier-in-sub-folder
 Download http://localhost:4260/@denotest/cjs-reexport-same-specifier-in-sub-folder/1.0.0.tgz
 [Module: null prototype] {
   default: { main: [Getter], sub: [Getter] },
diff --git a/tests/specs/node/next_tick_uncaught_exception/__test__.jsonc b/tests/specs/node/next_tick_uncaught_exception/__test__.jsonc
new file mode 100644
index 0000000000..5517e693d6
--- /dev/null
+++ b/tests/specs/node/next_tick_uncaught_exception/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run main.ts",
+  "output": "main.out"
+}
diff --git a/tests/specs/node/next_tick_uncaught_exception/main.out b/tests/specs/node/next_tick_uncaught_exception/main.out
new file mode 100644
index 0000000000..45b756515b
--- /dev/null
+++ b/tests/specs/node/next_tick_uncaught_exception/main.out
@@ -0,0 +1,2 @@
+caught Error: thrown from next tick
+    at file:///[WILDCARD]/specs/node/next_tick_uncaught_exception/main.ts:4:15
diff --git a/tests/specs/node/next_tick_uncaught_exception/main.ts b/tests/specs/node/next_tick_uncaught_exception/main.ts
new file mode 100644
index 0000000000..2679d3d54b
--- /dev/null
+++ b/tests/specs/node/next_tick_uncaught_exception/main.ts
@@ -0,0 +1,13 @@
+import process from "node:process";
+import { strictEqual } from "node:assert";
+
+const error = new Error("thrown from next tick");
+
+process.on("uncaughtException", (caught) => {
+  strictEqual(caught, error);
+  console.log("caught", caught);
+});
+
+process.nextTick(() => {
+  throw error;
+});
diff --git a/tests/specs/node/require_export_from_parent_with_no_filename/__test__.jsonc b/tests/specs/node/require_export_from_parent_with_no_filename/__test__.jsonc
new file mode 100644
index 0000000000..a3de08e460
--- /dev/null
+++ b/tests/specs/node/require_export_from_parent_with_no_filename/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tempDir": true,
+  "steps": [
+    {
+      "args": "install",
+      "output": "[WILDCARD]"
+    },
+    {
+      "args": "run -A main.cjs",
+      "output": "3\n"
+    }
+  ]
+}
diff --git a/tests/specs/node/require_export_from_parent_with_no_filename/main.cjs b/tests/specs/node/require_export_from_parent_with_no_filename/main.cjs
new file mode 100644
index 0000000000..3335ae1bf9
--- /dev/null
+++ b/tests/specs/node/require_export_from_parent_with_no_filename/main.cjs
@@ -0,0 +1,16 @@
+const path = require("node:path");
+const Module = require("node:module");
+function requireFromString(code, filename) {
+  const paths = Module._nodeModulePaths((0, path.dirname)(filename));
+  const m = new Module(filename, module.parent);
+  m.paths = paths;
+  m._compile(code, filename);
+  return m.exports;
+}
+
+const code = `
+const add = require("@denotest/cjs-multiple-exports/add");
+
+console.log(add(1, 2));
+`;
+requireFromString(code, "fake.js");
diff --git a/tests/specs/node/require_export_from_parent_with_no_filename/package.json b/tests/specs/node/require_export_from_parent_with_no_filename/package.json
new file mode 100644
index 0000000000..9cd6438953
--- /dev/null
+++ b/tests/specs/node/require_export_from_parent_with_no_filename/package.json
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "@denotest/cjs-multiple-exports": "1.0.0"
+  }
+}
diff --git a/tests/specs/npm/adding_npm_dep_in_dynamic_import/main.out b/tests/specs/npm/adding_npm_dep_in_dynamic_import/main.out
index fe612aa3c1..44c76f28d1 100644
--- a/tests/specs/npm/adding_npm_dep_in_dynamic_import/main.out
+++ b/tests/specs/npm/adding_npm_dep_in_dynamic_import/main.out
@@ -1,8 +1,8 @@
-Download http://localhost:4260/@denotest/add
+Download http://localhost:4260/@denotest%2fadd
 Download http://localhost:4260/@denotest/add/1.0.0.tgz
 Initialize @denotest/add@1.0.0
 3
-Download http://localhost:4260/@denotest/subtract
+Download http://localhost:4260/@denotest%2fsubtract
 Download http://localhost:4260/@denotest/subtract/1.0.0.tgz
 Initialize @denotest/subtract@1.0.0
 1
diff --git a/tests/specs/npm/bin_entries_prefer_closer/install.out b/tests/specs/npm/bin_entries_prefer_closer/install.out
index 1d3a995b80..1c9472f46f 100644
--- a/tests/specs/npm/bin_entries_prefer_closer/install.out
+++ b/tests/specs/npm/bin_entries_prefer_closer/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/transitive-bin
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2ftransitive-bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Download http://localhost:4260/@denotest/transitive-bin/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/0.7.0.tgz
diff --git a/tests/specs/npm/check_all/check_errors/main_all.out b/tests/specs/npm/check_all/check_errors/main_all.out
index 4c624c0eaa..c7797e43d2 100644
--- a/tests/specs/npm/check_all/check_errors/main_all.out
+++ b/tests/specs/npm/check_all/check_errors/main_all.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/check-error
+Download http://localhost:4260/@denotest%2fcheck-error
 Download http://localhost:4260/@denotest/check-error/1.0.0.tgz
 Check file:///[WILDCARD]/check_errors/main.ts
 error: TS2506 [ERROR]: 'Class1' is referenced directly or indirectly in its own base expression.
diff --git a/tests/specs/npm/check_all/check_errors/main_local.out b/tests/specs/npm/check_all/check_errors/main_local.out
index 4d3a892e74..ac58a29c76 100644
--- a/tests/specs/npm/check_all/check_errors/main_local.out
+++ b/tests/specs/npm/check_all/check_errors/main_local.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/check-error
+Download http://localhost:4260/@denotest%2fcheck-error
 Download http://localhost:4260/@denotest/check-error/1.0.0.tgz
 Check file:///[WILDCARD]/check_errors/main.ts
 error: TS2339 [ERROR]: Property 'Asdf' does not exist on type 'typeof import("file:///[WILDCARD]/@denotest/check-error/1.0.0/index.d.ts")'.
diff --git a/tests/specs/npm/check_local/check_errors/main_all.out b/tests/specs/npm/check_local/check_errors/main_all.out
index 4c624c0eaa..c7797e43d2 100644
--- a/tests/specs/npm/check_local/check_errors/main_all.out
+++ b/tests/specs/npm/check_local/check_errors/main_all.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/check-error
+Download http://localhost:4260/@denotest%2fcheck-error
 Download http://localhost:4260/@denotest/check-error/1.0.0.tgz
 Check file:///[WILDCARD]/check_errors/main.ts
 error: TS2506 [ERROR]: 'Class1' is referenced directly or indirectly in its own base expression.
diff --git a/tests/specs/npm/check_local/check_errors/main_local.out b/tests/specs/npm/check_local/check_errors/main_local.out
index 1a150b5e69..1eb8eef9fe 100644
--- a/tests/specs/npm/check_local/check_errors/main_local.out
+++ b/tests/specs/npm/check_local/check_errors/main_local.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/check-error
+Download http://localhost:4260/@denotest%2fcheck-error
 Download http://localhost:4260/@denotest/check-error/1.0.0.tgz
 Check file:///[WILDCARD]/check_errors/main.ts
 error: TS2339 [ERROR]: Property 'Asdf' does not exist on type 'typeof import("file:///[WILDCARD]/@denotest/check-error/1.0.0/index.d.ts")'.
diff --git a/tests/specs/npm/check_package_file_dts_dmts_dcts/file_dts_dmts_dcts/main.out b/tests/specs/npm/check_package_file_dts_dmts_dcts/file_dts_dmts_dcts/main.out
index 507d2c2f79..6ab72f53b7 100644
--- a/tests/specs/npm/check_package_file_dts_dmts_dcts/file_dts_dmts_dcts/main.out
+++ b/tests/specs/npm/check_package_file_dts_dmts_dcts/file_dts_dmts_dcts/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/file-dts-dmts-dcts
+Download http://localhost:4260/@denotest%2ffile-dts-dmts-dcts
 Download http://localhost:4260/@denotest/file-dts-dmts-dcts/1.0.0.tgz
 Check file:///[WILDCARD]/main.ts
 error: TS2322 [ERROR]: Type '5' is not assignable to type '"dts"'.
diff --git a/tests/specs/npm/check_pkg_json_import/main.out b/tests/specs/npm/check_pkg_json_import/main.out
index b60509c9a7..11f94272a5 100644
--- a/tests/specs/npm/check_pkg_json_import/main.out
+++ b/tests/specs/npm/check_pkg_json_import/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/types-pkg-json-import
+Download http://localhost:4260/@denotest%2ftypes-pkg-json-import
 Download http://localhost:4260/@denotest/types-pkg-json-import/1.0.0.tgz
 Check file:///[WILDLINE]/main.ts
diff --git a/tests/specs/npm/cjs_import_dual/check.out b/tests/specs/npm/cjs_import_dual/check.out
index be1fe86a69..c2d1daa17b 100644
--- a/tests/specs/npm/cjs_import_dual/check.out
+++ b/tests/specs/npm/cjs_import_dual/check.out
@@ -1,5 +1,5 @@
-Download http://localhost:4260/@denotest/cjs-import-dual
-Download http://localhost:4260/@denotest/dual-cjs-esm
+Download http://localhost:4260/@denotest%2fcjs-import-dual
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
 Download http://localhost:4260/@denotest/cjs-import-dual/1.0.0.tgz
 Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
 Check file:///[WILDLINE]/cjs_import_dual/main.ts
diff --git a/tests/specs/npm/cjs_import_dual/run.out b/tests/specs/npm/cjs_import_dual/run.out
index 2c05e125e1..0307bf2503 100644
--- a/tests/specs/npm/cjs_import_dual/run.out
+++ b/tests/specs/npm/cjs_import_dual/run.out
@@ -1,5 +1,5 @@
-Download http://localhost:4260/@denotest/cjs-import-dual
-Download http://localhost:4260/@denotest/dual-cjs-esm
+Download http://localhost:4260/@denotest%2fcjs-import-dual
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
 Download http://localhost:4260/@denotest/cjs-import-dual/1.0.0.tgz
 Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
 cjs
diff --git a/tests/specs/npm/cjs_local_global_decls/cjs_local_global_decls/main.out b/tests/specs/npm/cjs_local_global_decls/cjs_local_global_decls/main.out
index 5e7a36c8d0..5c48b5b5cf 100644
--- a/tests/specs/npm/cjs_local_global_decls/cjs_local_global_decls/main.out
+++ b/tests/specs/npm/cjs_local_global_decls/cjs_local_global_decls/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/cjs-local-global-decls
+Download http://localhost:4260/@denotest%2fcjs-local-global-decls
 Download http://localhost:4260/@denotest/cjs-local-global-decls/1.0.0.tgz
 Loaded.
diff --git a/tests/specs/npm/cjs_pkg_imports/cjs_pkg_imports/main.out b/tests/specs/npm/cjs_pkg_imports/cjs_pkg_imports/main.out
index 661146bd03..f9390fb1bc 100644
--- a/tests/specs/npm/cjs_pkg_imports/cjs_pkg_imports/main.out
+++ b/tests/specs/npm/cjs_pkg_imports/cjs_pkg_imports/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/cjs-pkg-imports
+Download http://localhost:4260/@denotest%2fcjs-pkg-imports
 Download http://localhost:4260/@denotest/cjs-pkg-imports/1.0.0.tgz
 { crypto: Crypto { subtle: SubtleCrypto {} }, number: 5 }
diff --git a/tests/specs/npm/compare_globals/__test__.jsonc b/tests/specs/npm/compare_globals/__test__.jsonc
index e096ddeb22..96458306a7 100644
--- a/tests/specs/npm/compare_globals/__test__.jsonc
+++ b/tests/specs/npm/compare_globals/__test__.jsonc
@@ -1,4 +1,4 @@
 {
-  "args": "run --allow-read --check=all compare_globals/main.ts",
-  "output": "compare_globals/main.out"
+  "args": "run --allow-read --check=all main.ts",
+  "output": "main.out"
 }
diff --git a/tests/specs/npm/compare_globals/compare_globals/main.out b/tests/specs/npm/compare_globals/main.out
similarity index 76%
rename from tests/specs/npm/compare_globals/compare_globals/main.out
rename to tests/specs/npm/compare_globals/main.out
index a1b0a566d5..290e9c3b23 100644
--- a/tests/specs/npm/compare_globals/compare_globals/main.out
+++ b/tests/specs/npm/compare_globals/main.out
@@ -1,17 +1,18 @@
 [UNORDERED_START]
-Download http://localhost:4260/@types/node
+Download http://localhost:4260/@types%2fnode
 Download http://localhost:4260/undici-types
-Download http://localhost:4260/@denotest/globals
+Download http://localhost:4260/@denotest%2fglobals
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/globals/1.0.0.tgz
 Download http://localhost:4260/@types/node/node-22.5.4.tgz
 Download http://localhost:4260/undici-types/undici-types-6.19.8.tgz
 [UNORDERED_END]
-Check file:///[WILDCARD]/compare_globals/main.ts
+Check file:///[WILDCARD]/main.ts
 true
 true
 []
+process equals process true
 setTimeout 1 false
 setTimeout 2 function
 setTimeout 3 function
diff --git a/tests/specs/npm/compare_globals/compare_globals/main.ts b/tests/specs/npm/compare_globals/main.ts
similarity index 84%
rename from tests/specs/npm/compare_globals/compare_globals/main.ts
rename to tests/specs/npm/compare_globals/main.ts
index 9482798d8c..308ce9b23f 100644
--- a/tests/specs/npm/compare_globals/compare_globals/main.ts
+++ b/tests/specs/npm/compare_globals/main.ts
@@ -5,10 +5,17 @@ console.log(globals.global === globals.globalThis);
 // @ts-expect-error even though these are the same object, they have different types
 console.log(globals.globalThis === globalThis);
 console.log(globals.process.execArgv);
+console.log("process equals process", process === globals.process);
 
 type AssertTrue<T extends true> = never;
-type _TestNoProcessGlobal = AssertTrue<
-  typeof globalThis extends { process: any } ? false : true
+type _TestHasProcessGlobal = AssertTrue<
+  typeof globalThis extends { process: any } ? true : false
+>;
+type _TestProcessGlobalVersion = AssertTrue<
+  typeof process.versions.node extends string ? true : false
+>;
+type _TestNoBufferGlogal = AssertTrue<
+  typeof globalThis extends { Buffer: any } ? false : true
 >;
 type _TestHasNodeJsGlobal = NodeJS.Architecture;
 
diff --git a/tests/specs/npm/conditional_exports/main.out b/tests/specs/npm/conditional_exports/main.out
index 8bd31321b6..8b5b2715be 100644
--- a/tests/specs/npm/conditional_exports/main.out
+++ b/tests/specs/npm/conditional_exports/main.out
@@ -1,8 +1,8 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/conditional-exports
+Download http://localhost:4260/@denotest%2fconditional-exports
 Download http://localhost:4260/supports-esm
 Download http://localhost:4260/has-package-exports
-Download http://localhost:4260/@ljharb/has-package-exports-patterns
+Download http://localhost:4260/@ljharb%2fhas-package-exports-patterns
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/conditional-exports/1.0.0.tgz
diff --git a/tests/specs/npm/conditional_exports_node_modules_dir/main.out b/tests/specs/npm/conditional_exports_node_modules_dir/main.out
index 5fbba560d3..ee4a64be61 100644
--- a/tests/specs/npm/conditional_exports_node_modules_dir/main.out
+++ b/tests/specs/npm/conditional_exports_node_modules_dir/main.out
@@ -1,8 +1,8 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/conditional-exports
+Download http://localhost:4260/@denotest%2fconditional-exports
 Download http://localhost:4260/supports-esm
 Download http://localhost:4260/has-package-exports
-Download http://localhost:4260/@ljharb/has-package-exports-patterns
+Download http://localhost:4260/@ljharb%2fhas-package-exports-patterns
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/conditional-exports/1.0.0.tgz
diff --git a/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_index_js.out b/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_index_js.out
index a700b8fdb6..c1eb2a4801 100644
--- a/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_index_js.out
+++ b/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_index_js.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/sub-folders
+Download http://localhost:4260/@denotest%2fsub-folders
 Download http://localhost:4260/@denotest/sub-folders/1.0.0.tgz
 error: Directory import [WILDCARD]folder_index_js is not supported resolving import from file:///[WILDCARD]/directory_import/folder_index_js.ts
 Did you mean to import index.js within the directory?
diff --git a/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_no_index.out b/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_no_index.out
index 844419b4c6..c19c4bcaa4 100644
--- a/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_no_index.out
+++ b/tests/specs/npm/directory_import_folder_index_js/directory_import/folder_no_index.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/sub-folders
+Download http://localhost:4260/@denotest%2fsub-folders
 Download http://localhost:4260/@denotest/sub-folders/1.0.0.tgz
 error: Directory import [WILDCARD]folder_no_index is not supported resolving import from file:///[WILDCARD]/folder_no_index.ts
 
diff --git a/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_index_js.out b/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_index_js.out
index a700b8fdb6..c1eb2a4801 100644
--- a/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_index_js.out
+++ b/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_index_js.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/sub-folders
+Download http://localhost:4260/@denotest%2fsub-folders
 Download http://localhost:4260/@denotest/sub-folders/1.0.0.tgz
 error: Directory import [WILDCARD]folder_index_js is not supported resolving import from file:///[WILDCARD]/directory_import/folder_index_js.ts
 Did you mean to import index.js within the directory?
diff --git a/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_no_index.out b/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_no_index.out
index 844419b4c6..c19c4bcaa4 100644
--- a/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_no_index.out
+++ b/tests/specs/npm/directory_import_folder_no_index/directory_import/folder_no_index.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/sub-folders
+Download http://localhost:4260/@denotest%2fsub-folders
 Download http://localhost:4260/@denotest/sub-folders/1.0.0.tgz
 error: Directory import [WILDCARD]folder_no_index is not supported resolving import from file:///[WILDCARD]/folder_no_index.ts
 
diff --git a/tests/specs/npm/dynamic_npm_resolution_failure/main.out b/tests/specs/npm/dynamic_npm_resolution_failure/main.out
index d9eb7182fa..8888c4f0ae 100644
--- a/tests/specs/npm/dynamic_npm_resolution_failure/main.out
+++ b/tests/specs/npm/dynamic_npm_resolution_failure/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
 Download http://localhost:4260/chalk
-Download http://localhost:4260/@denotest/dep-cannot-parse
+Download http://localhost:4260/@denotest%2fdep-cannot-parse
 [UNORDERED_END]
 Download http://localhost:4260/chalk/chalk-5.0.1.tgz
 Hi
diff --git a/tests/specs/npm/esm_import_cjs_default/main.out b/tests/specs/npm/esm_import_cjs_default/main.out
index ec7962e5a3..6528a68d7c 100644
--- a/tests/specs/npm/esm_import_cjs_default/main.out
+++ b/tests/specs/npm/esm_import_cjs_default/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/esm-import-cjs-default
-Download http://localhost:4260/@denotest/cjs-default-export
+Download http://localhost:4260/@denotest%2fesm-import-cjs-default
+Download http://localhost:4260/@denotest%2fcjs-default-export
 Download http://localhost:4260/@denotest/cjs-default-export/1.0.0.tgz
 Download http://localhost:4260/@denotest/esm-import-cjs-default/1.0.0.tgz
 [UNORDERED_END]
diff --git a/tests/specs/npm/import_map/import_map/main.out b/tests/specs/npm/import_map/import_map/main.out
index 05f313d4e9..2698fb695c 100644
--- a/tests/specs/npm/import_map/import_map/main.out
+++ b/tests/specs/npm/import_map/import_map/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
 Download http://localhost:4260/chalk
-Download http://localhost:4260/@denotest/dual-cjs-esm
+Download http://localhost:4260/@denotest%2fdual-cjs-esm
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/dual-cjs-esm/1.0.0.tgz
diff --git a/tests/specs/npm/imports_package_json/imports_package_json/import_not_defined.out b/tests/specs/npm/imports_package_json/imports_package_json/import_not_defined.out
index 70d1145a37..abfa414030 100644
--- a/tests/specs/npm/imports_package_json/imports_package_json/import_not_defined.out
+++ b/tests/specs/npm/imports_package_json/imports_package_json/import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#not-defined" is not defined in package [WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json/imports_package_json/main.out b/tests/specs/npm/imports_package_json/imports_package_json/main.out
index 979e355765..70d787b251 100644
--- a/tests/specs/npm/imports_package_json/imports_package_json/main.out
+++ b/tests/specs/npm/imports_package_json/imports_package_json/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 hi
 bye
diff --git a/tests/specs/npm/imports_package_json/imports_package_json/sub_path_import_not_defined.out b/tests/specs/npm/imports_package_json/imports_package_json/sub_path_import_not_defined.out
index 7c803f2bf1..95524202ae 100644
--- a/tests/specs/npm/imports_package_json/imports_package_json/sub_path_import_not_defined.out
+++ b/tests/specs/npm/imports_package_json/imports_package_json/sub_path_import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#hi" is not defined in package [WILDCARD]sub_path[WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/import_not_defined.out b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/import_not_defined.out
index 70d1145a37..abfa414030 100644
--- a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/import_not_defined.out
+++ b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#not-defined" is not defined in package [WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/main.out b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/main.out
index 979e355765..70d787b251 100644
--- a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/main.out
+++ b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 hi
 bye
diff --git a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/sub_path_import_not_defined.out b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/sub_path_import_not_defined.out
index 7c803f2bf1..95524202ae 100644
--- a/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/sub_path_import_not_defined.out
+++ b/tests/specs/npm/imports_package_json_import_not_defined/imports_package_json/sub_path_import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#hi" is not defined in package [WILDCARD]sub_path[WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/import_not_defined.out b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/import_not_defined.out
index 70d1145a37..abfa414030 100644
--- a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/import_not_defined.out
+++ b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#not-defined" is not defined in package [WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/main.out b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/main.out
index 979e355765..70d787b251 100644
--- a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/main.out
+++ b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 hi
 bye
diff --git a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/sub_path_import_not_defined.out b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/sub_path_import_not_defined.out
index 7c803f2bf1..95524202ae 100644
--- a/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/sub_path_import_not_defined.out
+++ b/tests/specs/npm/imports_package_json_sub_path_import_not_defined/imports_package_json/sub_path_import_not_defined.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/imports-package-json
+Download http://localhost:4260/@denotest%2fimports-package-json
 Download http://localhost:4260/@denotest/imports-package-json/1.0.0.tgz
 error: [ERR_PACKAGE_IMPORT_NOT_DEFINED] Package import specifier "#hi" is not defined in package [WILDCARD]sub_path[WILDCARD]package.json imported from '[WILDCARD]import_not_defined.js'
diff --git a/tests/specs/npm/info_chalk_json/cjs_with_deps/main_info_json.out b/tests/specs/npm/info_chalk_json/cjs_with_deps/main_info_json.out
index 137b9f8ce5..2f7dde2d98 100644
--- a/tests/specs/npm/info_chalk_json/cjs_with_deps/main_info_json.out
+++ b/tests/specs/npm/info_chalk_json/cjs_with_deps/main_info_json.out
@@ -46,6 +46,16 @@
       "size": 325,
       "mediaType": "JavaScript",
       "specifier": "[WILDCARD]/main.js"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/chai@4.3.6",
+      "npmPackage": "chai@4.3.6"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/chalk@4.1.2",
+      "npmPackage": "chalk@4.1.2"
     }
   ],
   "redirects": {
@@ -58,12 +68,14 @@
       "version": "4.3.0",
       "dependencies": [
         "color-convert@2.0.1"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "assertion-error@1.1.0": {
       "name": "assertion-error",
       "version": "1.1.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "chai@4.3.6": {
       "name": "chai",
@@ -76,7 +88,8 @@
         "loupe@2.3.4",
         "pathval@1.1.1",
         "type-detect@4.0.8"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "chalk@4.1.2": {
       "name": "chalk",
@@ -84,65 +97,76 @@
       "dependencies": [
         "ansi-styles@4.3.0",
         "supports-color@7.2.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "check-error@1.0.2": {
       "name": "check-error",
       "version": "1.0.2",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-convert@2.0.1": {
       "name": "color-convert",
       "version": "2.0.1",
       "dependencies": [
         "color-name@1.1.4"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-name@1.1.4": {
       "name": "color-name",
       "version": "1.1.4",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "deep-eql@3.0.1": {
       "name": "deep-eql",
       "version": "3.0.1",
       "dependencies": [
         "type-detect@4.0.8"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "get-func-name@2.0.0": {
       "name": "get-func-name",
       "version": "2.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "has-flag@4.0.0": {
       "name": "has-flag",
       "version": "4.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "loupe@2.3.4": {
       "name": "loupe",
       "version": "2.3.4",
       "dependencies": [
         "get-func-name@2.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "pathval@1.1.1": {
       "name": "pathval",
       "version": "1.1.1",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "supports-color@7.2.0": {
       "name": "supports-color",
       "version": "7.2.0",
       "dependencies": [
         "has-flag@4.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "type-detect@4.0.8": {
       "name": "type-detect",
       "version": "4.0.8",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     }
   }
 }
diff --git a/tests/specs/npm/info_chalk_json_node_modules_dir/cjs_with_deps/main_info_json.out b/tests/specs/npm/info_chalk_json_node_modules_dir/cjs_with_deps/main_info_json.out
index 137b9f8ce5..2f7dde2d98 100644
--- a/tests/specs/npm/info_chalk_json_node_modules_dir/cjs_with_deps/main_info_json.out
+++ b/tests/specs/npm/info_chalk_json_node_modules_dir/cjs_with_deps/main_info_json.out
@@ -46,6 +46,16 @@
       "size": 325,
       "mediaType": "JavaScript",
       "specifier": "[WILDCARD]/main.js"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/chai@4.3.6",
+      "npmPackage": "chai@4.3.6"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/chalk@4.1.2",
+      "npmPackage": "chalk@4.1.2"
     }
   ],
   "redirects": {
@@ -58,12 +68,14 @@
       "version": "4.3.0",
       "dependencies": [
         "color-convert@2.0.1"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "assertion-error@1.1.0": {
       "name": "assertion-error",
       "version": "1.1.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "chai@4.3.6": {
       "name": "chai",
@@ -76,7 +88,8 @@
         "loupe@2.3.4",
         "pathval@1.1.1",
         "type-detect@4.0.8"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "chalk@4.1.2": {
       "name": "chalk",
@@ -84,65 +97,76 @@
       "dependencies": [
         "ansi-styles@4.3.0",
         "supports-color@7.2.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "check-error@1.0.2": {
       "name": "check-error",
       "version": "1.0.2",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-convert@2.0.1": {
       "name": "color-convert",
       "version": "2.0.1",
       "dependencies": [
         "color-name@1.1.4"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-name@1.1.4": {
       "name": "color-name",
       "version": "1.1.4",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "deep-eql@3.0.1": {
       "name": "deep-eql",
       "version": "3.0.1",
       "dependencies": [
         "type-detect@4.0.8"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "get-func-name@2.0.0": {
       "name": "get-func-name",
       "version": "2.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "has-flag@4.0.0": {
       "name": "has-flag",
       "version": "4.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "loupe@2.3.4": {
       "name": "loupe",
       "version": "2.3.4",
       "dependencies": [
         "get-func-name@2.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "pathval@1.1.1": {
       "name": "pathval",
       "version": "1.1.1",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "supports-color@7.2.0": {
       "name": "supports-color",
       "version": "7.2.0",
       "dependencies": [
         "has-flag@4.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "type-detect@4.0.8": {
       "name": "type-detect",
       "version": "4.0.8",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     }
   }
 }
diff --git a/tests/specs/npm/info_cli_chalk_json/info/chalk_json.out b/tests/specs/npm/info_cli_chalk_json/info/chalk_json.out
index 21fc7edf1a..fd2aa9ab0d 100644
--- a/tests/specs/npm/info_cli_chalk_json/info/chalk_json.out
+++ b/tests/specs/npm/info_cli_chalk_json/info/chalk_json.out
@@ -19,7 +19,8 @@
       "version": "4.3.0",
       "dependencies": [
         "color-convert@2.0.1"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "chalk@4.1.2": {
       "name": "chalk",
@@ -27,31 +28,36 @@
       "dependencies": [
         "ansi-styles@4.3.0",
         "supports-color@7.2.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-convert@2.0.1": {
       "name": "color-convert",
       "version": "2.0.1",
       "dependencies": [
         "color-name@1.1.4"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "color-name@1.1.4": {
       "name": "color-name",
       "version": "1.1.4",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "has-flag@4.0.0": {
       "name": "has-flag",
       "version": "4.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "supports-color@7.2.0": {
       "name": "supports-color",
       "version": "7.2.0",
       "dependencies": [
         "has-flag@4.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     }
   }
 }
diff --git a/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main.out b/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main.out
index 3c133bcde4..b7a5835577 100644
--- a/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main.out
+++ b/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main_node_modules_reload.out b/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main_node_modules_reload.out
index 9c81452118..18d7f7865b 100644
--- a/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main_node_modules_reload.out
+++ b/tests/specs/npm/info_peer_deps/peer_deps_with_copied_folders/main_node_modules_reload.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main.out b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main.out
index 3c133bcde4..b7a5835577 100644
--- a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main.out
+++ b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_info_json.out b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_info_json.out
index 46cc35c650..2ee6268f55 100644
--- a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_info_json.out
+++ b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_info_json.out
@@ -1,7 +1,7 @@
 {
   "version": 1,
   "roots": [
-    "[WILDCARD]/peer_deps_with_copied_folders/main.ts"
+    "file://[WILDCARD]/main.ts"
   ],
   "modules": [
     {
@@ -46,6 +46,16 @@
       "size": 171,
       "mediaType": "TypeScript",
       "specifier": "file://[WILDCARD]/main.ts"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/@denotest/peer-dep-test-child@1.0.0",
+      "npmPackage": "@denotest/peer-dep-test-child@1.0.0_@denotest+peer-dep-test-peer@1.0.0"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/@denotest/peer-dep-test-child@2.0.0",
+      "npmPackage": "@denotest/peer-dep-test-child@2.0.0_@denotest+peer-dep-test-peer@2.0.0"
     }
   ],
   "redirects": {
@@ -59,7 +69,8 @@
       "dependencies": [
         "@denotest/peer-dep-test-grandchild@1.0.0_@denotest+peer-dep-test-peer@1.0.0",
         "@denotest/peer-dep-test-peer@1.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-child@2.0.0_@denotest+peer-dep-test-peer@2.0.0": {
       "name": "@denotest/peer-dep-test-child",
@@ -67,31 +78,36 @@
       "dependencies": [
         "@denotest/peer-dep-test-grandchild@1.0.0_@denotest+peer-dep-test-peer@2.0.0",
         "@denotest/peer-dep-test-peer@2.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-grandchild@1.0.0_@denotest+peer-dep-test-peer@1.0.0": {
       "name": "@denotest/peer-dep-test-grandchild",
       "version": "1.0.0",
       "dependencies": [
         "@denotest/peer-dep-test-peer@1.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-grandchild@1.0.0_@denotest+peer-dep-test-peer@2.0.0": {
       "name": "@denotest/peer-dep-test-grandchild",
       "version": "1.0.0",
       "dependencies": [
         "@denotest/peer-dep-test-peer@2.0.0"
-      ]
+      ],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-peer@1.0.0": {
       "name": "@denotest/peer-dep-test-peer",
       "version": "1.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     },
     "@denotest/peer-dep-test-peer@2.0.0": {
       "name": "@denotest/peer-dep-test-peer",
       "version": "2.0.0",
-      "dependencies": []
+      "dependencies": [],
+      "registryUrl": "http://localhost:4260/"
     }
   }
 }
diff --git a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_node_modules_reload.out b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_node_modules_reload.out
index 9c81452118..18d7f7865b 100644
--- a/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_node_modules_reload.out
+++ b/tests/specs/npm/info_peer_deps_json/peer_deps_with_copied_folders/main_node_modules_reload.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/specs/npm/lifecycle_scripts/__test__.jsonc b/tests/specs/npm/lifecycle_scripts/__test__.jsonc
index b798b968ff..589c131dda 100644
--- a/tests/specs/npm/lifecycle_scripts/__test__.jsonc
+++ b/tests/specs/npm/lifecycle_scripts/__test__.jsonc
@@ -5,7 +5,7 @@
       "steps": [
         {
           "args": "cache --allow-scripts=npm:@denotest/node-addon main.js",
-          "output": "[WILDCARD]gyp info ok \n"
+          "output": "[WILDCARD]Initialize @denotest/node-addon@1.0.0: running 'install' script\n"
         },
         {
           "args": "run -A main.js",
@@ -38,7 +38,7 @@
       "steps": [
         {
           // without running scripts (should warn)
-          "args": "cache all_lifecycles.js",
+          "args": "run all_lifecycles.js",
           "output": "all_lifecycles_not_run.out"
         },
         {
@@ -51,6 +51,23 @@
         }
       ]
     },
+    "deno_run_lifecycle_scripts": {
+      "steps": [
+        {
+          // without running scripts (should warn)
+          "args": "run all_lifecycles.js",
+          "output": "all_lifecycles_not_run.out"
+        },
+        {
+          // now run scripts
+          "args": "run --allow-scripts all_lifecycles.js",
+          // this test package covers running preinstall, install, and postinstall scripts
+          // it also exercises running bin packages (esbuild in this case), using `node` in a script
+          // (with and without node-only CLI flags), and using `npx` in a script
+          "output": "all_lifecycles_deno_run.out"
+        }
+      ]
+    },
     "global_lifecycle_scripts": {
       "steps": [
         {
@@ -79,14 +96,12 @@
         {
           // without running scripts (should warn)
           "args": "run all_lifecycles.js",
-          "output": "only_warns_first1.out",
-          "exitCode": 1
+          "output": "only_warns_first1.out"
         },
         {
           // without running scripts (does not warn)
           "args": "run all_lifecycles.js",
-          "output": "only_warns_first2.out",
-          "exitCode": 1
+          "output": "only_warns_first2.out"
         },
         {
           // should warn because this is an explicit install
@@ -128,6 +143,13 @@
           // we run the install script, we should use the correct binary (relative to the package)
           "args": "cache --allow-scripts conflicting_bin.js",
           "output": "conflicting_bin.out"
+        },
+        {
+          "args": [
+            "eval",
+            "console.log(Deno.readTextFileSync('./say-hello-output.txt'))"
+          ],
+          "output": "conflicting_bin2.out"
         }
       ]
     },
diff --git a/tests/specs/npm/lifecycle_scripts/all_lifecycles.out b/tests/specs/npm/lifecycle_scripts/all_lifecycles.out
index 956c006ddc..bdbb2b08ea 100644
--- a/tests/specs/npm/lifecycle_scripts/all_lifecycles.out
+++ b/tests/specs/npm/lifecycle_scripts/all_lifecycles.out
@@ -1,14 +1,3 @@
-preinstall
-deno preinstall.js
-node preinstall.js
-install
-hello from install script
-postinstall[WILDCARD]
- _____________
-< postinstall >
- -------------
-        \   ^__^
-         \  (oo)\_______
-            (__)\       )\/\
-                ||----w |
-                ||     ||
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'preinstall' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'install' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'postinstall' script
diff --git a/tests/specs/npm/lifecycle_scripts/all_lifecycles_deno_run.out b/tests/specs/npm/lifecycle_scripts/all_lifecycles_deno_run.out
new file mode 100644
index 0000000000..5f06f6214c
--- /dev/null
+++ b/tests/specs/npm/lifecycle_scripts/all_lifecycles_deno_run.out
@@ -0,0 +1,4 @@
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'preinstall' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'install' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'postinstall' script
+value is 42
diff --git a/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run.out b/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run.out
index 09324c8452..645556b26d 100644
--- a/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run.out
+++ b/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/node-lifecycle-scripts@1.0.0
@@ -12,3 +12,4 @@ Warning The following packages contained npm lifecycle scripts (preinstall/insta
 ┠─ This may cause the packages to not work correctly.
 ┖─ To run lifecycle scripts, use the `--allow-scripts` flag with `deno install`:
    deno install --allow-scripts=npm:@denotest/node-lifecycle-scripts@1.0.0
+value is 42
diff --git a/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run_global.out b/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run_global.out
index 93b5a14cc0..1b06bccb8a 100644
--- a/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run_global.out
+++ b/tests/specs/npm/lifecycle_scripts/all_lifecycles_not_run_global.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 [UNORDERED_END]
diff --git a/tests/specs/npm/lifecycle_scripts/conflicting_bin.out b/tests/specs/npm/lifecycle_scripts/conflicting_bin.out
index c70aafdd53..33282ee81c 100644
--- a/tests/specs/npm/lifecycle_scripts/conflicting_bin.out
+++ b/tests/specs/npm/lifecycle_scripts/conflicting_bin.out
@@ -1,13 +1,12 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/better-say-hello
-Download http://localhost:4260/@denotest/say-hello-on-install
-Download http://localhost:4260/@denotest/say-hello
+Download http://localhost:4260/@denotest%2fbetter-say-hello
+Download http://localhost:4260/@denotest%2fsay-hello-on-install
+Download http://localhost:4260/@denotest%2fsay-hello
 Download http://localhost:4260/@denotest/better-say-hello/1.0.0.tgz
 Download http://localhost:4260/@denotest/say-hello-on-install/1.0.0.tgz
 Download http://localhost:4260/@denotest/say-hello/1.0.0.tgz
 Initialize @denotest/better-say-hello@1.0.0
 Initialize @denotest/say-hello-on-install@1.0.0
 Initialize @denotest/say-hello@1.0.0
+Initialize @denotest/say-hello-on-install@1.0.0: running 'install' script
 [UNORDERED_END]
-install script
-@denotest/say-hello says hello!
diff --git a/tests/specs/npm/lifecycle_scripts/conflicting_bin2.out b/tests/specs/npm/lifecycle_scripts/conflicting_bin2.out
new file mode 100644
index 0000000000..b4640b02c5
--- /dev/null
+++ b/tests/specs/npm/lifecycle_scripts/conflicting_bin2.out
@@ -0,0 +1 @@
+@denotest/say-hello says hello!
diff --git a/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles.out b/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles.out
index f62079d3fe..bdbb2b08ea 100644
--- a/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles.out
+++ b/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles.out
@@ -1,15 +1,3 @@
-preinstall
-deno preinstall.js
-node preinstall.js
-install
-hello from install script
-postinstall
-[WILDCARD]
- _____________
-< postinstall >
- -------------
-        \   ^__^
-         \  (oo)\_______
-            (__)\       )\/\
-                ||----w |
-                ||     ||
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'preinstall' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'install' script
+Initialize @denotest/node-lifecycle-scripts@1.0.0: running 'postinstall' script
diff --git a/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles_not_run.out b/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles_not_run.out
index 09324c8452..d72f3c8b2d 100644
--- a/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles_not_run.out
+++ b/tests/specs/npm/lifecycle_scripts/future_install_all_lifecycles_not_run.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/node-lifecycle-scripts@1.0.0
diff --git a/tests/specs/npm/lifecycle_scripts/no_deno_json.out b/tests/specs/npm/lifecycle_scripts/no_deno_json.out
index 38a4614494..1966396a31 100644
--- a/tests/specs/npm/lifecycle_scripts/no_deno_json.out
+++ b/tests/specs/npm/lifecycle_scripts/no_deno_json.out
@@ -1,11 +1,10 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/lifecycle-scripts-cjs
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2flifecycle-scripts-cjs
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/lifecycle-scripts-cjs/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/lifecycle-scripts-cjs@1.0.0
 Initialize @denotest/bin@1.0.0
+Initialize @denotest/lifecycle-scripts-cjs@1.0.0: running 'preinstall' script
+Initialize @denotest/lifecycle-scripts-cjs@1.0.0: running 'install' script
 [UNORDERED_END]
-preinstall
-install
-hello from install script
diff --git a/tests/specs/npm/lifecycle_scripts/node_gyp_not_found.out b/tests/specs/npm/lifecycle_scripts/node_gyp_not_found.out
index 06c856cd94..339384f732 100644
--- a/tests/specs/npm/lifecycle_scripts/node_gyp_not_found.out
+++ b/tests/specs/npm/lifecycle_scripts/node_gyp_not_found.out
@@ -1,9 +1,12 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-addon-implicit-node-gyp
+Download http://localhost:4260/@denotest%2fnode-addon-implicit-node-gyp
 Download http://localhost:4260/@denotest/node-addon-implicit-node-gyp/1.0.0.tgz
 Initialize @denotest/node-addon-implicit-node-gyp@1.0.0
+Initialize @denotest/node-addon-implicit-node-gyp@1.0.0: running 'install' script
 [UNORDERED_END]
 Warning node-gyp was used in a script, but was not listed as a dependency. Either add it as a dependency or install it globally (e.g. `npm install -g node-gyp`)
-[WILDCARD]
 error: script 'install' in '@denotest/node-addon-implicit-node-gyp@1.0.0' failed with exit code 1
+stderr:
+Error launching 'node-gyp': [WILDCARD]
+
 error: failed to run scripts for packages: @denotest/node-addon-implicit-node-gyp@1.0.0
diff --git a/tests/specs/npm/lifecycle_scripts/node_gyp_not_run.out b/tests/specs/npm/lifecycle_scripts/node_gyp_not_run.out
index e0e51b26c0..da5bb4f7b5 100644
--- a/tests/specs/npm/lifecycle_scripts/node_gyp_not_run.out
+++ b/tests/specs/npm/lifecycle_scripts/node_gyp_not_run.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/node-addon
+Download http://localhost:4260/@denotest%2fnode-addon
 Download http://localhost:4260/node-gyp
 [WILDCARD]
 Warning The following packages contained npm lifecycle scripts (preinstall/install/postinstall) that were not executed:
diff --git a/tests/specs/npm/lifecycle_scripts/only_warns_first1.out b/tests/specs/npm/lifecycle_scripts/only_warns_first1.out
index 947777b5ba..645556b26d 100644
--- a/tests/specs/npm/lifecycle_scripts/only_warns_first1.out
+++ b/tests/specs/npm/lifecycle_scripts/only_warns_first1.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/node-lifecycle-scripts
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fnode-lifecycle-scripts
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/node-lifecycle-scripts/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/node-lifecycle-scripts@1.0.0
@@ -12,5 +12,4 @@ Warning The following packages contained npm lifecycle scripts (preinstall/insta
 ┠─ This may cause the packages to not work correctly.
 ┖─ To run lifecycle scripts, use the `--allow-scripts` flag with `deno install`:
    deno install --allow-scripts=npm:@denotest/node-lifecycle-scripts@1.0.0
-error: Uncaught SyntaxError: The requested module 'npm:@denotest/node-lifecycle-scripts' does not provide an export named 'value'
-[WILDCARD]
+value is 42
diff --git a/tests/specs/npm/lifecycle_scripts/only_warns_first2.out b/tests/specs/npm/lifecycle_scripts/only_warns_first2.out
index f6a02c7279..9e78061598 100644
--- a/tests/specs/npm/lifecycle_scripts/only_warns_first2.out
+++ b/tests/specs/npm/lifecycle_scripts/only_warns_first2.out
@@ -1,3 +1 @@
-[# note no warning]
-error: Uncaught SyntaxError: The requested module 'npm:@denotest/node-lifecycle-scripts' does not provide an export named 'value'
-[WILDCARD]
+value is 42
diff --git a/tests/specs/npm/lossy_utf8_module/main.out b/tests/specs/npm/lossy_utf8_module/main.out
index 0e96f9ebb3..d046d2ec55 100644
--- a/tests/specs/npm/lossy_utf8_module/main.out
+++ b/tests/specs/npm/lossy_utf8_module/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/lossy-utf8-module
+Download http://localhost:4260/@denotest%2flossy-utf8-module
 Download http://localhost:4260/@denotest/lossy-utf8-module/1.0.0.tgz
 ����
diff --git a/tests/specs/npm/lossy_utf8_package_json/main.out b/tests/specs/npm/lossy_utf8_package_json/main.out
index 99aa5ab61f..69f6870392 100644
--- a/tests/specs/npm/lossy_utf8_package_json/main.out
+++ b/tests/specs/npm/lossy_utf8_package_json/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/lossy-utf8-package-json
+Download http://localhost:4260/@denotest%2flossy-utf8-package-json
 Download http://localhost:4260/@denotest/lossy-utf8-package-json/1.0.0.tgz
 hello
diff --git a/tests/specs/npm/lossy_utf8_script/main.out b/tests/specs/npm/lossy_utf8_script/main.out
index 180ecdf1c3..0883392fd9 100644
--- a/tests/specs/npm/lossy_utf8_script/main.out
+++ b/tests/specs/npm/lossy_utf8_script/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/lossy-utf8-script
+Download http://localhost:4260/@denotest%2flossy-utf8-script
 Download http://localhost:4260/@denotest/lossy-utf8-script/1.0.0.tgz
 ����
diff --git a/tests/specs/npm/lossy_utf8_script_from_cjs/main.out b/tests/specs/npm/lossy_utf8_script_from_cjs/main.out
index 4f062a2aef..635ea5b3a1 100644
--- a/tests/specs/npm/lossy_utf8_script_from_cjs/main.out
+++ b/tests/specs/npm/lossy_utf8_script_from_cjs/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/lossy-utf8-script
+Download http://localhost:4260/@denotest%2flossy-utf8-script
 Download http://localhost:4260/@denotest/lossy-utf8-script/1.0.0.tgz
 Initialize @denotest/lossy-utf8-script@1.0.0
 ����
diff --git a/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/global.out b/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/global.out
index fdacea3852..a1d3a6e2c5 100644
--- a/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/global.out
+++ b/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/global.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/MixedCase
-Download http://localhost:4260/@denotest/CAPITALS
+Download http://localhost:4260/@denotest%2fMixedCase
+Download http://localhost:4260/@denotest%2fCAPITALS
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/CAPITALS/1.0.0.tgz
diff --git a/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/local.out b/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/local.out
index 6ab989d80c..c8c9ed396c 100644
--- a/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/local.out
+++ b/tests/specs/npm/mixed_case_package_name_global_dir/mixed_case_package_name/local.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/MixedCase
-Download http://localhost:4260/@denotest/CAPITALS
+Download http://localhost:4260/@denotest%2fMixedCase
+Download http://localhost:4260/@denotest%2fCAPITALS
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/CAPITALS/1.0.0.tgz
diff --git a/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/global.out b/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/global.out
index fdacea3852..a1d3a6e2c5 100644
--- a/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/global.out
+++ b/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/global.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/MixedCase
-Download http://localhost:4260/@denotest/CAPITALS
+Download http://localhost:4260/@denotest%2fMixedCase
+Download http://localhost:4260/@denotest%2fCAPITALS
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/CAPITALS/1.0.0.tgz
diff --git a/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/local.out b/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/local.out
index 6ab989d80c..c8c9ed396c 100644
--- a/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/local.out
+++ b/tests/specs/npm/mixed_case_package_name_local_dir/mixed_case_package_name/local.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/MixedCase
-Download http://localhost:4260/@denotest/CAPITALS
+Download http://localhost:4260/@denotest%2fMixedCase
+Download http://localhost:4260/@denotest%2fCAPITALS
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/CAPITALS/1.0.0.tgz
diff --git a/tests/specs/npm/no_types_cjs/main.out b/tests/specs/npm/no_types_cjs/main.out
index 4747a9a325..c993d5fbf4 100644
--- a/tests/specs/npm/no_types_cjs/main.out
+++ b/tests/specs/npm/no_types_cjs/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/no-types-cjs
+Download http://localhost:4260/@denotest%2fno-types-cjs
 Download http://localhost:4260/@denotest/no-types-cjs/1.0.0.tgz
 Check file:///[WILDLINE]/no_types_cjs/main.ts
diff --git a/tests/specs/npm/no_types_in_conditional_exports/main.out b/tests/specs/npm/no_types_in_conditional_exports/main.out
index 46c5832347..593cb23370 100644
--- a/tests/specs/npm/no_types_in_conditional_exports/main.out
+++ b/tests/specs/npm/no_types_in_conditional_exports/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/no-types-in-conditional-exports
+Download http://localhost:4260/@denotest%2fno-types-in-conditional-exports
 Download http://localhost:4260/@denotest/no-types-in-conditional-exports/1.0.0.tgz
 Check [WILDCARD]npm/no_types_in_conditional_exports/main.ts
 { foo: "bar" }
diff --git a/tests/specs/npm/node_modules_import/install.out b/tests/specs/npm/node_modules_import/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/npm/node_modules_import/install.out
+++ b/tests/specs/npm/node_modules_import/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/npm/node_modules_import_auto/main.out b/tests/specs/npm/node_modules_import_auto/main.out
index 8fda5cda1e..18194e3a0c 100644
--- a/tests/specs/npm/node_modules_import_auto/main.out
+++ b/tests/specs/npm/node_modules_import_auto/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 2
diff --git a/tests/specs/npm/node_modules_import_auto/main_check.out b/tests/specs/npm/node_modules_import_auto/main_check.out
index 24249f357b..093b0c051a 100644
--- a/tests/specs/npm/node_modules_import_auto/main_check.out
+++ b/tests/specs/npm/node_modules_import_auto/main_check.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file:///[WILDCARD]/main.ts
diff --git a/tests/specs/npm/non_existent_dep/__test__.jsonc b/tests/specs/npm/non_existent_dep/__test__.jsonc
index bc38414195..8608e00f3e 100644
--- a/tests/specs/npm/non_existent_dep/__test__.jsonc
+++ b/tests/specs/npm/non_existent_dep/__test__.jsonc
@@ -1,5 +1,5 @@
 {
   "args": "cache npm:@denotest/non-existent-dep",
   "exitCode": 1,
-  "output": "[UNORDERED_START]\nDownload http://localhost:4260/@denotest/non-existent-dep\nDownload http://localhost:4260/@denotest/non-existent\n[UNORDERED_END]\nerror: npm package '@denotest/non-existent' does not exist.\n"
+  "output": "[UNORDERED_START]\nDownload http://localhost:4260/@denotest%2fnon-existent-dep\nDownload http://localhost:4260/@denotest%2fnon-existent\n[UNORDERED_END]\nerror: npm package '@denotest/non-existent' does not exist.\n"
 }
diff --git a/tests/specs/npm/non_existent_dep_version/__test__.jsonc b/tests/specs/npm/non_existent_dep_version/__test__.jsonc
index 4bc084ce3d..dd91c66243 100644
--- a/tests/specs/npm/non_existent_dep_version/__test__.jsonc
+++ b/tests/specs/npm/non_existent_dep_version/__test__.jsonc
@@ -1,5 +1,5 @@
 {
   "args": "cache npm:@denotest/non-existent-dep-version",
   "exitCode": 1,
-  "output": "[UNORDERED_START]\nDownload http://localhost:4260/@denotest/non-existent-dep-version\nDownload http://localhost:4260/@denotest/esm-basic\n[UNORDERED_END]\nerror: Could not find npm package '@denotest/esm-basic' matching '=99.99.99'.\n"
+  "output": "[UNORDERED_START]\nDownload http://localhost:4260/@denotest%2fnon-existent-dep-version\nDownload http://localhost:4260/@denotest%2fesm-basic\n[UNORDERED_END]\nerror: Could not find npm package '@denotest/esm-basic' matching '=99.99.99'.\n"
 }
diff --git a/tests/specs/npm/npmrc/__test__.jsonc b/tests/specs/npm/npmrc/__test__.jsonc
index e7588a7797..88ef2d8102 100644
--- a/tests/specs/npm/npmrc/__test__.jsonc
+++ b/tests/specs/npm/npmrc/__test__.jsonc
@@ -13,6 +13,10 @@
     "run_node_modules_dir": {
       "args": "run --node-modules-dir=auto -A --quiet main.js",
       "output": "main.out"
+    },
+    "info": {
+      "args": "info --node-modules-dir=auto --json main.js",
+      "output": "info.out"
     }
   }
 }
diff --git a/tests/specs/npm/npmrc/info.out b/tests/specs/npm/npmrc/info.out
new file mode 100644
index 0000000000..ee9aa9ee96
--- /dev/null
+++ b/tests/specs/npm/npmrc/info.out
@@ -0,0 +1,87 @@
+[UNORDERED_START]
+Download http://localhost:4262/@denotest2%2fbasic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4261/@denotest/basic/1.0.0.tgz
+Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
+[UNORDERED_END]
+[UNORDERED_START]
+Initialize @denotest/basic@1.0.0
+Initialize @denotest2/basic@1.0.0
+[UNORDERED_END]
+{
+  "version": 1,
+  "roots": [
+    "file://[WILDCARD]/main.js"
+  ],
+  "modules": [
+    {
+      "kind": "esm",
+      "dependencies": [
+        {
+          "specifier": "@denotest/basic",
+          "code": {
+            "specifier": "npm:@denotest/basic@1.0.0",
+            "span": {
+              "start": {
+                "line": 0,
+                "character": 35
+              },
+              "end": {
+                "line": 0,
+                "character": 52
+              }
+            }
+          }
+        },
+        {
+          "specifier": "@denotest2/basic",
+          "code": {
+            "specifier": "npm:@denotest2/basic@1.0.0",
+            "span": {
+              "start": {
+                "line": 1,
+                "character": 22
+              },
+              "end": {
+                "line": 1,
+                "character": 40
+              }
+            }
+          }
+        }
+      ],
+      "local": "[WILDCARD]main.js",
+      "size": 192,
+      "mediaType": "JavaScript",
+      "specifier": "file://[WILDCARD]/main.js"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/@denotest/basic@1.0.0",
+      "npmPackage": "@denotest/basic@1.0.0"
+    },
+    {
+      "kind": "npm",
+      "specifier": "npm:/@denotest2/basic@1.0.0",
+      "npmPackage": "@denotest2/basic@1.0.0"
+    }
+  ],
+  "redirects": {
+    "npm:@denotest/basic@1.0.0": "npm:/@denotest/basic@1.0.0",
+    "npm:@denotest2/basic@1.0.0": "npm:/@denotest2/basic@1.0.0"
+  },
+  "npmPackages": {
+    "@denotest/basic@1.0.0": {
+      "name": "@denotest/basic",
+      "version": "1.0.0",
+      "dependencies": [],
+      "registryUrl": "http://localhost:4261/"
+    },
+    "@denotest2/basic@1.0.0": {
+      "name": "@denotest2/basic",
+      "version": "1.0.0",
+      "dependencies": [],
+      "registryUrl": "http://localhost:4262/"
+    }
+  }
+}
diff --git a/tests/specs/npm/npmrc/install.out b/tests/specs/npm/npmrc/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/npm/npmrc/install.out
+++ b/tests/specs/npm/npmrc/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_bad_registry_config/main.out b/tests/specs/npm/npmrc_bad_registry_config/main.out
index 990d4a47fa..5d778d32e9 100644
--- a/tests/specs/npm/npmrc_bad_registry_config/main.out
+++ b/tests/specs/npm/npmrc_bad_registry_config/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4261/@denotest/basic
-error: Error getting response at http://localhost:4261/@denotest/basic for package "@denotest/basic": Bad response: 401
+Download http://localhost:4261/@denotest%2fbasic
+error: Error getting response at http://localhost:4261/@denotest%2fbasic for package "@denotest/basic": Bad response: 401
 [WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/npm/npmrc_bad_token/main.out b/tests/specs/npm/npmrc_bad_token/main.out
index 990d4a47fa..5d778d32e9 100644
--- a/tests/specs/npm/npmrc_bad_token/main.out
+++ b/tests/specs/npm/npmrc_bad_token/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4261/@denotest/basic
-error: Error getting response at http://localhost:4261/@denotest/basic for package "@denotest/basic": Bad response: 401
+Download http://localhost:4261/@denotest%2fbasic
+error: Error getting response at http://localhost:4261/@denotest%2fbasic for package "@denotest/basic": Bad response: 401
 [WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/npm/npmrc_basic_auth/install.out b/tests/specs/npm/npmrc_basic_auth/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/npm/npmrc_basic_auth/install.out
+++ b/tests/specs/npm/npmrc_basic_auth/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_deno_json/main.out b/tests/specs/npm/npmrc_deno_json/main.out
index 62750088bd..c3d6be8a1a 100644
--- a/tests/specs/npm/npmrc_deno_json/main.out
+++ b/tests/specs/npm/npmrc_deno_json/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4261/@denotest/basic
+Download http://localhost:4261/@denotest%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 0
 42
diff --git a/tests/specs/npm/npmrc_homedir/install.out b/tests/specs/npm/npmrc_homedir/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/npm/npmrc_homedir/install.out
+++ b/tests/specs/npm/npmrc_homedir/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_install_arg/.npmrc b/tests/specs/npm/npmrc_install_arg/.npmrc
new file mode 100644
index 0000000000..de3704b924
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/.npmrc
@@ -0,0 +1,2 @@
+@denotest:registry=http://localhost:4261/
+//localhost:4261/:_authToken=private-reg-token
diff --git a/tests/specs/npm/npmrc_install_arg/__test__.jsonc b/tests/specs/npm/npmrc_install_arg/__test__.jsonc
new file mode 100644
index 0000000000..f34cfe116a
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/__test__.jsonc
@@ -0,0 +1,23 @@
+{
+  "tempDir": true,
+  "tests": {
+    "deno_install_add": {
+      "steps": [{
+        "args": "install npm:@denotest/basic",
+        "output": "install.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    },
+    "deno_add": {
+      "steps": [{
+        "args": "add npm:@denotest/basic",
+        "output": "add.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/npm/npmrc_install_arg/add.out b/tests/specs/npm/npmrc_install_arg/add.out
new file mode 100644
index 0000000000..11948e54d5
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/add.out
@@ -0,0 +1,4 @@
+Add npm:@denotest/basic@1.0.0
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4261/@denotest/basic/1.0.0.tgz
+Initialize @denotest/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_install_arg/install.out b/tests/specs/npm/npmrc_install_arg/install.out
new file mode 100644
index 0000000000..11948e54d5
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/install.out
@@ -0,0 +1,4 @@
+Add npm:@denotest/basic@1.0.0
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4261/@denotest/basic/1.0.0.tgz
+Initialize @denotest/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_install_arg/main.js b/tests/specs/npm/npmrc_install_arg/main.js
new file mode 100644
index 0000000000..e8ccf7611c
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/main.js
@@ -0,0 +1,5 @@
+import { getValue, setValue } from "@denotest/basic";
+
+console.log(getValue());
+setValue(42);
+console.log(getValue());
diff --git a/tests/specs/npm/npmrc_install_arg/main.out b/tests/specs/npm/npmrc_install_arg/main.out
new file mode 100644
index 0000000000..dcd912c89f
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/main.out
@@ -0,0 +1,2 @@
+0
+42
diff --git a/tests/specs/npm/npmrc_install_arg/package.json b/tests/specs/npm/npmrc_install_arg/package.json
new file mode 100644
index 0000000000..c1318b361a
--- /dev/null
+++ b/tests/specs/npm/npmrc_install_arg/package.json
@@ -0,0 +1,5 @@
+{
+  "name": "npmrc_test",
+  "version": "0.0.1",
+  "dependencies": {}
+}
diff --git a/tests/specs/npm/npmrc_no_auth/.npmrc b/tests/specs/npm/npmrc_no_auth/.npmrc
new file mode 100644
index 0000000000..860a7c3d9a
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/.npmrc
@@ -0,0 +1 @@
+@denotest3:registry=http://localhost:4263/
diff --git a/tests/specs/npm/npmrc_no_auth/__test__.jsonc b/tests/specs/npm/npmrc_no_auth/__test__.jsonc
new file mode 100644
index 0000000000..efd04f0e46
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/__test__.jsonc
@@ -0,0 +1,23 @@
+{
+  "tempDir": true,
+  "tests": {
+    "deno_install_arg": {
+      "steps": [{
+        "args": "install npm:@denotest3/basic",
+        "output": "install.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    },
+    "deno_add_arg": {
+      "steps": [{
+        "args": "add npm:@denotest3/basic",
+        "output": "add.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/npm/npmrc_no_auth/add.out b/tests/specs/npm/npmrc_no_auth/add.out
new file mode 100644
index 0000000000..31b34da13f
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/add.out
@@ -0,0 +1,4 @@
+Add npm:@denotest3/basic@1.0.0
+Download http://localhost:4263/@denotest3%2fbasic
+Download http://localhost:4263/@denotest3/basic/1.0.0.tgz
+Initialize @denotest3/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_no_auth/install.out b/tests/specs/npm/npmrc_no_auth/install.out
new file mode 100644
index 0000000000..31b34da13f
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/install.out
@@ -0,0 +1,4 @@
+Add npm:@denotest3/basic@1.0.0
+Download http://localhost:4263/@denotest3%2fbasic
+Download http://localhost:4263/@denotest3/basic/1.0.0.tgz
+Initialize @denotest3/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_no_auth/main.js b/tests/specs/npm/npmrc_no_auth/main.js
new file mode 100644
index 0000000000..22713bb0da
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/main.js
@@ -0,0 +1,5 @@
+import { getValue, setValue } from "@denotest3/basic";
+
+console.log(getValue());
+setValue(42);
+console.log(getValue());
diff --git a/tests/specs/npm/npmrc_no_auth/main.out b/tests/specs/npm/npmrc_no_auth/main.out
new file mode 100644
index 0000000000..dcd912c89f
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/main.out
@@ -0,0 +1,2 @@
+0
+42
diff --git a/tests/specs/npm/npmrc_no_auth/package.json b/tests/specs/npm/npmrc_no_auth/package.json
new file mode 100644
index 0000000000..dddaaac464
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth/package.json
@@ -0,0 +1,6 @@
+{
+  "name": "npmrc_test",
+  "version": "0.0.1",
+  "dependencies": {
+  }
+}
diff --git a/tests/specs/npm/npmrc_no_auth_install/.npmrc b/tests/specs/npm/npmrc_no_auth_install/.npmrc
new file mode 100644
index 0000000000..860a7c3d9a
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/.npmrc
@@ -0,0 +1 @@
+@denotest3:registry=http://localhost:4263/
diff --git a/tests/specs/npm/npmrc_no_auth_install/__test__.jsonc b/tests/specs/npm/npmrc_no_auth_install/__test__.jsonc
new file mode 100644
index 0000000000..56a598e3b9
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/__test__.jsonc
@@ -0,0 +1,14 @@
+{
+  "tempDir": true,
+  "tests": {
+    "deno_install_arg": {
+      "steps": [{
+        "args": "install",
+        "output": "install.out"
+      }, {
+        "args": "run -A main.js",
+        "output": "main.out"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/npm/npmrc_no_auth_install/install.out b/tests/specs/npm/npmrc_no_auth_install/install.out
new file mode 100644
index 0000000000..b82747af79
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/install.out
@@ -0,0 +1,3 @@
+Download http://localhost:4263/@denotest3%2fbasic
+Download http://localhost:4263/@denotest3/basic/1.0.0.tgz
+Initialize @denotest3/basic@1.0.0
diff --git a/tests/specs/npm/npmrc_no_auth_install/main.js b/tests/specs/npm/npmrc_no_auth_install/main.js
new file mode 100644
index 0000000000..22713bb0da
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/main.js
@@ -0,0 +1,5 @@
+import { getValue, setValue } from "@denotest3/basic";
+
+console.log(getValue());
+setValue(42);
+console.log(getValue());
diff --git a/tests/specs/npm/npmrc_no_auth_install/main.out b/tests/specs/npm/npmrc_no_auth_install/main.out
new file mode 100644
index 0000000000..dcd912c89f
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/main.out
@@ -0,0 +1,2 @@
+0
+42
diff --git a/tests/specs/npm/npmrc_no_auth_install/package.json b/tests/specs/npm/npmrc_no_auth_install/package.json
new file mode 100644
index 0000000000..2d4fb15bae
--- /dev/null
+++ b/tests/specs/npm/npmrc_no_auth_install/package.json
@@ -0,0 +1,7 @@
+{
+  "name": "npmrc_test",
+  "version": "0.0.1",
+  "dependencies": {
+    "@denotest3/basic": "1.0.0"
+  }
+}
diff --git a/tests/specs/npm/npmrc_not_next_to_package_json/main.out b/tests/specs/npm/npmrc_not_next_to_package_json/main.out
index b583868ffb..b128959a7c 100644
--- a/tests/specs/npm/npmrc_not_next_to_package_json/main.out
+++ b/tests/specs/npm/npmrc_not_next_to_package_json/main.out
@@ -2,7 +2,7 @@
 [# that serves the same packages. The important bit is the message below.]
 [WILDCARD] No .npmrc file found
 [WILDCARD]
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 [WILDCARD]
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 [WILDCARD]
diff --git a/tests/specs/npm/npmrc_password_no_username/install.out b/tests/specs/npm/npmrc_password_no_username/install.out
index d49a2ba0d8..b198bcd27e 100644
--- a/tests/specs/npm/npmrc_password_no_username/install.out
+++ b/tests/specs/npm/npmrc_password_no_username/install.out
@@ -1,3 +1,3 @@
 [UNORDERED_START]
-error: Error getting response at http://localhost:4261/@denotest/basic for package "@denotest/basic": Both the username and password must be provided for basic auth
+error: Error getting response at http://localhost:4261/@denotest%2fbasic for package "@denotest/basic": Both the username and password must be provided for basic auth
 [UNORDERED_END]
diff --git a/tests/specs/npm/npmrc_tarball_other_server/fail/main.out b/tests/specs/npm/npmrc_tarball_other_server/fail/main.out
index 08a84a477c..2c68dba54e 100644
--- a/tests/specs/npm/npmrc_tarball_other_server/fail/main.out
+++ b/tests/specs/npm/npmrc_tarball_other_server/fail/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4261/@denotest/tarballs-privateserver2
+Download http://localhost:4261/@denotest%2ftarballs-privateserver2
 Download http://localhost:4262/@denotest/tarballs-privateserver2/1.0.0.tgz
 error: Failed caching npm package '@denotest/tarballs-privateserver2@1.0.0'.
 
diff --git a/tests/specs/npm/npmrc_tarball_other_server/success/main.out b/tests/specs/npm/npmrc_tarball_other_server/success/main.out
index d75f26e336..5322a1a17d 100644
--- a/tests/specs/npm/npmrc_tarball_other_server/success/main.out
+++ b/tests/specs/npm/npmrc_tarball_other_server/success/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4261/@denotest/tarballs-privateserver2
+Download http://localhost:4261/@denotest%2ftarballs-privateserver2
 Download http://localhost:4262/@denotest/tarballs-privateserver2/1.0.0.tgz
 [# This fails on a checksum issue, because the test server isn't smart enough]
 [# to serve proper checksums for a package at another registry. That's fine]
diff --git a/tests/specs/npm/npmrc_username_no_password/install.out b/tests/specs/npm/npmrc_username_no_password/install.out
index d49a2ba0d8..b198bcd27e 100644
--- a/tests/specs/npm/npmrc_username_no_password/install.out
+++ b/tests/specs/npm/npmrc_username_no_password/install.out
@@ -1,3 +1,3 @@
 [UNORDERED_START]
-error: Error getting response at http://localhost:4261/@denotest/basic for package "@denotest/basic": Both the username and password must be provided for basic auth
+error: Error getting response at http://localhost:4261/@denotest%2fbasic for package "@denotest/basic": Both the username and password must be provided for basic auth
 [UNORDERED_END]
diff --git a/tests/specs/npm/npmrc_username_password/.npmrc b/tests/specs/npm/npmrc_username_password/.npmrc
index c318678aea..9e1ded96a3 100644
--- a/tests/specs/npm/npmrc_username_password/.npmrc
+++ b/tests/specs/npm/npmrc_username_password/.npmrc
@@ -1,6 +1,8 @@
 @denotest:registry=http://localhost:4261/
 //localhost:4261/:username=deno
-//localhost:4261/:_password=land
+# base64 of land
+//localhost:4261/:_password=bGFuZA==
 @denotest2:registry=http://localhost:4262/
 //localhost:4262/:username=deno
-//localhost:4262/:_password=land2
+# base64 of land2
+//localhost:4262/:_password=bGFuZDI=
diff --git a/tests/specs/npm/npmrc_username_password/install.out b/tests/specs/npm/npmrc_username_password/install.out
index 30643527e6..f2ea78c3f8 100644
--- a/tests/specs/npm/npmrc_username_password/install.out
+++ b/tests/specs/npm/npmrc_username_password/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4261/@denotest/basic
-Download http://localhost:4262/@denotest2/basic
+Download http://localhost:4261/@denotest%2fbasic
+Download http://localhost:4262/@denotest2%2fbasic
 Download http://localhost:4261/@denotest/basic/1.0.0.tgz
 Download http://localhost:4262/@denotest2/basic/1.0.0.tgz
 Initialize @denotest2/basic@1.0.0
diff --git a/tests/specs/npm/permissions_outside_package/permissions_outside_package/main.out b/tests/specs/npm/permissions_outside_package/permissions_outside_package/main.out
index 089f329c4f..0fde8cf87f 100644
--- a/tests/specs/npm/permissions_outside_package/permissions_outside_package/main.out
+++ b/tests/specs/npm/permissions_outside_package/permissions_outside_package/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/permissions-outside-package
+Download http://localhost:4260/@denotest%2fpermissions-outside-package
 Download http://localhost:4260/@denotest/permissions-outside-package/1.0.0.tgz
 { name: "foobar", version: "0.0.1" }
diff --git a/tests/specs/npm/require_resolve_bad_paths_global_cache/main.out b/tests/specs/npm/require_resolve_bad_paths_global_cache/main.out
index 3cc8a82794..2e82e68027 100644
--- a/tests/specs/npm/require_resolve_bad_paths_global_cache/main.out
+++ b/tests/specs/npm/require_resolve_bad_paths_global_cache/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/esm-basic
-Download http://localhost:4260/@denotest/require-resolve
+Download http://localhost:4260/@denotest%2fesm-basic
+Download http://localhost:4260/@denotest%2frequire-resolve
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
diff --git a/tests/specs/npm/require_type_commonjs/__test__.jsonc b/tests/specs/npm/require_type_commonjs/__test__.jsonc
index c9ba97ff52..a71173ce37 100644
--- a/tests/specs/npm/require_type_commonjs/__test__.jsonc
+++ b/tests/specs/npm/require_type_commonjs/__test__.jsonc
@@ -1,5 +1,4 @@
 {
   "args": "run --allow-read --quiet main.ts",
-  "output": "main.out",
-  "exitCode": 1
+  "output": "main.out"
 }
diff --git a/tests/specs/npm/require_type_commonjs/main.out b/tests/specs/npm/require_type_commonjs/main.out
index d715db8a94..00750edc07 100644
--- a/tests/specs/npm/require_type_commonjs/main.out
+++ b/tests/specs/npm/require_type_commonjs/main.out
@@ -1,4 +1 @@
-error: 'import', and 'export' cannot be used outside of module code at file://[WILDCARD]/@denotest/type-commonjs/1.0.0/index.js:1:1
-
-  export {};
-  ~~~~~~
+3
diff --git a/tests/specs/npm/require_type_commonjs/main.ts b/tests/specs/npm/require_type_commonjs/main.ts
index 243eb216e4..95ec6099ec 100644
--- a/tests/specs/npm/require_type_commonjs/main.ts
+++ b/tests/specs/npm/require_type_commonjs/main.ts
@@ -1 +1,2 @@
-import "npm:@denotest/type-commonjs";
+import { add } from "npm:@denotest/type-commonjs";
+console.log(add(1, 2));
diff --git a/tests/specs/npm/reserved_word_exports/reserved_word_exports/main.out b/tests/specs/npm/reserved_word_exports/reserved_word_exports/main.out
index ccfd35bc86..2a82194e37 100644
--- a/tests/specs/npm/reserved_word_exports/reserved_word_exports/main.out
+++ b/tests/specs/npm/reserved_word_exports/reserved_word_exports/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/reserved-word-exports
+Download http://localhost:4260/@denotest%2freserved-word-exports
 Download http://localhost:4260/@denotest/reserved-word-exports/1.0.0.tgz
 [Module: null prototype] {
   abstract: "abstract",
diff --git a/tests/specs/npm/run_existing_npm_package_with_subpath/run_existing_npm_package_with_subpath/main.out b/tests/specs/npm/run_existing_npm_package_with_subpath/run_existing_npm_package_with_subpath/main.out
index f6ee03ef1b..a473c32cc6 100644
--- a/tests/specs/npm/run_existing_npm_package_with_subpath/run_existing_npm_package_with_subpath/main.out
+++ b/tests/specs/npm/run_existing_npm_package_with_subpath/run_existing_npm_package_with_subpath/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/bin@1.0.0
 dev
diff --git a/tests/specs/npm/types_d_ext/d_ext/main.out b/tests/specs/npm/types_d_ext/d_ext/main.out
index e99df66965..5a834fbeb6 100644
--- a/tests/specs/npm/types_d_ext/d_ext/main.out
+++ b/tests/specs/npm/types_d_ext/d_ext/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/d-ext
+Download http://localhost:4260/@denotest%2fd-ext
 Download http://localhost:4260/@denotest/d-ext/1.0.0.tgz
 Check file:///[WILDCARD]/d_ext/main.ts
diff --git a/tests/specs/npm/types_entry_value_not_exists/types_entry_value_not_exists/main.out b/tests/specs/npm/types_entry_value_not_exists/types_entry_value_not_exists/main.out
index 017a17ea2e..62ef51d9f1 100644
--- a/tests/specs/npm/types_entry_value_not_exists/types_entry_value_not_exists/main.out
+++ b/tests/specs/npm/types_entry_value_not_exists/types_entry_value_not_exists/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/types-entry-value-not-exists
+Download http://localhost:4260/@denotest%2ftypes-entry-value-not-exists
 Download http://localhost:4260/@denotest/types-entry-value-not-exists/1.0.0.tgz
 Check file://[WILDCARD]/types_entry_value_not_exists/main.ts
 error: TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
diff --git a/tests/specs/npm/types_exports_import_types/types_exports_import_types/main.out b/tests/specs/npm/types_exports_import_types/types_exports_import_types/main.out
index 10f9425ca4..bb69bf86fb 100644
--- a/tests/specs/npm/types_exports_import_types/types_exports_import_types/main.out
+++ b/tests/specs/npm/types_exports_import_types/types_exports_import_types/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/types-exports-import-types
+Download http://localhost:4260/@denotest%2ftypes-exports-import-types
 Download http://localhost:4260/@denotest/types-exports-import-types/1.0.0.tgz
 Check file://[WILDCARD]/types_exports_import_types/main.ts
 error: TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
diff --git a/tests/specs/npm/types_general/main.out b/tests/specs/npm/types_general/main.out
index ffba4f84db..edc83f2a26 100644
--- a/tests/specs/npm/types_general/main.out
+++ b/tests/specs/npm/types_general/main.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/types
-Download http://localhost:4260/@denotest/types_imported
-Download http://localhost:4260/@denotest/types-exports-subpaths
+Download http://localhost:4260/@denotest%2ftypes
+Download http://localhost:4260/@denotest%2ftypes_imported
+Download http://localhost:4260/@denotest%2ftypes-exports-subpaths
 Download http://localhost:4260/@denotest/types_imported/1.0.0.tgz
 Download http://localhost:4260/@denotest/types-exports-subpaths/1.0.0.tgz
 Download http://localhost:4260/@denotest/types/1.0.0.tgz
diff --git a/tests/specs/npm/types_no_types_entry/types_no_types_entry/main.out b/tests/specs/npm/types_no_types_entry/types_no_types_entry/main.out
index 53e872eaf1..c867253ad9 100644
--- a/tests/specs/npm/types_no_types_entry/types_no_types_entry/main.out
+++ b/tests/specs/npm/types_no_types_entry/types_no_types_entry/main.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/types-no-types-entry
-Download http://localhost:4260/@denotest/types-entry-value-not-exists
+Download http://localhost:4260/@denotest%2ftypes-no-types-entry
+Download http://localhost:4260/@denotest%2ftypes-entry-value-not-exists
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/types-entry-value-not-exists/1.0.0.tgz
diff --git a/tests/specs/npm/typescript_file_in_package/__test__.jsonc b/tests/specs/npm/typescript_file_in_package/__test__.jsonc
index 08979ed257..7b5c5e1b67 100644
--- a/tests/specs/npm/typescript_file_in_package/__test__.jsonc
+++ b/tests/specs/npm/typescript_file_in_package/__test__.jsonc
@@ -1,5 +1,5 @@
 {
-  "args": "run typescript_file_in_package/main.ts",
-  "output": "typescript_file_in_package/main.out",
+  "args": "run main.ts",
+  "output": "main.out",
   "exitCode": 1
 }
diff --git a/tests/specs/npm/typescript_file_in_package/main.out b/tests/specs/npm/typescript_file_in_package/main.out
new file mode 100644
index 0000000000..58290a8737
--- /dev/null
+++ b/tests/specs/npm/typescript_file_in_package/main.out
@@ -0,0 +1,3 @@
+Download http://localhost:4260/@denotest%2ftypescript-file
+Download http://localhost:4260/@denotest/typescript-file/1.0.0.tgz
+error: TypeScript files are not supported in npm packages: file:///[WILDCARD]/@denotest/typescript-file/1.0.0/index.ts
diff --git a/tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.ts b/tests/specs/npm/typescript_file_in_package/main.ts
similarity index 100%
rename from tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.ts
rename to tests/specs/npm/typescript_file_in_package/main.ts
diff --git a/tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.out b/tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.out
deleted file mode 100644
index 3c3b971907..0000000000
--- a/tests/specs/npm/typescript_file_in_package/typescript_file_in_package/main.out
+++ /dev/null
@@ -1,6 +0,0 @@
-Download http://localhost:4260/@denotest/typescript-file
-Download http://localhost:4260/@denotest/typescript-file/1.0.0.tgz
-error: Could not resolve 'npm:@denotest/typescript-file@1.0.0'.
-
-Caused by:
-    TypeScript files are not supported in npm packages: file:///[WILDCARD]/@denotest/typescript-file/1.0.0/index.ts
diff --git a/tests/specs/npm/user_agent_env_var/__test__.jsonc b/tests/specs/npm/user_agent_env_var/__test__.jsonc
new file mode 100644
index 0000000000..a2af970a0e
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/__test__.jsonc
@@ -0,0 +1,46 @@
+{
+  "tempDir": true,
+  "tests": {
+    "set_for_npm_package": {
+      "steps": [
+        {
+          "args": "install",
+          "output": "[WILDCARD]"
+        },
+        {
+          "args": "run -A npm:@denotest/print-npm-user-agent",
+          "output": "run.out"
+        }
+      ]
+    },
+    "unset_for_local_file": {
+      "steps": [
+        {
+          "args": "run -A main.ts",
+          "output": "Download [WILDCARD]\nnpm_config_user_agent: undefined\n"
+        }
+      ]
+    },
+    "set_for_tasks": {
+      "steps": [
+        {
+          "args": "install",
+          "output": "[WILDCARD]"
+        },
+        {
+          "args": "task run-via-bin",
+          "output": "bin_command.out"
+        }
+      ]
+    },
+    "set_for_lifecycle_scripts": {
+      "steps": [
+        {
+          "args": "install --allow-scripts",
+          "output": "postinstall.out",
+          "exitCode": 1
+        }
+      ]
+    }
+  }
+}
diff --git a/tests/specs/npm/user_agent_env_var/bin_command.out b/tests/specs/npm/user_agent_env_var/bin_command.out
new file mode 100644
index 0000000000..c8e9413038
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/bin_command.out
@@ -0,0 +1,2 @@
+Task run-via-bin print-npm-user-agent
+npm_config_user_agent: deno/[WILDCARD] npm/? deno/[WILDCARD] [WILDCARD] [WILDCARD]
diff --git a/tests/specs/npm/user_agent_env_var/deno.jsonc b/tests/specs/npm/user_agent_env_var/deno.jsonc
new file mode 100644
index 0000000000..fbd70ec480
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/deno.jsonc
@@ -0,0 +1,3 @@
+{
+  "nodeModulesDir": "auto"
+}
diff --git a/tests/specs/npm/user_agent_env_var/main.ts b/tests/specs/npm/user_agent_env_var/main.ts
new file mode 100644
index 0000000000..2c51107e3c
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/main.ts
@@ -0,0 +1 @@
+console.log(`npm_config_user_agent: ${Deno.env.get("npm_config_user_agent")}`);
diff --git a/tests/specs/npm/user_agent_env_var/package.json b/tests/specs/npm/user_agent_env_var/package.json
new file mode 100644
index 0000000000..12cc0cc6fb
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/package.json
@@ -0,0 +1,8 @@
+{
+  "scripts": {
+    "run-via-bin": "print-npm-user-agent"
+  },
+  "dependencies": {
+    "@denotest/print-npm-user-agent": "1.0.0"
+  }
+}
diff --git a/tests/specs/npm/user_agent_env_var/postinstall.out b/tests/specs/npm/user_agent_env_var/postinstall.out
new file mode 100644
index 0000000000..19a08598fb
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/postinstall.out
@@ -0,0 +1,10 @@
+Download http://localhost:4260/@denotest%2fprint-npm-user-agent
+Download http://localhost:4260/@denotest/print-npm-user-agent/1.0.0.tgz
+Initialize @denotest/print-npm-user-agent@1.0.0
+Initialize @denotest/print-npm-user-agent@1.0.0: running 'postinstall' script
+error: script 'postinstall' in '@denotest/print-npm-user-agent@1.0.0' failed with exit code 1
+stdout:
+postinstall
+npm_config_user_agent: deno/[WILDCARD] npm/? deno/[WILDCARD] [WILDCARD] [WILDCARD]
+
+error: failed to run scripts for packages: @denotest/print-npm-user-agent@1.0.0
diff --git a/tests/specs/npm/user_agent_env_var/run.out b/tests/specs/npm/user_agent_env_var/run.out
new file mode 100644
index 0000000000..a630ac412f
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/run.out
@@ -0,0 +1 @@
+npm_config_user_agent: deno/[WILDCARD] npm/? deno/[WILDCARD] [WILDCARD] [WILDCARD]
diff --git a/tests/specs/npm/user_agent_env_var/test.mjs b/tests/specs/npm/user_agent_env_var/test.mjs
new file mode 100644
index 0000000000..ae035d40ef
--- /dev/null
+++ b/tests/specs/npm/user_agent_env_var/test.mjs
@@ -0,0 +1 @@
+console.log(process.env.npm_config_user_agent);
diff --git a/tests/specs/npm/workspace_basic/b/main_global_cache.out b/tests/specs/npm/workspace_basic/b/main_global_cache.out
index 203ac5a991..879f6ab050 100644
--- a/tests/specs/npm/workspace_basic/b/main_global_cache.out
+++ b/tests/specs/npm/workspace_basic/b/main_global_cache.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Hello 5
 Hello 5
diff --git a/tests/specs/npm/workspace_basic/b/main_node_modules_dir.out b/tests/specs/npm/workspace_basic/b/main_node_modules_dir.out
index eeb4556526..464c05c57c 100644
--- a/tests/specs/npm/workspace_basic/b/main_node_modules_dir.out
+++ b/tests/specs/npm/workspace_basic/b/main_node_modules_dir.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Hello 5
diff --git a/tests/specs/npm/workspace_basic/main.out b/tests/specs/npm/workspace_basic/main.out
index 92404af878..52d8267bb4 100644
--- a/tests/specs/npm/workspace_basic/main.out
+++ b/tests/specs/npm/workspace_basic/main.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Hello 5
 C: Hi!
diff --git a/tests/specs/permission/allow_import_worker/__test__.jsonc b/tests/specs/permission/allow_import_worker/__test__.jsonc
new file mode 100644
index 0000000000..21ac653033
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tests": {
+    "allowed": {
+      "args": "run -A --unstable-worker-options --quiet main.ts",
+      "output": "1\n"
+    },
+    "denied": {
+      "args": "run -A --unstable-worker-options --quiet main_denied.ts",
+      "output": "denied.out",
+      "exitCode": 1
+    }
+  }
+}
diff --git a/tests/specs/permission/allow_import_worker/denied.out b/tests/specs/permission/allow_import_worker/denied.out
new file mode 100644
index 0000000000..6e4dcaee09
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/denied.out
@@ -0,0 +1,7 @@
+error: Uncaught (in worker "") (in promise) TypeError: JSR package manifest for '@std/assert' failed to load. Requires import access to "127.0.0.1:4250", run again with the --allow-import flag
+await import(specifier);
+^
+    at async file:///[WILDLINE]
+error: Uncaught (in promise) Error: Unhandled error in child worker.
+    at [WILDLINE]
+    at [WILDLINE]
\ No newline at end of file
diff --git a/tests/specs/permission/allow_import_worker/main.ts b/tests/specs/permission/allow_import_worker/main.ts
new file mode 100644
index 0000000000..af65c40658
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/main.ts
@@ -0,0 +1,8 @@
+new Worker(import.meta.resolve("./worker.ts"), {
+  type: "module",
+  deno: {
+    permissions: {
+      import: ["127.0.0.1:4250"],
+    },
+  },
+});
diff --git a/tests/specs/permission/allow_import_worker/main_denied.ts b/tests/specs/permission/allow_import_worker/main_denied.ts
new file mode 100644
index 0000000000..e0d5a1d457
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/main_denied.ts
@@ -0,0 +1,8 @@
+new Worker(import.meta.resolve("./worker.ts"), {
+  type: "module",
+  deno: {
+    permissions: {
+      import: [],
+    },
+  },
+});
diff --git a/tests/specs/permission/allow_import_worker/worker.ts b/tests/specs/permission/allow_import_worker/worker.ts
new file mode 100644
index 0000000000..fd5757ba8d
--- /dev/null
+++ b/tests/specs/permission/allow_import_worker/worker.ts
@@ -0,0 +1,4 @@
+const specifier = "jsr:@std/assert/assert";
+await import(specifier);
+console.log(1);
+close();
diff --git a/tests/specs/publish/bare_node_builtins/bare_node_builtins.out b/tests/specs/publish/bare_node_builtins/bare_node_builtins.out
index 36ba9c7ce2..6baedd906f 100644
--- a/tests/specs/publish/bare_node_builtins/bare_node_builtins.out
+++ b/tests/specs/publish/bare_node_builtins/bare_node_builtins.out
@@ -1,7 +1,7 @@
 Warning Resolving "url" as "node:url" at file:///[WILDLINE]/mod.ts:1:22. If you want to use a built-in Node module, add a "node:" prefix.
 Warning Resolving "url" as "node:url" at file:///[WILDLINE]/mod.ts:1:22. If you want to use a built-in Node module, add a "node:" prefix.
 [UNORDERED_START]
-Download http://localhost:4260/@types/node
+Download http://localhost:4260/@types%2fnode
 Download http://localhost:4260/undici-types
 Download http://localhost:4260/@types/node/node-22.5.4.tgz
 Download http://localhost:4260/undici-types/undici-types-6.19.8.tgz
diff --git a/tests/specs/publish/missing_constraint/publish.out b/tests/specs/publish/missing_constraint/publish.out
index d9fb6408fb..7d2c293c0e 100644
--- a/tests/specs/publish/missing_constraint/publish.out
+++ b/tests/specs/publish/missing_constraint/publish.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
 Download http://127.0.0.1:4250/@denotest/add/meta.json
 Download http://127.0.0.1:4250/@denotest/deps/meta.json
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://127.0.0.1:4250/@denotest/add/1.0.0_meta.json
 Download http://127.0.0.1:4250/@denotest/deps/1.0.0_meta.json
 Download http://127.0.0.1:4250/@denotest/module-graph/meta.json
diff --git a/tests/specs/publish/node_specifier/node_specifier.out b/tests/specs/publish/node_specifier/node_specifier.out
index 4c9d7cb3e2..0ba14043df 100644
--- a/tests/specs/publish/node_specifier/node_specifier.out
+++ b/tests/specs/publish/node_specifier/node_specifier.out
@@ -1,5 +1,5 @@
 [UNORDERED_START]
-Download http://localhost:4260/@types/node
+Download http://localhost:4260/@types%2fnode
 Download http://localhost:4260/undici-types
 Download http://localhost:4260/@types/node/node-22.5.4.tgz
 Download http://localhost:4260/undici-types/undici-types-6.19.8.tgz
diff --git a/tests/specs/remove/alias/__test__.jsonc b/tests/specs/remove/alias/__test__.jsonc
new file mode 100644
index 0000000000..a0c98edd90
--- /dev/null
+++ b/tests/specs/remove/alias/__test__.jsonc
@@ -0,0 +1,29 @@
+{
+  "tempDir": true,
+  "tests": {
+    "alias_with_pkg": {
+      "steps": [{
+        "args": "remove my-alias@npm:@denotest/add",
+        "output": "[WILDCARD]"
+      }, {
+        "args": [
+          "eval",
+          "console.log(Deno.readTextFileSync('package.json').trim())"
+        ],
+        "output": "package.json.out"
+      }]
+    },
+    "alias": {
+      "steps": [{
+        "args": "remove my-alias",
+        "output": "[WILDCARD]"
+      }, {
+        "args": [
+          "eval",
+          "console.log(Deno.readTextFileSync('package.json').trim())"
+        ],
+        "output": "package.json.out"
+      }]
+    }
+  }
+}
diff --git a/tests/specs/remove/alias/package.json b/tests/specs/remove/alias/package.json
new file mode 100644
index 0000000000..b6326e8bfb
--- /dev/null
+++ b/tests/specs/remove/alias/package.json
@@ -0,0 +1,5 @@
+{
+  "dependencies": {
+    "my-alias": "npm:@denotest/add@^1.0.0"
+  }
+}
diff --git a/tests/specs/remove/alias/package.json.out b/tests/specs/remove/alias/package.json.out
new file mode 100644
index 0000000000..2c63c08510
--- /dev/null
+++ b/tests/specs/remove/alias/package.json.out
@@ -0,0 +1,2 @@
+{
+}
diff --git a/tests/specs/remove/basic/__test__.jsonc b/tests/specs/remove/basic/__test__.jsonc
index fd74900b44..3ca396f8ba 100644
--- a/tests/specs/remove/basic/__test__.jsonc
+++ b/tests/specs/remove/basic/__test__.jsonc
@@ -7,7 +7,7 @@
     "args": ["eval", "console.log(Deno.readTextFileSync('deno.lock').trim())"],
     "output": "add_lock.out"
   }, {
-    "args": ["remove", "@std/assert", "@std/http"],
+    "args": ["remove", "jsr:@std/assert", "@std/http"],
     "output": "rm.out"
   }, {
     "args": ["eval", "console.log(Deno.readTextFileSync('deno.lock').trim())"],
diff --git a/tests/specs/remove/package_json/rm_add.out b/tests/specs/remove/package_json/rm_add.out
index b98c27bae6..af72f5f99d 100644
--- a/tests/specs/remove/package_json/rm_add.out
+++ b/tests/specs/remove/package_json/rm_add.out
@@ -1,4 +1,4 @@
 Removed @denotest/add
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/repl/console_log/093_console_log_format.js b/tests/specs/repl/console_log/093_console_log_format.js
new file mode 100644
index 0000000000..15022411ca
--- /dev/null
+++ b/tests/specs/repl/console_log/093_console_log_format.js
@@ -0,0 +1,16 @@
+// Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
+class Frac {
+  constructor(num, den) {
+    this.num = num;
+    this.den = den;
+  }
+  [Symbol.toPrimitive]() {
+    return this.num / this.den;
+  }
+  display() {
+    const result = this.num / this.den;
+    process.stdout.write(`${result}`);
+  }
+}
+const f = new Frac(1, 2);
+f.display();
diff --git a/tests/specs/repl/console_log/093_console_log_format.out b/tests/specs/repl/console_log/093_console_log_format.out
new file mode 100644
index 0000000000..ea2303bc03
--- /dev/null
+++ b/tests/specs/repl/console_log/093_console_log_format.out
@@ -0,0 +1 @@
+0.5
\ No newline at end of file
diff --git a/tests/specs/repl/console_log/__test__.jsonc b/tests/specs/repl/console_log/__test__.jsonc
new file mode 100644
index 0000000000..641bc1f68a
--- /dev/null
+++ b/tests/specs/repl/console_log/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run -A --quiet 093_console_log_format.js",
+  "output": "093_console_log_format.out"
+}
diff --git a/tests/specs/run/cjs/main_module/__test__.jsonc b/tests/specs/run/cjs/main_module/__test__.jsonc
new file mode 100644
index 0000000000..e756a63627
--- /dev/null
+++ b/tests/specs/run/cjs/main_module/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read main.cjs",
+  "output": "main.out"
+}
diff --git a/tests/specs/run/cjs/main_module/main.cjs b/tests/specs/run/cjs/main_module/main.cjs
new file mode 100644
index 0000000000..2a4c57ab1c
--- /dev/null
+++ b/tests/specs/run/cjs/main_module/main.cjs
@@ -0,0 +1 @@
+console.log(require.main);
diff --git a/tests/specs/run/cjs/main_module/main.out b/tests/specs/run/cjs/main_module/main.out
new file mode 100644
index 0000000000..93b86d27e3
--- /dev/null
+++ b/tests/specs/run/cjs/main_module/main.out
@@ -0,0 +1,5 @@
+Module {
+  id: ".",
+  [WILDCARD]
+  filename: "[WILDCARD]main.cjs",
+[WILDCARD]
\ No newline at end of file
diff --git a/tests/specs/run/cjs_reexport_non_analyzable/__test__.jsonc b/tests/specs/run/cjs/reexport_non_analyzable/__test__.jsonc
similarity index 100%
rename from tests/specs/run/cjs_reexport_non_analyzable/__test__.jsonc
rename to tests/specs/run/cjs/reexport_non_analyzable/__test__.jsonc
diff --git a/tests/specs/run/cjs_reexport_non_analyzable/deno.json b/tests/specs/run/cjs/reexport_non_analyzable/deno.json
similarity index 100%
rename from tests/specs/run/cjs_reexport_non_analyzable/deno.json
rename to tests/specs/run/cjs/reexport_non_analyzable/deno.json
diff --git a/tests/specs/run/cjs_reexport_non_analyzable/main.ts b/tests/specs/run/cjs/reexport_non_analyzable/main.ts
similarity index 100%
rename from tests/specs/run/cjs_reexport_non_analyzable/main.ts
rename to tests/specs/run/cjs/reexport_non_analyzable/main.ts
diff --git a/tests/specs/run/cjs_reexport_non_analyzable/node_modules/foo.cjs b/tests/specs/run/cjs/reexport_non_analyzable/node_modules/foo.cjs
similarity index 100%
rename from tests/specs/run/cjs_reexport_non_analyzable/node_modules/foo.cjs
rename to tests/specs/run/cjs/reexport_non_analyzable/node_modules/foo.cjs
diff --git a/tests/specs/run/cjs/unprepared/__test__.jsonc b/tests/specs/run/cjs/unprepared/__test__.jsonc
new file mode 100644
index 0000000000..f816bad869
--- /dev/null
+++ b/tests/specs/run/cjs/unprepared/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run -A main.ts",
+  "output": "main.out"
+}
diff --git a/tests/specs/run/cjs/unprepared/file.cjs b/tests/specs/run/cjs/unprepared/file.cjs
new file mode 100644
index 0000000000..ba0c6fa6ff
--- /dev/null
+++ b/tests/specs/run/cjs/unprepared/file.cjs
@@ -0,0 +1,7 @@
+// non-analyzable
+const moduleName = "./output.cjs";
+function getModuleName() {
+  return moduleName;
+}
+
+require(getModuleName());
diff --git a/tests/specs/run/cjs/unprepared/main.out b/tests/specs/run/cjs/unprepared/main.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/run/cjs/unprepared/main.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/run/cjs/unprepared/main.ts b/tests/specs/run/cjs/unprepared/main.ts
new file mode 100644
index 0000000000..5630b4fbc3
--- /dev/null
+++ b/tests/specs/run/cjs/unprepared/main.ts
@@ -0,0 +1,7 @@
+// non-analyzable
+const moduleName = "./output.cjs";
+function getModuleName() {
+  return moduleName;
+}
+
+await import(getModuleName());
diff --git a/tests/specs/run/cjs/unprepared/output.cjs b/tests/specs/run/cjs/unprepared/output.cjs
new file mode 100644
index 0000000000..54ed3702f5
--- /dev/null
+++ b/tests/specs/run/cjs/unprepared/output.cjs
@@ -0,0 +1,3 @@
+console.log("Hello");
+
+module.exports = 1;
diff --git a/tests/specs/run/cts/cjs_import_cts/__test__.jsonc b/tests/specs/run/cts/cjs_import_cts/__test__.jsonc
new file mode 100644
index 0000000000..2205183d07
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tests": {
+    "no_check": {
+      "args": "run --allow-read main.js",
+      "output": "main.out"
+    },
+    "check": {
+      "args": "check main.js",
+      "output": "check.out",
+      "exitCode": 1
+    }
+  }
+}
diff --git a/tests/specs/run/cts/cjs_import_cts/add.cts b/tests/specs/run/cts/cjs_import_cts/add.cts
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/add.cts
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/cts/cjs_import_cts/check.out b/tests/specs/run/cts/cjs_import_cts/check.out
new file mode 100644
index 0000000000..a27e8d7af7
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/check.out
@@ -0,0 +1,17 @@
+Check file:///[WILDLINE]main.js
+error: TS2580 [ERROR]: Cannot find name 'module'.
+module.exports.add = function (a, b) {
+~~~~~~
+    at file:///[WILDLINE]
+
+TS7006 [ERROR]: Parameter 'a' implicitly has an 'any' type.
+module.exports.add = function (a, b) {
+                               ^
+    at file:///[WILDLINE]
+
+TS7006 [ERROR]: Parameter 'b' implicitly has an 'any' type.
+module.exports.add = function (a, b) {
+                                  ^
+    at file:///[WILDLINE]
+
+Found 3 errors.
diff --git a/tests/specs/run/cts/cjs_import_cts/main.js b/tests/specs/run/cts/cjs_import_cts/main.js
new file mode 100644
index 0000000000..9546a0fea5
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/main.js
@@ -0,0 +1,3 @@
+import { subtract } from "./subtract.cjs";
+
+console.log(subtract(1, 2));
diff --git a/tests/specs/run/cts/cjs_import_cts/main.out b/tests/specs/run/cts/cjs_import_cts/main.out
new file mode 100644
index 0000000000..3a2e3f4984
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/main.out
@@ -0,0 +1 @@
+-1
diff --git a/tests/specs/run/cts/cjs_import_cts/subtract.cjs b/tests/specs/run/cts/cjs_import_cts/subtract.cjs
new file mode 100644
index 0000000000..7dee54346f
--- /dev/null
+++ b/tests/specs/run/cts/cjs_import_cts/subtract.cjs
@@ -0,0 +1,3 @@
+module.exports.subtract = function (a, b) {
+  return require("./add.cts").add(a, -b);
+};
diff --git a/tests/specs/run/cts/import_export_equals/__test__.jsonc b/tests/specs/run/cts/import_export_equals/__test__.jsonc
new file mode 100644
index 0000000000..6a5c6db420
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/__test__.jsonc
@@ -0,0 +1,17 @@
+{
+  "tests": {
+    "main": {
+      "args": "run --check --allow-read=. main.cts",
+      "output": "main.out"
+    },
+    "mts": {
+      "args": "run --allow-read=. mod.mts",
+      "output": "mod.mts.out"
+    },
+    "mts_check": {
+      "args": "check mod.mts",
+      "output": "mod.mts.check.out",
+      "exitCode": 1
+    }
+  }
+}
diff --git a/tests/specs/run/cts/import_export_equals/add.cts b/tests/specs/run/cts/import_export_equals/add.cts
new file mode 100644
index 0000000000..adf3503ac5
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/add.cts
@@ -0,0 +1,3 @@
+export = function (a: number, b: number) {
+  return a + b;
+};
diff --git a/tests/specs/run/cts/import_export_equals/main.cts b/tests/specs/run/cts/import_export_equals/main.cts
new file mode 100644
index 0000000000..e5c45f92e0
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/main.cts
@@ -0,0 +1,3 @@
+import add = require("./add.cts");
+
+console.log(add(1, 2));
diff --git a/tests/specs/run/cts/import_export_equals/main.out b/tests/specs/run/cts/import_export_equals/main.out
new file mode 100644
index 0000000000..e7a973a7d0
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/main.out
@@ -0,0 +1,2 @@
+Check file:///[WILDLINE]/main.cts
+3
diff --git a/tests/specs/run/cts/import_export_equals/mod.mts b/tests/specs/run/cts/import_export_equals/mod.mts
new file mode 100644
index 0000000000..5fbbd6c6a0
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/mod.mts
@@ -0,0 +1,3 @@
+import add from "./add.cts";
+
+console.log(add(1, "test"));
diff --git a/tests/specs/run/cts/import_export_equals/mod.mts.check.out b/tests/specs/run/cts/import_export_equals/mod.mts.check.out
new file mode 100644
index 0000000000..8703539019
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/mod.mts.check.out
@@ -0,0 +1,5 @@
+Check file:///[WILDLINE]/mod.mts
+error: TS2345 [ERROR]: Argument of type 'string' is not assignable to parameter of type 'number'.
+console.log(add(1, "test"));
+                   ~~~~~~
+    at file:///[WILDLINE]/mod.mts:3:20
diff --git a/tests/specs/run/cts/import_export_equals/mod.mts.out b/tests/specs/run/cts/import_export_equals/mod.mts.out
new file mode 100644
index 0000000000..208465a080
--- /dev/null
+++ b/tests/specs/run/cts/import_export_equals/mod.mts.out
@@ -0,0 +1 @@
+1test
diff --git a/tests/specs/run/cts/main/__test__.jsonc b/tests/specs/run/cts/main/__test__.jsonc
new file mode 100644
index 0000000000..0157b44e96
--- /dev/null
+++ b/tests/specs/run/cts/main/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read main.cts",
+  "output": "main.out"
+}
diff --git a/tests/specs/run/cts/main/import_main.cjs b/tests/specs/run/cts/main/import_main.cjs
new file mode 100644
index 0000000000..f61e0da2a6
--- /dev/null
+++ b/tests/specs/run/cts/main/import_main.cjs
@@ -0,0 +1 @@
+require("./main.cts").sayHello();
diff --git a/tests/specs/run/cts/main/main.cts b/tests/specs/run/cts/main/main.cts
new file mode 100644
index 0000000000..0b0330686b
--- /dev/null
+++ b/tests/specs/run/cts/main/main.cts
@@ -0,0 +1,5 @@
+module.exports.sayHello = function () {
+  console.log("Hello");
+};
+
+require("./import_main.cjs");
diff --git a/tests/specs/run/cts/main/main.out b/tests/specs/run/cts/main/main.out
new file mode 100644
index 0000000000..e965047ad7
--- /dev/null
+++ b/tests/specs/run/cts/main/main.out
@@ -0,0 +1 @@
+Hello
diff --git a/tests/specs/run/document/__test__.jsonc b/tests/specs/run/document/__test__.jsonc
new file mode 100644
index 0000000000..cf20f9e1b2
--- /dev/null
+++ b/tests/specs/run/document/__test__.jsonc
@@ -0,0 +1,9 @@
+{
+  "tests": {
+    "document": {
+      "args": "run document.js",
+      "exitCode": 1,
+      "output": "document.out"
+    }
+  }
+}
diff --git a/tests/specs/run/document/document.js b/tests/specs/run/document/document.js
new file mode 100644
index 0000000000..63e43b72f0
--- /dev/null
+++ b/tests/specs/run/document/document.js
@@ -0,0 +1 @@
+document.querySelector("div");
diff --git a/tests/specs/run/document/document.out b/tests/specs/run/document/document.out
new file mode 100644
index 0000000000..eefedb8f2b
--- /dev/null
+++ b/tests/specs/run/document/document.out
@@ -0,0 +1,8 @@
+error: Uncaught (in promise) ReferenceError: document is not defined
+document.querySelector("div");
+^
+    at [WILDCARD]document.js:1:1
+
+    info: document global is not available in Deno.
+    hint: Use a library like happy-dom, deno_dom, linkedom or JSDom
+          and setup the document global according to the library documentation.
diff --git a/tests/specs/run/import_common_js/__test__.jsonc b/tests/specs/run/import_common_js/__test__.jsonc
index 950c7f68c3..6510dbad7b 100644
--- a/tests/specs/run/import_common_js/__test__.jsonc
+++ b/tests/specs/run/import_common_js/__test__.jsonc
@@ -11,6 +11,11 @@
       "args": "run exports_error.js",
       "output": "exports_error.out",
       "exitCode": 1
+    },
+    {
+      "args": "run require_error.js",
+      "output": "require_error.out",
+      "exitCode": 1
     }
   ]
 }
diff --git a/tests/specs/run/import_common_js/exports_error.out b/tests/specs/run/import_common_js/exports_error.out
index 41eda24575..b979cce5c7 100644
--- a/tests/specs/run/import_common_js/exports_error.out
+++ b/tests/specs/run/import_common_js/exports_error.out
@@ -3,5 +3,10 @@ Object.defineProperty(exports, "__esModule", { value: true });
                       ^
     at [WILDCARD]exports_error.js:1:23
 
-    info: Deno does not support CommonJS modules without `.cjs` extension.
-    hint: Rewrite this module to ESM or change the file extension to `.cjs`.
+    info: Deno supports CommonJS modules in .cjs files, or when there's a package.json
+          with "type": "commonjs" option and --unstable-detect-cjs flag is used.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option
+          and pass --unstable-detect-cjs flag.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/import_common_js/module_error.out b/tests/specs/run/import_common_js/module_error.out
index 53a908d291..654ee838dd 100644
--- a/tests/specs/run/import_common_js/module_error.out
+++ b/tests/specs/run/import_common_js/module_error.out
@@ -3,5 +3,10 @@ module.exports = {
 ^
     at [WILDCARD]module_error.js:1:1
 
-    info: Deno does not support CommonJS modules without `.cjs` extension.
-    hint: Rewrite this module to ESM or change the file extension to `.cjs`.
+    info: Deno supports CommonJS modules in .cjs files, or when there's a package.json
+          with "type": "commonjs" option and --unstable-detect-cjs flag is used.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option
+          and pass --unstable-detect-cjs flag.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/import_common_js/require_error.js b/tests/specs/run/import_common_js/require_error.js
new file mode 100644
index 0000000000..9567689331
--- /dev/null
+++ b/tests/specs/run/import_common_js/require_error.js
@@ -0,0 +1,2 @@
+const process = require("process");
+const a = require("./a");
diff --git a/tests/specs/run/import_common_js/require_error.out b/tests/specs/run/import_common_js/require_error.out
new file mode 100644
index 0000000000..81ffd6591f
--- /dev/null
+++ b/tests/specs/run/import_common_js/require_error.out
@@ -0,0 +1,12 @@
+error: Uncaught (in promise) ReferenceError: require is not defined
+const process = require("process");
+                ^
+    at [WILDCARD]require_error.js:1:17
+
+    info: Deno supports CommonJS modules in .cjs files, or when there's a package.json
+          with "type": "commonjs" option and --unstable-detect-cjs flag is used.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option
+          and pass --unstable-detect-cjs flag.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/no_deno_json/code/install.out b/tests/specs/run/no_deno_json/code/install.out
index 321dc8ebcb..ddaf104c3b 100644
--- a/tests/specs/run/no_deno_json/code/install.out
+++ b/tests/specs/run/no_deno_json/code/install.out
@@ -1,6 +1,6 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/check-error
-Download http://localhost:4260/@denotest/cjs-default-export
+Download http://localhost:4260/@denotest%2fcheck-error
+Download http://localhost:4260/@denotest%2fcjs-default-export
 Download http://localhost:4260/chalk
 Download http://localhost:4260/ansi-styles
 Download http://localhost:4260/supports-color
diff --git a/tests/specs/run/node_globals_hints/__test__.jsonc b/tests/specs/run/node_globals_hints/__test__.jsonc
new file mode 100644
index 0000000000..c5c5d6e42e
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/__test__.jsonc
@@ -0,0 +1,34 @@
+{
+  "tests": {
+    "__dirname": {
+      "args": "run dirname.js",
+      "output": "dirname.out",
+      "exitCode": 1
+    },
+    "__filename": {
+      "args": "run filename.js",
+      "output": "filename.out",
+      "exitCode": 1
+    },
+    "clearImmediate": {
+      "args": "run clear_immediate.js",
+      "output": "clear_immediate.out",
+      "exitCode": 1
+    },
+    "buffer": {
+      "args": "run buffer.js",
+      "output": "buffer.out",
+      "exitCode": 1
+    },
+    "global": {
+      "args": "run global.js",
+      "output": "global.out",
+      "exitCode": 1
+    },
+    "setImmediate": {
+      "args": "run set_immediate.js",
+      "output": "set_immediate.out",
+      "exitCode": 1
+    }
+  }
+}
diff --git a/tests/specs/run/node_globals_hints/buffer.js b/tests/specs/run/node_globals_hints/buffer.js
new file mode 100644
index 0000000000..9809e1656e
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/buffer.js
@@ -0,0 +1 @@
+Buffer;
diff --git a/tests/specs/run/node_globals_hints/buffer.out b/tests/specs/run/node_globals_hints/buffer.out
new file mode 100644
index 0000000000..4980e6d129
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/buffer.out
@@ -0,0 +1,7 @@
+error: Uncaught (in promise) ReferenceError: Buffer is not defined
+Buffer;
+^
+    at [WILDCARD]buffer.js:1:1
+
+    info: Buffer is not available in the global scope in Deno.
+    hint: Import it explicitly with import { Buffer } from "node:buffer";.
diff --git a/tests/specs/run/node_globals_hints/clear_immediate.js b/tests/specs/run/node_globals_hints/clear_immediate.js
new file mode 100644
index 0000000000..94b26ae682
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/clear_immediate.js
@@ -0,0 +1 @@
+clearImmediate;
diff --git a/tests/specs/run/node_globals_hints/clear_immediate.out b/tests/specs/run/node_globals_hints/clear_immediate.out
new file mode 100644
index 0000000000..ecd34babef
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/clear_immediate.out
@@ -0,0 +1,7 @@
+error: Uncaught (in promise) ReferenceError: clearImmediate is not defined
+clearImmediate;
+^
+    at [WILDCARD]clear_immediate.js:1:1
+
+    info: clearImmediate is not available in the global scope in Deno.
+    hint: Import it explicitly with import { clearImmediate } from "node:timers";.
diff --git a/tests/specs/run/node_globals_hints/dirname.js b/tests/specs/run/node_globals_hints/dirname.js
new file mode 100644
index 0000000000..58d9e93794
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/dirname.js
@@ -0,0 +1 @@
+__dirname;
diff --git a/tests/specs/run/node_globals_hints/dirname.out b/tests/specs/run/node_globals_hints/dirname.out
new file mode 100644
index 0000000000..0aa3e4f51b
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/dirname.out
@@ -0,0 +1,7 @@
+error: Uncaught (in promise) ReferenceError: __dirname is not defined
+__dirname;
+^
+    at [WILDCARD]dirname.js:1:1
+
+    info: __dirname global is not available in ES modules.
+    hint: Use import.meta.dirname instead.
diff --git a/tests/specs/run/node_globals_hints/filename.js b/tests/specs/run/node_globals_hints/filename.js
new file mode 100644
index 0000000000..31770bb141
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/filename.js
@@ -0,0 +1 @@
+__filename;
diff --git a/tests/specs/run/node_globals_hints/filename.out b/tests/specs/run/node_globals_hints/filename.out
new file mode 100644
index 0000000000..47b4264fbd
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/filename.out
@@ -0,0 +1,7 @@
+error: Uncaught (in promise) ReferenceError: __filename is not defined
+__filename;
+^
+    at [WILDCARD]filename.js:1:1
+
+    info: __filename global is not available in ES modules.
+    hint: Use import.meta.filename instead.
diff --git a/tests/specs/run/node_globals_hints/global.js b/tests/specs/run/node_globals_hints/global.js
new file mode 100644
index 0000000000..56676d726a
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/global.js
@@ -0,0 +1 @@
+global;
diff --git a/tests/specs/run/node_globals_hints/global.out b/tests/specs/run/node_globals_hints/global.out
new file mode 100644
index 0000000000..e090d32e29
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/global.out
@@ -0,0 +1,7 @@
+error: Uncaught (in promise) ReferenceError: global is not defined
+global;
+^
+    at [WILDCARD]global.js:1:1
+
+    info: global is not available in the global scope in Deno.
+    hint: Use globalThis instead, or assign globalThis.global = globalThis.
diff --git a/tests/specs/run/node_globals_hints/set_immediate.js b/tests/specs/run/node_globals_hints/set_immediate.js
new file mode 100644
index 0000000000..fa29d1e714
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/set_immediate.js
@@ -0,0 +1 @@
+setImmediate;
diff --git a/tests/specs/run/node_globals_hints/set_immediate.out b/tests/specs/run/node_globals_hints/set_immediate.out
new file mode 100644
index 0000000000..38859ff5d7
--- /dev/null
+++ b/tests/specs/run/node_globals_hints/set_immediate.out
@@ -0,0 +1,7 @@
+error: Uncaught (in promise) ReferenceError: setImmediate is not defined
+setImmediate;
+^
+    at [WILDCARD]set_immediate.js:1:1
+
+    info: setImmediate is not available in the global scope in Deno.
+    hint: Import it explicitly with import { setImmediate } from "node:timers";.
diff --git a/tests/specs/run/package_json/invalid_value/add.out b/tests/specs/run/package_json/invalid_value/add.out
index 9b7493c1a2..32d9acaed6 100644
--- a/tests/specs/run/package_json/invalid_value/add.out
+++ b/tests/specs/run/package_json/invalid_value/add.out
@@ -1,5 +1,6 @@
 Add npm:cowsay@1.5.0
-error: Failed to install from package.json
+error: Failed to install '@denotest/cjs-default-export'
+    at file:///[WILDLINE]/package.json
 
 Caused by:
     0: Invalid version requirement
diff --git a/tests/specs/run/package_json/invalid_value/error_auto.out b/tests/specs/run/package_json/invalid_value/error_auto.out
index 7641a4d863..966375a3df 100644
--- a/tests/specs/run/package_json/invalid_value/error_auto.out
+++ b/tests/specs/run/package_json/invalid_value/error_auto.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 error: Invalid version requirement
diff --git a/tests/specs/run/package_json/invalid_value/install.out b/tests/specs/run/package_json/invalid_value/install.out
index cc82b345b0..ca3492ab22 100644
--- a/tests/specs/run/package_json/invalid_value/install.out
+++ b/tests/specs/run/package_json/invalid_value/install.out
@@ -1,4 +1,5 @@
-error: Failed to install from package.json
+error: Failed to install '@denotest/cjs-default-export'
+    at file:///[WILDLINE]/package.json
 
 Caused by:
     0: Invalid version requirement
diff --git a/tests/specs/run/package_json/invalid_value/task.out b/tests/specs/run/package_json/invalid_value/task.out
index d0adb05256..2f9580fa61 100644
--- a/tests/specs/run/package_json/invalid_value/task.out
+++ b/tests/specs/run/package_json/invalid_value/task.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Task test echo 1
diff --git a/tests/specs/run/package_json_type/commonjs/basic/__test__.jsonc b/tests/specs/run/package_json_type/commonjs/basic/__test__.jsonc
new file mode 100644
index 0000000000..85b7219fa0
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/__test__.jsonc
@@ -0,0 +1,34 @@
+{
+  "tests": {
+    "main_cjs": {
+      "args": "run --allow-read=. main_cjs.js",
+      "output": "3\n"
+    },
+    "main_esm": {
+      "args": "run --allow-read=. main_esm.js",
+      "output": "3\n"
+    },
+    "main_mix": {
+      "args": "run --allow-read=. main_mix.js",
+      "output": "main_mix.out",
+      "exitCode": 1
+    },
+    "import_import_meta": {
+      "args": "run import_import_meta.js",
+      "output": "[WILDLINE]/import_meta.js\n"
+    },
+    "main_import_meta": {
+      "args": "run main_esm_import_meta.js",
+      "output": "main_esm_import_meta.out",
+      "exitCode": 1
+    },
+    "not_import_meta": {
+      "args": "run --allow-read=. not_import_meta.js",
+      "output": "3\n"
+    },
+    "tla": {
+      "args": "run --allow-read=. tla.js",
+      "output": "loaded\n"
+    }
+  }
+}
diff --git a/tests/specs/run/package_json_type/commonjs/basic/add.js b/tests/specs/run/package_json_type/commonjs/basic/add.js
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/package_json_type/commonjs/basic/deno.jsonc b/tests/specs/run/package_json_type/commonjs/basic/deno.jsonc
new file mode 100644
index 0000000000..35f64c86f4
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/deno.jsonc
@@ -0,0 +1,5 @@
+{
+  "unstable": [
+    "detect-cjs"
+  ]
+}
diff --git a/tests/specs/run/package_json_type/commonjs/basic/import_import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/import_import_meta.js
new file mode 100644
index 0000000000..f07518985a
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/import_import_meta.js
@@ -0,0 +1,3 @@
+import { value } from "./import_meta.js";
+
+console.log(value);
diff --git a/tests/specs/run/package_json_type/commonjs/basic/import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/import_meta.js
new file mode 100644
index 0000000000..2bdbc30fe6
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/import_meta.js
@@ -0,0 +1 @@
+export const value = import.meta.url;
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_cjs.js b/tests/specs/run/package_json_type/commonjs/basic/main_cjs.js
new file mode 100644
index 0000000000..365e8e06f8
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_cjs.js
@@ -0,0 +1,2 @@
+const { add } = require("./add");
+console.log(add(1, 2));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_esm.js b/tests/specs/run/package_json_type/commonjs/basic/main_esm.js
new file mode 100644
index 0000000000..8c55f673b0
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_esm.js
@@ -0,0 +1,3 @@
+import { add } from "./add.js";
+
+console.log(add(1, 2));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.js
new file mode 100644
index 0000000000..f1dff20b57
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.js
@@ -0,0 +1,2 @@
+console.log(import.meta.url);
+console.log(require("./add"));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.out b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.out
new file mode 100644
index 0000000000..e177defffd
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_esm_import_meta.out
@@ -0,0 +1,2 @@
+[WILDLINE]main_esm_import_meta.js
+error: Uncaught (in promise) ReferenceError: require is not defined[WILDCARD]
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_mix.js b/tests/specs/run/package_json_type/commonjs/basic/main_mix.js
new file mode 100644
index 0000000000..2a2c2c62a2
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_mix.js
@@ -0,0 +1,6 @@
+import { add } from "./add.js";
+
+console.log(add(1, 2));
+
+// will error
+console.log(require("./add").add(1, 2));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/main_mix.out b/tests/specs/run/package_json_type/commonjs/basic/main_mix.out
new file mode 100644
index 0000000000..78f421644c
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/main_mix.out
@@ -0,0 +1,13 @@
+3
+error: Uncaught (in promise) ReferenceError: require is not defined
+console.log(require("./add").add(1, 2));
+        ^
+    at file:///[WILDLINE]main_mix.js:[WILDLINE]
+
+    info: Deno supports CommonJS modules in .cjs files, or when there's a package.json
+          with "type": "commonjs" option and --unstable-detect-cjs flag is used.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option
+          and pass --unstable-detect-cjs flag.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/package_json_type/commonjs/basic/not_import_meta.js b/tests/specs/run/package_json_type/commonjs/basic/not_import_meta.js
new file mode 100644
index 0000000000..216b900df6
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/not_import_meta.js
@@ -0,0 +1,8 @@
+try {
+  console.log(test.import.meta.url);
+} catch {
+  // ignore
+}
+
+// should work because this is not an ESM file
+console.log(require("./add").add(1, 2));
diff --git a/tests/specs/run/package_json_type/commonjs/basic/package.json b/tests/specs/run/package_json_type/commonjs/basic/package.json
new file mode 100644
index 0000000000..5bbefffbab
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/package.json
@@ -0,0 +1,3 @@
+{
+  "type": "commonjs"
+}
diff --git a/tests/specs/run/package_json_type/commonjs/basic/tla.js b/tests/specs/run/package_json_type/commonjs/basic/tla.js
new file mode 100644
index 0000000000..978578de46
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/basic/tla.js
@@ -0,0 +1,2 @@
+await new Promise((r) => r());
+console.log("loaded");
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/__test__.jsonc b/tests/specs/run/package_json_type/commonjs/jsx/__test__.jsonc
new file mode 100644
index 0000000000..f815fd72cb
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "tempDir": true,
+  "args": "run -A --quiet main.jsx",
+  "output": "main.out"
+}
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/add.js b/tests/specs/run/package_json_type/commonjs/jsx/add.js
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/deno.jsonc b/tests/specs/run/package_json_type/commonjs/jsx/deno.jsonc
new file mode 100644
index 0000000000..192ddb98c4
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/deno.jsonc
@@ -0,0 +1,10 @@
+{
+  "nodeModulesDir": "auto",
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "react"
+  },
+  "unstable": [
+    "detect-cjs"
+  ]
+}
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/main.jsx b/tests/specs/run/package_json_type/commonjs/jsx/main.jsx
new file mode 100644
index 0000000000..1922fce1bb
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/main.jsx
@@ -0,0 +1,7 @@
+const { add } = require("./add.js");
+
+console.log(add(1, 2));
+
+console.log(<div /> != null);
+
+require("./tsx.tsx");
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/main.out b/tests/specs/run/package_json_type/commonjs/jsx/main.out
new file mode 100644
index 0000000000..cdcf045418
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/main.out
@@ -0,0 +1,4 @@
+3
+true
+4
+true
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/package.json b/tests/specs/run/package_json_type/commonjs/jsx/package.json
new file mode 100644
index 0000000000..88afcdcd95
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/package.json
@@ -0,0 +1,7 @@
+{
+  "type": "commonjs",
+  "dependencies": {
+    "@types/react": "*",
+    "react": "*"
+  }
+}
diff --git a/tests/specs/run/package_json_type/commonjs/jsx/tsx.tsx b/tests/specs/run/package_json_type/commonjs/jsx/tsx.tsx
new file mode 100644
index 0000000000..ad8f0c0a9c
--- /dev/null
+++ b/tests/specs/run/package_json_type/commonjs/jsx/tsx.tsx
@@ -0,0 +1,5 @@
+import mod = require("./add.js");
+
+console.log(mod.add(2, 2));
+
+console.log(<div /> != null);
diff --git a/tests/specs/run/package_json_type/none/__test__.jsonc b/tests/specs/run/package_json_type/none/__test__.jsonc
new file mode 100644
index 0000000000..fa1d22ca18
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/__test__.jsonc
@@ -0,0 +1,18 @@
+{
+  "tests": {
+    "main_cjs": {
+      "args": "run --allow-read=. main_cjs.js",
+      "output": "main_cjs.out",
+      "exitCode": 1
+    },
+    "main_esm": {
+      "args": "run --allow-read=. main_esm.js",
+      "output": "main_esm.out",
+      "exitCode": 1
+    },
+    "sub_folder_cjs": {
+      "args": "run --allow-read=. sub_folder_cjs.js",
+      "output": "3\n"
+    }
+  }
+}
diff --git a/tests/specs/run/package_json_type/none/add.js b/tests/specs/run/package_json_type/none/add.js
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/package_json_type/none/commonjs/add.js b/tests/specs/run/package_json_type/none/commonjs/add.js
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/commonjs/add.js
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/specs/run/package_json_type/none/commonjs/package.json b/tests/specs/run/package_json_type/none/commonjs/package.json
new file mode 100644
index 0000000000..5bbefffbab
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/commonjs/package.json
@@ -0,0 +1,3 @@
+{
+  "type": "commonjs"
+}
diff --git a/tests/specs/run/package_json_type/none/deno.jsonc b/tests/specs/run/package_json_type/none/deno.jsonc
new file mode 100644
index 0000000000..35f64c86f4
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/deno.jsonc
@@ -0,0 +1,5 @@
+{
+  "unstable": [
+    "detect-cjs"
+  ]
+}
diff --git a/tests/specs/run/package_json_type/none/main_cjs.js b/tests/specs/run/package_json_type/none/main_cjs.js
new file mode 100644
index 0000000000..365e8e06f8
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/main_cjs.js
@@ -0,0 +1,2 @@
+const { add } = require("./add");
+console.log(add(1, 2));
diff --git a/tests/specs/run/package_json_type/none/main_cjs.out b/tests/specs/run/package_json_type/none/main_cjs.out
new file mode 100644
index 0000000000..8d34808fb1
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/main_cjs.out
@@ -0,0 +1,12 @@
+error: Uncaught (in promise) ReferenceError: require is not defined
+const { add } = require("./add");
+                ^
+    at file:///[WILDLINE]
+
+    info: Deno supports CommonJS modules in .cjs files, or when there's a package.json
+          with "type": "commonjs" option and --unstable-detect-cjs flag is used.
+    hint: Rewrite this module to ESM,
+          or change the file extension to .cjs,
+          or add package.json next to the file with "type": "commonjs" option
+          and pass --unstable-detect-cjs flag.
+    docs: https://docs.deno.com/go/commonjs
diff --git a/tests/specs/run/package_json_type/none/main_esm.js b/tests/specs/run/package_json_type/none/main_esm.js
new file mode 100644
index 0000000000..8c55f673b0
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/main_esm.js
@@ -0,0 +1,3 @@
+import { add } from "./add.js";
+
+console.log(add(1, 2));
diff --git a/tests/specs/run/package_json_type/none/main_esm.out b/tests/specs/run/package_json_type/none/main_esm.out
new file mode 100644
index 0000000000..5f16c5f350
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/main_esm.out
@@ -0,0 +1,4 @@
+error: Uncaught SyntaxError: The requested module './add.js' does not provide an export named 'add'
+import { add } from "./add.js";
+         ^
+    at <anonymous> (file:///[WILDLINE])
diff --git a/tests/specs/run/package_json_type/none/package.json b/tests/specs/run/package_json_type/none/package.json
new file mode 100644
index 0000000000..2c63c08510
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/package.json
@@ -0,0 +1,2 @@
+{
+}
diff --git a/tests/specs/run/package_json_type/none/sub_folder_cjs.js b/tests/specs/run/package_json_type/none/sub_folder_cjs.js
new file mode 100644
index 0000000000..ad04e67301
--- /dev/null
+++ b/tests/specs/run/package_json_type/none/sub_folder_cjs.js
@@ -0,0 +1,3 @@
+import { add } from "./commonjs/add.js";
+
+console.log(add(1, 2));
diff --git a/tests/specs/run/remote_cjs_main/__test__.jsonc b/tests/specs/run/remote_cjs_main/__test__.jsonc
new file mode 100644
index 0000000000..f45d09406e
--- /dev/null
+++ b/tests/specs/run/remote_cjs_main/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "run http://localhost:4545/run/add.cjs",
+  "output": "output.out",
+  "exitCode": 1
+}
diff --git a/tests/specs/run/remote_cjs_main/output.out b/tests/specs/run/remote_cjs_main/output.out
new file mode 100644
index 0000000000..360934acb7
--- /dev/null
+++ b/tests/specs/run/remote_cjs_main/output.out
@@ -0,0 +1,3 @@
+Download http://localhost:4545/run/add.cjs
+error: Remote CJS modules are not supported.
+  Specifier: http://localhost:4545/run/add.cjs
diff --git a/tests/specs/run/require_esm/main.out b/tests/specs/run/require_esm/main.out
index d17b1ead55..57b842b345 100644
--- a/tests/specs/run/require_esm/main.out
+++ b/tests/specs/run/require_esm/main.out
@@ -1,6 +1,6 @@
 [Module: null prototype] { sync_js: 1 }
 [Module: null prototype] { sync_mjs: 1 }
-error: Uncaught Error: Top-level await is not allowed in synchronous evaluation
+error: Uncaught (in promise) Error: Top-level await is not allowed in synchronous evaluation
     at loadESMFromCJS (node:module:[WILDCARD])
     at Module._compile (node:module:[WILDCARD])
     at Object.Module._extensions..js (node:module:[WILDCARD])
diff --git a/tests/specs/task/bin_package/task.out b/tests/specs/task/bin_package/task.out
index 69b4f75082..d2c130905a 100644
--- a/tests/specs/task/bin_package/task.out
+++ b/tests/specs/task/bin_package/task.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/bin@1.0.0
 Task sayhi cli-esm hi hello
diff --git a/tests/specs/task/bin_pkg_with_scope_auto/bin_auto.out b/tests/specs/task/bin_pkg_with_scope_auto/bin_auto.out
index 20865898e3..1eb196a7aa 100644
--- a/tests/specs/task/bin_pkg_with_scope_auto/bin_auto.out
+++ b/tests/specs/task/bin_pkg_with_scope_auto/bin_auto.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/bin/0.5.0.tgz
 Initialize @denotest/bin@0.5.0
diff --git a/tests/specs/task/bin_pkg_with_scope_auto/bin_none.out b/tests/specs/task/bin_pkg_with_scope_auto/bin_none.out
index 066c67bd8a..f44b234bf3 100644
--- a/tests/specs/task/bin_pkg_with_scope_auto/bin_none.out
+++ b/tests/specs/task/bin_pkg_with_scope_auto/bin_none.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/bin/0.5.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
diff --git a/tests/specs/task/bin_pkg_with_scope_none/bin_none.out b/tests/specs/task/bin_pkg_with_scope_none/bin_none.out
index 066c67bd8a..f44b234bf3 100644
--- a/tests/specs/task/bin_pkg_with_scope_none/bin_none.out
+++ b/tests/specs/task/bin_pkg_with_scope_none/bin_none.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/bin/0.5.0.tgz
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
diff --git a/tests/specs/task/both_package_json_selected/install.out b/tests/specs/task/both_package_json_selected/install.out
index 645501a3d9..08b70a0f21 100644
--- a/tests/specs/task/both_package_json_selected/install.out
+++ b/tests/specs/task/both_package_json_selected/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Initialize @denotest/bin@1.0.0
diff --git a/tests/specs/task/package_json_node_modules_dir_none/bin.out b/tests/specs/task/package_json_node_modules_dir_none/bin.out
index c86261d9e1..ff60cc3d0b 100644
--- a/tests/specs/task/package_json_node_modules_dir_none/bin.out
+++ b/tests/specs/task/package_json_node_modules_dir_none/bin.out
@@ -1,5 +1,5 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/1.0.0.tgz
 Download http://localhost:4260/@denotest/bin/0.5.0.tgz
 [UNORDERED_END]
diff --git a/tests/specs/test/document/__test__.jsonc b/tests/specs/test/document/__test__.jsonc
new file mode 100644
index 0000000000..cf73b4bab8
--- /dev/null
+++ b/tests/specs/test/document/__test__.jsonc
@@ -0,0 +1,9 @@
+{
+  "tests": {
+    "document": {
+      "args": "test document_test.js",
+      "exitCode": 1,
+      "output": "document_test.out"
+    }
+  }
+}
diff --git a/tests/specs/test/document/document_test.js b/tests/specs/test/document/document_test.js
new file mode 100644
index 0000000000..d60d6893cc
--- /dev/null
+++ b/tests/specs/test/document/document_test.js
@@ -0,0 +1,3 @@
+Deno.test("document query selector", () => {
+  document.querySelector("div");
+});
diff --git a/tests/specs/test/document/document_test.out b/tests/specs/test/document/document_test.out
new file mode 100644
index 0000000000..342cee0e47
--- /dev/null
+++ b/tests/specs/test/document/document_test.out
@@ -0,0 +1,22 @@
+running 1 test from ./document_test.js
+document query selector ... FAILED [WILDCARD]
+
+ ERRORS 
+
+document query selector => ./document_test.js:1:6
+error: ReferenceError: document is not defined
+  document.querySelector("div");
+  ^
+    at [WILDCARD]document_test.js:2:3
+
+    info: document global is not available in Deno.
+    hint: Use a library like happy-dom, deno_dom, linkedom or JSDom
+          and setup the document global according to the library documentation.
+
+ FAILURES 
+
+document query selector => ./document_test.js:1:6
+
+FAILED | 0 passed | 1 failed ([WILDCARD])
+
+error: Test failed
diff --git a/tests/specs/test/package_json_basic/install.out b/tests/specs/test/package_json_basic/install.out
index b8114c12a0..8f03ba6407 100644
--- a/tests/specs/test/package_json_basic/install.out
+++ b/tests/specs/test/package_json_basic/install.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
diff --git a/tests/specs/test/package_json_basic_auto_install/test.out b/tests/specs/test/package_json_basic_auto_install/test.out
index 2f109ef38e..749c395485 100644
--- a/tests/specs/test/package_json_basic_auto_install/test.out
+++ b/tests/specs/test/package_json_basic_auto_install/test.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file://[WILDCARD]/lib.test.ts
diff --git a/tests/testdata/compile/node_modules_symlink_outside/main_compile_folder.out b/tests/testdata/compile/node_modules_symlink_outside/main_compile_folder.out
index 2067bf1c60..1a7eb0a4f2 100644
--- a/tests/testdata/compile/node_modules_symlink_outside/main_compile_folder.out
+++ b/tests/testdata/compile/node_modules_symlink_outside/main_compile_folder.out
@@ -1,4 +1,4 @@
-Download http://localhost:4260/@denotest/esm-basic
+Download http://localhost:4260/@denotest%2fesm-basic
 Download http://localhost:4260/@denotest/esm-basic/1.0.0.tgz
 Initialize @denotest/esm-basic@1.0.0
 Check file:///[WILDCARD]/node_modules_symlink_outside/main.ts
diff --git a/tests/testdata/coverage/complex.ts b/tests/testdata/coverage/complex.ts
index d128b54373..316986cd22 100644
--- a/tests/testdata/coverage/complex.ts
+++ b/tests/testdata/coverage/complex.ts
@@ -1,3 +1,8 @@
+/**
+ * @module
+ * Complex module
+ */
+
 // This entire interface should be completely ignored by the coverage tool.
 export interface Complex {
   // These comments should be ignored.
@@ -19,6 +24,7 @@ function dependency(
   bar: string,
   baz: string,
 ): Complex {
+  // inline comment in tested function
   return {
     foo,
     bar,
@@ -34,6 +40,9 @@ export function complex(
   bar: string,
   baz: string,
 ): Complex {
+  /*
+   * block comment in tested function
+   */
   return dependency(
     foo,
     bar,
@@ -48,6 +57,7 @@ export function unused(
   bar: string,
   baz: string,
 ): Complex {
+  // inline comment in untested function
   return complex(
     foo,
     bar,
@@ -62,6 +72,9 @@ export const π = Math.PI;
 // And same applies for this one, this one is unused and will show up in
 // lacking coverage.
 export function ƒ(): number {
+  /*
+   * block comment in untested function
+   */
   return (
     0
   );
diff --git a/tests/testdata/coverage/complex_expected.lcov b/tests/testdata/coverage/complex_expected.lcov
index 94b86465ae..7e5c0f40f6 100644
--- a/tests/testdata/coverage/complex_expected.lcov
+++ b/tests/testdata/coverage/complex_expected.lcov
@@ -1,8 +1,8 @@
 SF:[WILDCARD]complex.ts
-FN:17,dependency
-FN:32,complex
-FN:46,unused
-FN:64,ƒ
+FN:22,dependency
+FN:38,complex
+FN:55,unused
+FN:74,ƒ
 FNDA:1,dependency
 FNDA:1,complex
 FNDA:0,unused
@@ -11,57 +11,41 @@ FNF:4
 FNH:2
 BRF:0
 BRH:0
-DA:1,1
-DA:13,1
-DA:14,1
-DA:15,1
-DA:16,1
-DA:17,2
-DA:18,2
-DA:19,2
-DA:20,2
 DA:22,2
 DA:23,2
 DA:24,2
 DA:25,2
-DA:26,2
-DA:27,2
-DA:29,1
-DA:30,1
-DA:31,1
-DA:32,1
-DA:33,1
-DA:34,1
-DA:35,1
-DA:37,2
-DA:38,2
-DA:39,2
-DA:40,2
-DA:42,2
-DA:44,1
-DA:45,1
-DA:46,0
-DA:47,0
-DA:48,0
-DA:49,0
-DA:51,0
-DA:52,0
-DA:53,0
-DA:54,0
+DA:28,2
+DA:29,2
+DA:30,2
+DA:31,2
+DA:32,2
+DA:33,2
+DA:38,1
+DA:39,1
+DA:40,1
+DA:41,1
+DA:46,2
+DA:47,2
+DA:48,2
+DA:49,2
+DA:51,2
+DA:55,0
 DA:56,0
-DA:58,1
-DA:59,1
-DA:60,1
-DA:62,1
-DA:63,1
+DA:57,0
+DA:58,0
+DA:61,0
+DA:62,0
+DA:63,0
 DA:64,0
-DA:65,0
 DA:66,0
-DA:68,0
 DA:70,1
-DA:71,0
-DA:73,1
-DA:74,1
-LH:37
-LF:51
+DA:74,0
+DA:78,0
+DA:79,0
+DA:81,0
+DA:84,0
+DA:87,1
+LH:21
+LF:35
 end_of_record
diff --git a/tests/testdata/coverage/complex_expected.out b/tests/testdata/coverage/complex_expected.out
index 3d5f6a0ab6..f626024b96 100644
--- a/tests/testdata/coverage/complex_expected.out
+++ b/tests/testdata/coverage/complex_expected.out
@@ -1,20 +1,21 @@
-cover [WILDCARD]/coverage/complex.ts ... 72.549% (37/51)
-  46 | export function unused(
-  47 |   foo: string,
-  48 |   bar: string,
-  49 |   baz: string,
+cover [WILDCARD]/coverage/complex.ts ... 60.000% (21/35)
+  55 | export function unused(
+  56 |   foo: string,
+  57 |   bar: string,
+  58 |   baz: string,
 -----|-----
-  51 |   return complex(
-  52 |     foo,
-  53 |     bar,
-  54 |     baz,
+  61 |   return complex(
+  62 |     foo,
+  63 |     bar,
+  64 |     baz,
 -----|-----
-  56 | }
+  66 | }
 -----|-----
-  64 | export function ƒ(): number {
-  65 |   return (
-  66 |     0
+  74 | export function ƒ(): number {
 -----|-----
-  68 | }
+  78 |   return (
+  79 |     0
 -----|-----
-  71 | console.log("%s", () => 1);
+  81 | }
+-----|-----
+  84 | console.log("%s", () => 1);
diff --git a/tests/testdata/npm/deno_run_cowsay_no_permissions.out b/tests/testdata/npm/deno_run_cowsay_no_permissions.out
index 6434620e2e..25b79d9a7d 100644
--- a/tests/testdata/npm/deno_run_cowsay_no_permissions.out
+++ b/tests/testdata/npm/deno_run_cowsay_no_permissions.out
@@ -1,2 +1,2 @@
-error: Uncaught NotCapable: Requires read access to <CWD>, specify the required permissions during compilation using `deno compile --allow-read`
+error: Uncaught (in promise) NotCapable: Requires read access to <CWD>, specify the required permissions during compilation using `deno compile --allow-read`
 [WILDCARD]
diff --git a/tests/testdata/npm/peer_deps_with_copied_folders/main.out b/tests/testdata/npm/peer_deps_with_copied_folders/main.out
index 3c133bcde4..b7a5835577 100644
--- a/tests/testdata/npm/peer_deps_with_copied_folders/main.out
+++ b/tests/testdata/npm/peer_deps_with_copied_folders/main.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/testdata/npm/peer_deps_with_copied_folders/main_node_modules_reload.out b/tests/testdata/npm/peer_deps_with_copied_folders/main_node_modules_reload.out
index 9c81452118..18d7f7865b 100644
--- a/tests/testdata/npm/peer_deps_with_copied_folders/main_node_modules_reload.out
+++ b/tests/testdata/npm/peer_deps_with_copied_folders/main_node_modules_reload.out
@@ -1,7 +1,7 @@
 [UNORDERED_START]
-Download http://localhost:4260/@denotest/peer-dep-test-child
-Download http://localhost:4260/@denotest/peer-dep-test-grandchild
-Download http://localhost:4260/@denotest/peer-dep-test-peer
+Download http://localhost:4260/@denotest%2fpeer-dep-test-child
+Download http://localhost:4260/@denotest%2fpeer-dep-test-grandchild
+Download http://localhost:4260/@denotest%2fpeer-dep-test-peer
 [UNORDERED_END]
 [UNORDERED_START]
 Download http://localhost:4260/@denotest/peer-dep-test-child/1.0.0.tgz
diff --git a/tests/testdata/npm/run_existing_npm_package/main.out b/tests/testdata/npm/run_existing_npm_package/main.out
index 147ed6a995..373059db53 100644
--- a/tests/testdata/npm/run_existing_npm_package/main.out
+++ b/tests/testdata/npm/run_existing_npm_package/main.out
@@ -1,3 +1,3 @@
-Download http://localhost:4260/@denotest/bin
+Download http://localhost:4260/@denotest%2fbin
 Download http://localhost:4260/@denotest/bin/0.5.0.tgz
 Initialize @denotest/bin@0.5.0
diff --git a/tests/testdata/run/add.cjs b/tests/testdata/run/add.cjs
new file mode 100644
index 0000000000..2a886fbc18
--- /dev/null
+++ b/tests/testdata/run/add.cjs
@@ -0,0 +1,3 @@
+module.exports.add = function (a, b) {
+  return a + b;
+};
diff --git a/tests/unit/console_test.ts b/tests/unit/console_test.ts
index 878d17ae33..06f5dd7e61 100644
--- a/tests/unit/console_test.ts
+++ b/tests/unit/console_test.ts
@@ -1162,7 +1162,7 @@ Deno.test(function consoleTestWithIntegerFormatSpecifier() {
   assertEquals(stringify("%i"), "%i");
   assertEquals(stringify("%i", 42.0), "42");
   assertEquals(stringify("%i", 42), "42");
-  assertEquals(stringify("%i", "42"), "NaN");
+  assertEquals(stringify("%i", "42"), "42");
   assertEquals(stringify("%i", 1.5), "1");
   assertEquals(stringify("%i", -0.5), "0");
   assertEquals(stringify("%i", ""), "NaN");
@@ -1172,7 +1172,7 @@ Deno.test(function consoleTestWithIntegerFormatSpecifier() {
   assertEquals(stringify("%d", 12345678901234567890123), "1");
   assertEquals(
     stringify("%i", 12345678901234567890123n),
-    "12345678901234567890123n",
+    "1.2345678901234568e+22",
   );
 });
 
@@ -1180,13 +1180,13 @@ Deno.test(function consoleTestWithFloatFormatSpecifier() {
   assertEquals(stringify("%f"), "%f");
   assertEquals(stringify("%f", 42.0), "42");
   assertEquals(stringify("%f", 42), "42");
-  assertEquals(stringify("%f", "42"), "NaN");
+  assertEquals(stringify("%f", "42"), "42");
   assertEquals(stringify("%f", 1.5), "1.5");
   assertEquals(stringify("%f", -0.5), "-0.5");
   assertEquals(stringify("%f", Math.PI), "3.141592653589793");
   assertEquals(stringify("%f", ""), "NaN");
   assertEquals(stringify("%f", Symbol("foo")), "NaN");
-  assertEquals(stringify("%f", 5n), "NaN");
+  assertEquals(stringify("%f", 5n), "5");
   assertEquals(stringify("%f %f", 42, 43), "42 43");
   assertEquals(stringify("%f %f", 42), "42 %f");
 });
@@ -1227,6 +1227,7 @@ Deno.test(function consoleParseCssColor() {
   assertEquals(parseCssColor("inherit"), null);
   assertEquals(parseCssColor("black"), [0, 0, 0]);
   assertEquals(parseCssColor("darkmagenta"), [139, 0, 139]);
+  assertEquals(parseCssColor("darkMaGenta"), [139, 0, 139]);
   assertEquals(parseCssColor("slateblue"), [106, 90, 205]);
   assertEquals(parseCssColor("#ffaa00"), [255, 170, 0]);
   assertEquals(parseCssColor("#ffAA00"), [255, 170, 0]);
diff --git a/tests/unit/signal_test.ts b/tests/unit/signal_test.ts
index 65b5ba78e1..8923aa75bf 100644
--- a/tests/unit/signal_test.ts
+++ b/tests/unit/signal_test.ts
@@ -5,101 +5,101 @@ Deno.test(
   { ignore: Deno.build.os !== "windows" },
   function signalsNotImplemented() {
     const msg =
-      "Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK).";
+      "Windows only supports ctrl-c (SIGINT) and ctrl-break (SIGBREAK), but got ";
     assertThrows(
       () => {
         Deno.addSignalListener("SIGALRM", () => {});
       },
       Error,
-      msg,
+      msg + "SIGALRM",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGCHLD", () => {});
       },
       Error,
-      msg,
+      msg + "SIGCHLD",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGHUP", () => {});
       },
       Error,
-      msg,
+      msg + "SIGHUP",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGIO", () => {});
       },
       Error,
-      msg,
+      msg + "SIGIO",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGPIPE", () => {});
       },
       Error,
-      msg,
+      msg + "SIGPIPE",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGQUIT", () => {});
       },
       Error,
-      msg,
+      msg + "SIGQUIT",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGTERM", () => {});
       },
       Error,
-      msg,
+      msg + "SIGTERM",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGUSR1", () => {});
       },
       Error,
-      msg,
+      msg + "SIGUSR1",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGUSR2", () => {});
       },
       Error,
-      msg,
+      msg + "SIGUSR2",
     );
     assertThrows(
       () => {
         Deno.addSignalListener("SIGWINCH", () => {});
       },
       Error,
-      msg,
+      msg + "SIGWINCH",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGKILL", () => {}),
       Error,
-      msg,
+      msg + "SIGKILL",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGSTOP", () => {}),
       Error,
-      msg,
+      msg + "SIGSTOP",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGILL", () => {}),
       Error,
-      msg,
+      msg + "SIGILL",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGFPE", () => {}),
       Error,
-      msg,
+      msg + "SIGFPE",
     );
     assertThrows(
       () => Deno.addSignalListener("SIGSEGV", () => {}),
       Error,
-      msg,
+      msg + "SIGSEGV",
     );
   },
 );
diff --git a/tests/unit_node/child_process_test.ts b/tests/unit_node/child_process_test.ts
index f776fa4acd..0ea3c46cf0 100644
--- a/tests/unit_node/child_process_test.ts
+++ b/tests/unit_node/child_process_test.ts
@@ -1045,3 +1045,19 @@ Deno.test(async function sendAfterClosedThrows() {
 
   await timeout.promise;
 });
+
+Deno.test(async function noWarningsFlag() {
+  const code = ``;
+  const file = await Deno.makeTempFile();
+  await Deno.writeTextFile(file, code);
+  const timeout = withTimeout<void>();
+  const child = CP.fork(file, [], {
+    execArgv: ["--no-warnings"],
+    stdio: ["inherit", "inherit", "inherit", "ipc"],
+  });
+  child.on("close", () => {
+    timeout.resolve();
+  });
+
+  await timeout.promise;
+});
diff --git a/tests/unit_node/crypto/crypto_key_test.ts b/tests/unit_node/crypto/crypto_key_test.ts
index 7995ce5d3f..3c7ad44232 100644
--- a/tests/unit_node/crypto/crypto_key_test.ts
+++ b/tests/unit_node/crypto/crypto_key_test.ts
@@ -656,3 +656,24 @@ z6TExWlQMjt66nV7R8cRAkzmABrG+NW3e8Zpac7Lkuv+zu0S+K7c
   assertEquals(publicKey.type, "public");
   assertEquals(publicKey.asymmetricKeyType, "rsa");
 });
+
+// https://github.com/denoland/deno/issues/26188
+Deno.test("generateKeyPair large pem", function () {
+  const passphrase = "mypassphrase";
+  const cipher = "aes-256-cbc";
+  const modulusLength = 4096;
+
+  generateKeyPairSync("rsa", {
+    modulusLength,
+    publicKeyEncoding: {
+      type: "spki",
+      format: "pem",
+    },
+    privateKeyEncoding: {
+      type: "pkcs8",
+      format: "pem",
+      cipher,
+      passphrase,
+    },
+  });
+});
diff --git a/tests/unit_node/crypto/crypto_misc_test.ts b/tests/unit_node/crypto/crypto_misc_test.ts
index 47a48b1bf8..007009339d 100644
--- a/tests/unit_node/crypto/crypto_misc_test.ts
+++ b/tests/unit_node/crypto/crypto_misc_test.ts
@@ -1,5 +1,6 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
-import { randomFillSync, randomUUID } from "node:crypto";
+import { randomFillSync, randomUUID, timingSafeEqual } from "node:crypto";
+import { Buffer } from "node:buffer";
 import { assert, assertEquals } from "../../unit/test_util.ts";
 import { assertNotEquals } from "@std/assert";
 
@@ -28,3 +29,10 @@ Deno.test("[node/crypto.randomFillSync] array buffer view", () => {
   assertEquals(buf.subarray(0, 8), new Uint8Array(8));
   assertEquals(buf.subarray(24, 32), new Uint8Array(8));
 });
+
+Deno.test("[node/crypto.timingSafeEqual] compares equal Buffer with different byteOffset", () => {
+  const a = Buffer.from([212, 213]);
+  const b = Buffer.from([0, 0, 0, 0, 0, 0, 0, 0, 212, 213]).subarray(8);
+
+  assert(timingSafeEqual(a, b));
+});
diff --git a/tests/unit_node/fs_test.ts b/tests/unit_node/fs_test.ts
index 2d1465aec6..631608d7cc 100644
--- a/tests/unit_node/fs_test.ts
+++ b/tests/unit_node/fs_test.ts
@@ -1,11 +1,13 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-import { assert, assertEquals, assertThrows } from "@std/assert";
+/// <reference lib="deno.ns" />
+import { assert, assertEquals, assertRejects, assertThrows } from "@std/assert";
 import { join } from "node:path";
 import { tmpdir } from "node:os";
 import {
   closeSync,
   constants,
+  copyFileSync,
   createWriteStream,
   existsSync,
   lstatSync,
@@ -20,9 +22,11 @@ import {
 } from "node:fs";
 import {
   constants as fsPromiseConstants,
+  copyFile,
   cp,
   FileHandle,
   open,
+  stat,
   writeFile,
 } from "node:fs/promises";
 import process from "node:process";
@@ -120,6 +124,48 @@ Deno.test(
   },
 );
 
+Deno.test(
+  "[node/fs statSync] throw error with path information",
+  () => {
+    const file = "non-exist-file";
+    const fileUrl = new URL(file, import.meta.url);
+
+    assertThrows(() => {
+      statSync(file);
+    }, "Error: ENOENT: no such file or directory, stat 'non-exist-file'");
+
+    assertThrows(() => {
+      statSync(fileUrl);
+    }, `Error: ENOENT: no such file or directory, stat '${fileUrl.pathname}'`);
+  },
+);
+
+Deno.test(
+  "[node/fs/promises stat] throw error with path information",
+  async () => {
+    const file = "non-exist-file";
+    const fileUrl = new URL(file, import.meta.url);
+
+    try {
+      await stat(file);
+    } catch (error: unknown) {
+      assertEquals(
+        `${error}`,
+        "Error: ENOENT: no such file or directory, stat 'non-exist-file'",
+      );
+    }
+
+    try {
+      await stat(fileUrl);
+    } catch (error: unknown) {
+      assertEquals(
+        `${error}`,
+        `Error: ENOENT: no such file or directory, stat '${fileUrl.pathname}'`,
+      );
+    }
+  },
+);
+
 Deno.test(
   "[node/fs/promises cp] copy file",
   async () => {
@@ -212,3 +258,32 @@ Deno.test("[node/fs] readSync works", () => {
   assertEquals(bytesRead, 12);
   closeSync(fd!);
 });
+
+Deno.test("[node/fs] copyFile COPYFILE_EXCL works", async () => {
+  const dir = mkdtempSync(join(tmpdir(), "foo-"));
+  const src = join(dir, "src.txt");
+  const dest = join(dir, "dest.txt");
+  await writeFile(src, "");
+  await copyFile(src, dest, fsPromiseConstants.COPYFILE_EXCL);
+  assert(existsSync(dest));
+  await assertRejects(() =>
+    copyFile(src, dest, fsPromiseConstants.COPYFILE_EXCL)
+  );
+  const dest2 = join(dir, "dest2.txt");
+  copyFileSync(src, dest2, fsPromiseConstants.COPYFILE_EXCL);
+  assert(existsSync(dest2));
+  assertThrows(() =>
+    copyFileSync(src, dest2, fsPromiseConstants.COPYFILE_EXCL)
+  );
+});
+
+Deno.test("[node/fs] statSync throws ENOENT for invalid path containing colon in it", () => {
+  // deno-lint-ignore no-explicit-any
+  const err: any = assertThrows(() => {
+    // Note: Deno.stat throws ERROR_INVALID_NAME (os error 123) instead of
+    // ERROR_FILE_NOT_FOUND (os error 2) on windows. This case checks that
+    // ERROR_INVALID_NAME is mapped to ENOENT correctly on node compat layer.
+    statSync("jsr:@std/assert");
+  });
+  assertEquals(err.code, "ENOENT");
+});
diff --git a/tests/unit_node/http_test.ts b/tests/unit_node/http_test.ts
index f85b1466b5..2b3b8f509f 100644
--- a/tests/unit_node/http_test.ts
+++ b/tests/unit_node/http_test.ts
@@ -3,10 +3,14 @@
 // deno-lint-ignore-file no-console
 
 import EventEmitter from "node:events";
-import http, { type RequestOptions, type ServerResponse } from "node:http";
+import http, {
+  IncomingMessage,
+  type RequestOptions,
+  ServerResponse,
+} from "node:http";
 import url from "node:url";
 import https from "node:https";
-import net from "node:net";
+import net, { Socket } from "node:net";
 import fs from "node:fs";
 import { text } from "node:stream/consumers";
 
@@ -1143,6 +1147,34 @@ Deno.test("[node/http] ServerResponse appendHeader set-cookie", async () => {
   await promise;
 });
 
+Deno.test("[node/http] ServerResponse header names case insensitive", async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+  const server = http.createServer((_req, res) => {
+    res.setHeader("Content-Length", "12345");
+    res.removeHeader("content-length");
+    assertEquals(res.getHeader("Content-Length"), undefined);
+    assert(!res.hasHeader("Content-Length"));
+    res.appendHeader("content-length", "12345");
+    res.removeHeader("Content-Length");
+    assertEquals(res.getHeader("content-length"), undefined);
+    assert(!res.hasHeader("content-length"));
+    res.end("Hello World");
+  });
+
+  server.listen(async () => {
+    const { port } = server.address() as { port: number };
+    const res = await fetch(`http://localhost:${port}`);
+    assertEquals(res.headers.get("Content-Length"), null);
+    assertEquals(res.headers.get("content-length"), null);
+    assertEquals(await res.text(), "Hello World");
+    server.close(() => {
+      resolve();
+    });
+  });
+
+  await promise;
+});
+
 Deno.test("[node/http] IncomingMessage override", () => {
   const req = new http.IncomingMessage(new net.Socket());
   // https://github.com/dougmoscrop/serverless-http/blob/3aaa6d0fe241109a8752efb011c242d249f32368/lib/request.js#L20-L30
@@ -1672,3 +1704,75 @@ Deno.test("[node/http] upgraded socket closes when the server closed without clo
   await clientSocketClosed.promise;
   await serverProcessClosed.promise;
 });
+
+// deno-lint-ignore require-await
+Deno.test("[node/http] ServerResponse.call()", async () => {
+  function Wrapper(this: unknown, req: IncomingMessage) {
+    ServerResponse.call(this, req);
+  }
+  Object.setPrototypeOf(Wrapper.prototype, ServerResponse.prototype);
+
+  // deno-lint-ignore no-explicit-any
+  const wrapper = new (Wrapper as any)(new IncomingMessage(new Socket()));
+
+  assert(wrapper instanceof ServerResponse);
+});
+
+Deno.test("[node/http] ServerResponse _header", async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+  const server = http.createServer((_req, res) => {
+    assert(Object.hasOwn(res, "_header"));
+    res.end();
+  });
+
+  server.listen(async () => {
+    const { port } = server.address() as { port: number };
+    const res = await fetch(`http://localhost:${port}`);
+    await res.body?.cancel();
+    server.close(() => {
+      resolve();
+    });
+  });
+
+  await promise;
+});
+
+Deno.test("[node/http] ServerResponse connection", async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+  const server = http.createServer((_req, res) => {
+    assert(Object.hasOwn(res, "connection"));
+    assert(res.connection instanceof Socket);
+    res.end();
+  });
+
+  server.listen(async () => {
+    const { port } = server.address() as { port: number };
+    const res = await fetch(`http://localhost:${port}`);
+    await res.body?.cancel();
+    server.close(() => {
+      resolve();
+    });
+  });
+
+  await promise;
+});
+
+Deno.test("[node/http] ServerResponse socket", async () => {
+  const { promise, resolve } = Promise.withResolvers<void>();
+  const server = http.createServer((_req, res) => {
+    assert(Object.hasOwn(res, "socket"));
+    assert(res.socket instanceof Socket);
+    res.end();
+  });
+
+  server.listen(async () => {
+    const { port } = server.address() as { port: number };
+    const res = await fetch(`http://localhost:${port}`);
+    await res.body?.cancel();
+    server.close(() => {
+      resolve();
+    });
+  });
+
+  await promise;
+});
diff --git a/tests/unit_node/process_test.ts b/tests/unit_node/process_test.ts
index add9e1280a..f9138c8f08 100644
--- a/tests/unit_node/process_test.ts
+++ b/tests/unit_node/process_test.ts
@@ -25,7 +25,6 @@ import {
   assertThrows,
   fail,
 } from "@std/assert";
-import { assertSpyCall, assertSpyCalls, spy } from "@std/testing/mock";
 import { stripAnsiCode } from "@std/fmt/colors";
 import * as path from "@std/path";
 import { delay } from "@std/async/delay";
@@ -239,33 +238,6 @@ Deno.test({
   },
 });
 
-Deno.test({
-  name: "process.on - ignored signals on windows",
-  ignore: Deno.build.os !== "windows",
-  fn() {
-    const ignoredSignals = ["SIGHUP", "SIGUSR1", "SIGUSR2"];
-
-    for (const signal of ignoredSignals) {
-      using consoleSpy = spy(console, "warn");
-      const handler = () => {};
-      process.on(signal, handler);
-      process.off(signal, handler);
-      assertSpyCall(consoleSpy, 0, {
-        args: [`Ignoring signal "${signal}" on Windows`],
-      });
-    }
-
-    {
-      using consoleSpy = spy(console, "warn");
-      const handler = () => {};
-      process.on("SIGTERM", handler);
-      process.off("SIGTERM", handler);
-      // No warning is made for SIGTERM
-      assertSpyCalls(consoleSpy, 0);
-    }
-  },
-});
-
 Deno.test(
   { permissions: { run: true, read: true } },
   async function processKill() {
@@ -691,6 +663,16 @@ Deno.test({
       assertStrictEquals(process.stdout.clearLine, undefined);
       assertStrictEquals(process.stdout.clearScreenDown, undefined);
     }
+
+    // Allows overwriting `process.stdout.isTTY`
+    // https://github.com/denoland/deno/issues/26123
+    const original = process.stdout.isTTY;
+    try {
+      process.stdout.isTTY = !isTTY;
+      assertEquals(process.stdout.isTTY, !isTTY);
+    } finally {
+      process.stdout.isTTY = original;
+    }
   },
 });
 
@@ -1165,3 +1147,8 @@ Deno.test("process.cpuUsage()", () => {
   assert(typeof cpuUsage.user === "number");
   assert(typeof cpuUsage.system === "number");
 });
+
+Deno.test("process.stdout.columns writable", () => {
+  process.stdout.columns = 80;
+  assertEquals(process.stdout.columns, 80);
+});
diff --git a/tests/unit_node/tls_test.ts b/tests/unit_node/tls_test.ts
index 93eacd5ec2..43d6205b0b 100644
--- a/tests/unit_node/tls_test.ts
+++ b/tests/unit_node/tls_test.ts
@@ -229,3 +229,31 @@ Deno.test("tls.rootCertificates is not empty", () => {
     (tls.rootCertificates as string[]).push("new cert");
   }, TypeError);
 });
+
+Deno.test("TLSSocket.alpnProtocol is set for client", async () => {
+  const listener = Deno.listenTls({
+    hostname: "localhost",
+    port: 0,
+    key,
+    cert,
+    alpnProtocols: ["a"],
+  });
+  const outgoing = tls.connect({
+    host: "::1",
+    servername: "localhost",
+    port: listener.addr.port,
+    ALPNProtocols: ["a"],
+    secureContext: {
+      ca: rootCaCert,
+      // deno-lint-ignore no-explicit-any
+    } as any,
+  });
+
+  const conn = await listener.accept();
+  const handshake = await conn.handshake();
+  assertEquals(handshake.alpnProtocol, "a");
+  conn.close();
+  outgoing.destroy();
+  listener.close();
+  await new Promise((resolve) => outgoing.on("close", resolve));
+});
diff --git a/tests/unit_node/util_test.ts b/tests/unit_node/util_test.ts
index edd5002623..6267018b12 100644
--- a/tests/unit_node/util_test.ts
+++ b/tests/unit_node/util_test.ts
@@ -348,3 +348,13 @@ Deno.test("[util] aborted()", async () => {
   await promise;
   assertEquals(done, true);
 });
+
+Deno.test("[util] styleText()", () => {
+  const redText = util.styleText("red", "error");
+  assertEquals(redText, "\x1B[31merror\x1B[39m");
+});
+
+Deno.test("[util] styleText() with array of formats", () => {
+  const colored = util.styleText(["red", "green"], "error");
+  assertEquals(colored, "\x1b[32m\x1b[31merror\x1b[39m\x1b[39m");
+});
diff --git a/tests/util/server/Cargo.toml b/tests/util/server/Cargo.toml
index a321501b85..aee7ef0be6 100644
--- a/tests/util/server/Cargo.toml
+++ b/tests/util/server/Cargo.toml
@@ -35,7 +35,7 @@ lazy-regex.workspace = true
 libc.workspace = true
 lsp-types.workspace = true
 monch.workspace = true
-nix.workspace = true
+nix = { workspace = true, features = ["fs", "term", "signal"] }
 once_cell.workspace = true
 os_pipe.workspace = true
 parking_lot.workspace = true
diff --git a/tests/util/server/src/builders.rs b/tests/util/server/src/builders.rs
index 4a4b6a7613..3bf5c704a1 100644
--- a/tests/util/server/src/builders.rs
+++ b/tests/util/server/src/builders.rs
@@ -78,6 +78,7 @@ impl DiagnosticLogger {
         logger.write_all(text.as_ref().as_bytes()).unwrap();
         logger.write_all(b"\n").unwrap();
       }
+      #[allow(clippy::print_stderr)]
       None => eprintln!("{}", text.as_ref()),
     }
   }
diff --git a/tests/util/server/src/fs.rs b/tests/util/server/src/fs.rs
index 47d0d61fa1..7feb0799ae 100644
--- a/tests/util/server/src/fs.rs
+++ b/tests/util/server/src/fs.rs
@@ -285,7 +285,10 @@ impl PathRef {
   #[track_caller]
   pub fn assert_matches_file(&self, wildcard_file: impl AsRef<Path>) -> &Self {
     let wildcard_file = testdata_path().join(wildcard_file);
-    println!("output path {}", wildcard_file);
+    #[allow(clippy::print_stdout)]
+    {
+      println!("output path {}", wildcard_file);
+    }
     let expected_text = wildcard_file.read_to_string();
     self.assert_matches_text(&expected_text)
   }
diff --git a/tests/util/server/src/lib.rs b/tests/util/server/src/lib.rs
index 88e8287e08..67dbcd820c 100644
--- a/tests/util/server/src/lib.rs
+++ b/tests/util/server/src/lib.rs
@@ -1,8 +1,5 @@
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-#![allow(clippy::print_stdout)]
-#![allow(clippy::print_stderr)]
-
 use std::collections::HashMap;
 use std::env;
 use std::io::Write;
@@ -302,12 +299,15 @@ async fn get_tcp_listener_stream(
     .collect::<Vec<_>>();
 
   // Eye catcher for HttpServerCount
-  println!("ready: {name} on {:?}", addresses);
+  #[allow(clippy::print_stdout)]
+  {
+    println!("ready: {name} on {:?}", addresses);
+  }
 
   futures::stream::select_all(listeners)
 }
 
-pub const TEST_SERVERS_COUNT: usize = 30;
+pub const TEST_SERVERS_COUNT: usize = 32;
 
 #[derive(Default)]
 struct HttpServerCount {
@@ -345,7 +345,10 @@ struct HttpServerStarter {
 
 impl Default for HttpServerStarter {
   fn default() -> Self {
-    println!("test_server starting...");
+    #[allow(clippy::print_stdout)]
+    {
+      println!("test_server starting...");
+    }
     let mut test_server = Command::new(test_server_path())
       .current_dir(testdata_path())
       .stdout(Stdio::piped())
@@ -479,6 +482,7 @@ pub fn run_collect(
   } = prog.wait_with_output().expect("failed to wait on child");
   let stdout = String::from_utf8(stdout).unwrap();
   let stderr = String::from_utf8(stderr).unwrap();
+  #[allow(clippy::print_stderr)]
   if expect_success != status.success() {
     eprintln!("stdout: <<<{stdout}>>>");
     eprintln!("stderr: <<<{stderr}>>>");
@@ -539,6 +543,7 @@ pub fn run_and_collect_output_with_args(
   } = deno.wait_with_output().expect("failed to wait on child");
   let stdout = String::from_utf8(stdout).unwrap();
   let stderr = String::from_utf8(stderr).unwrap();
+  #[allow(clippy::print_stderr)]
   if expect_success != status.success() {
     eprintln!("stdout: <<<{stdout}>>>");
     eprintln!("stderr: <<<{stderr}>>>");
@@ -563,6 +568,7 @@ pub fn deno_cmd_with_deno_dir(deno_dir: &TempDir) -> TestCommandBuilder {
     .env("JSR_URL", jsr_registry_unset_url())
 }
 
+#[allow(clippy::print_stdout)]
 pub fn run_powershell_script_file(
   script_file_path: &str,
   args: Vec<&str>,
@@ -654,6 +660,7 @@ impl<'a> CheckOutputIntegrationTest<'a> {
 }
 
 pub fn wildcard_match(pattern: &str, text: &str) -> bool {
+  #[allow(clippy::print_stderr)]
   match wildcard_match_detailed(pattern, text) {
     WildcardMatchResult::Success => true,
     WildcardMatchResult::Fail(debug_output) => {
diff --git a/tests/util/server/src/lsp.rs b/tests/util/server/src/lsp.rs
index ffe72b88af..d34deb2161 100644
--- a/tests/util/server/src/lsp.rs
+++ b/tests/util/server/src/lsp.rs
@@ -157,6 +157,7 @@ impl LspStdoutReader {
     self.pending_messages.0.lock().len()
   }
 
+  #[allow(clippy::print_stderr)]
   pub fn output_pending_messages(&self) {
     let messages = self.pending_messages.0.lock();
     eprintln!("{:?}", messages);
@@ -308,34 +309,6 @@ impl InitializeParamsBuilder {
     self
   }
 
-  pub fn enable_inlay_hints(&mut self) -> &mut Self {
-    let options = self.initialization_options_mut();
-    options.insert(
-      "inlayHints".to_string(),
-      json!({
-        "parameterNames": {
-          "enabled": "all"
-        },
-        "parameterTypes": {
-          "enabled": true
-        },
-        "variableTypes": {
-          "enabled": true
-        },
-        "propertyDeclarationTypes": {
-          "enabled": true
-        },
-        "functionLikeReturnTypes": {
-          "enabled": true
-        },
-        "enumMemberValues": {
-          "enabled": true
-        }
-      }),
-    );
-    self
-  }
-
   pub fn disable_testing_api(&mut self) -> &mut Self {
     let obj = self
       .params
@@ -601,6 +574,7 @@ impl LspClientBuilder {
         for line in stderr.lines() {
           match line {
             Ok(line) => {
+              #[allow(clippy::print_stderr)]
               if print_stderr {
                 eprintln!("{}", line);
               }
@@ -615,7 +589,10 @@ impl LspClientBuilder {
                       continue;
                     }
                     Err(err) => {
-                      eprintln!("failed to parse perf record: {:#}", err);
+                      #[allow(clippy::print_stderr)]
+                      {
+                        eprintln!("failed to parse perf record: {:#}", err);
+                      }
                     }
                   }
                 }
@@ -810,11 +787,14 @@ impl LspClient {
       std::thread::sleep(Duration::from_millis(20));
     }
 
-    eprintln!("==== STDERR OUTPUT ====");
-    for line in found_lines {
-      eprintln!("{}", line)
+    #[allow(clippy::print_stderr)]
+    {
+      eprintln!("==== STDERR OUTPUT ====");
+      for line in found_lines {
+        eprintln!("{}", line)
+      }
+      eprintln!("== END STDERR OUTPUT ==");
     }
-    eprintln!("== END STDERR OUTPUT ==");
 
     panic!("Timed out waiting on condition.")
   }
diff --git a/tests/util/server/src/npm.rs b/tests/util/server/src/npm.rs
index f1c341738a..31686fa854 100644
--- a/tests/util/server/src/npm.rs
+++ b/tests/util/server/src/npm.rs
@@ -18,6 +18,7 @@ use crate::PathRef;
 
 pub const DENOTEST_SCOPE_NAME: &str = "@denotest";
 pub const DENOTEST2_SCOPE_NAME: &str = "@denotest2";
+pub const DENOTEST3_SCOPE_NAME: &str = "@denotest3";
 
 pub static PUBLIC_TEST_NPM_REGISTRY: Lazy<TestNpmRegistry> = Lazy::new(|| {
   TestNpmRegistry::new(
@@ -54,6 +55,18 @@ pub static PRIVATE_TEST_NPM_REGISTRY_2: Lazy<TestNpmRegistry> =
     )
   });
 
+pub static PRIVATE_TEST_NPM_REGISTRY_3: Lazy<TestNpmRegistry> =
+  Lazy::new(|| {
+    TestNpmRegistry::new(
+      NpmRegistryKind::Private,
+      &format!(
+        "http://localhost:{}",
+        crate::servers::PRIVATE_NPM_REGISTRY_3_PORT
+      ),
+      "npm-private3",
+    )
+  });
+
 pub enum NpmRegistryKind {
   Public,
   Private,
@@ -161,6 +174,17 @@ impl TestNpmRegistry {
       return Some((DENOTEST2_SCOPE_NAME, package_name_with_path));
     }
 
+    let prefix1 = format!("/{}/", DENOTEST3_SCOPE_NAME);
+    let prefix2 = format!("/{}%2f", DENOTEST3_SCOPE_NAME);
+
+    let maybe_package_name_with_path = uri_path
+      .strip_prefix(&prefix1)
+      .or_else(|| uri_path.strip_prefix(&prefix2));
+
+    if let Some(package_name_with_path) = maybe_package_name_with_path {
+      return Some((DENOTEST3_SCOPE_NAME, package_name_with_path));
+    }
+
     None
   }
 }
diff --git a/tests/util/server/src/pty.rs b/tests/util/server/src/pty.rs
index 5d8049fee9..07659262cf 100644
--- a/tests/util/server/src/pty.rs
+++ b/tests/util/server/src/pty.rs
@@ -61,7 +61,10 @@ impl Pty {
     if is_windows && *IS_CI {
       // the pty tests don't really start up on the windows CI for some reason
       // so ignore them for now
-      eprintln!("Ignoring windows CI.");
+      #[allow(clippy::print_stderr)]
+      {
+        eprintln!("Ignoring windows CI.");
+      }
       false
     } else {
       true
@@ -250,11 +253,14 @@ impl Pty {
     }
 
     let text = self.next_text();
-    eprintln!(
-      "------ Start Full Text ------\n{:?}\n------- End Full Text -------",
-      String::from_utf8_lossy(&self.read_bytes)
-    );
-    eprintln!("Next text: {:?}", text);
+    #[allow(clippy::print_stderr)]
+    {
+      eprintln!(
+        "------ Start Full Text ------\n{:?}\n------- End Full Text -------",
+        String::from_utf8_lossy(&self.read_bytes)
+      );
+      eprintln!("Next text: {:?}", text);
+    }
 
     false
   }
@@ -297,10 +303,12 @@ fn setup_pty(fd: i32) {
   use nix::sys::termios::tcsetattr;
   use nix::sys::termios::SetArg;
 
-  let mut term = tcgetattr(fd).unwrap();
+  // SAFETY: Nix crate requires value to implement the AsFd trait
+  let as_fd = unsafe { std::os::fd::BorrowedFd::borrow_raw(fd) };
+  let mut term = tcgetattr(as_fd).unwrap();
   // disable cooked mode
   term.local_flags.remove(termios::LocalFlags::ICANON);
-  tcsetattr(fd, SetArg::TCSANOW, &term).unwrap();
+  tcsetattr(as_fd, SetArg::TCSANOW, &term).unwrap();
 
   // turn on non-blocking mode so we get timeouts
   let flags = fcntl(fd, FcntlArg::F_GETFL).unwrap();
diff --git a/tests/util/server/src/servers/hyper_utils.rs b/tests/util/server/src/servers/hyper_utils.rs
index c2db7ea668..8e01151ed4 100644
--- a/tests/util/server/src/servers/hyper_utils.rs
+++ b/tests/util/server/src/servers/hyper_utils.rs
@@ -42,7 +42,10 @@ where
   let fut: Pin<Box<dyn Future<Output = Result<(), anyhow::Error>>>> =
     async move {
       let listener = TcpListener::bind(options.addr).await?;
-      println!("ready: {}", options.addr);
+      #[allow(clippy::print_stdout)]
+      {
+        println!("ready: {}", options.addr);
+      }
       loop {
         let (stream, _) = listener.accept().await?;
         let io = TokioIo::new(stream);
@@ -58,6 +61,7 @@ where
 
   if let Err(e) = fut.await {
     let err_str = e.to_string();
+    #[allow(clippy::print_stderr)]
     if !err_str.contains("early eof") {
       eprintln!("{}: {:?}", options.error_msg, e);
     }
@@ -89,6 +93,7 @@ pub async fn run_server_with_acceptor<'a, A, F, S>(
 
   if let Err(e) = fut.await {
     let err_str = e.to_string();
+    #[allow(clippy::print_stderr)]
     if !err_str.contains("early eof") {
       eprintln!("{}: {:?}", error_msg, e);
     }
@@ -135,6 +140,7 @@ async fn hyper_serve_connection<I, F, S>(
 
   if let Err(e) = result {
     let err_str = e.to_string();
+    #[allow(clippy::print_stderr)]
     if !err_str.contains("early eof") {
       eprintln!("{}: {:?}", error_msg, e);
     }
diff --git a/tests/util/server/src/servers/mod.rs b/tests/util/server/src/servers/mod.rs
index 3e18aafce4..6c960ce522 100644
--- a/tests/util/server/src/servers/mod.rs
+++ b/tests/util/server/src/servers/mod.rs
@@ -91,6 +91,7 @@ const PROVENANCE_MOCK_SERVER_PORT: u16 = 4251;
 pub(crate) const PUBLIC_NPM_REGISTRY_PORT: u16 = 4260;
 pub(crate) const PRIVATE_NPM_REGISTRY_1_PORT: u16 = 4261;
 pub(crate) const PRIVATE_NPM_REGISTRY_2_PORT: u16 = 4262;
+pub(crate) const PRIVATE_NPM_REGISTRY_3_PORT: u16 = 4263;
 
 // Use the single-threaded scheduler. The hyper server is used as a point of
 // comparison for the (single-threaded!) benchmarks in cli/bench. We're not
@@ -143,6 +144,8 @@ pub async fn run_all_servers() {
     npm_registry::private_npm_registry1(PRIVATE_NPM_REGISTRY_1_PORT);
   let private_npm_registry_2_server_futs =
     npm_registry::private_npm_registry2(PRIVATE_NPM_REGISTRY_2_PORT);
+  let private_npm_registry_3_server_futs =
+    npm_registry::private_npm_registry3(PRIVATE_NPM_REGISTRY_3_PORT);
 
   let mut futures = vec![
     redirect_server_fut.boxed_local(),
@@ -173,6 +176,7 @@ pub async fn run_all_servers() {
   futures.extend(npm_registry_server_futs);
   futures.extend(private_npm_registry_1_server_futs);
   futures.extend(private_npm_registry_2_server_futs);
+  futures.extend(private_npm_registry_3_server_futs);
 
   assert_eq!(futures.len(), TEST_SERVERS_COUNT);
 
@@ -194,7 +198,6 @@ fn json_body(value: serde_json::Value) -> UnsyncBoxBody<Bytes, Infallible> {
 
 /// Benchmark server that just serves "hello world" responses.
 async fn hyper_hello(port: u16) {
-  println!("hyper hello");
   let addr = SocketAddr::from(([127, 0, 0, 1], port));
   let handler = move |_: Request<hyper::body::Incoming>| async move {
     Ok::<_, anyhow::Error>(Response::new(UnsyncBoxBody::new(
@@ -338,7 +341,10 @@ async fn get_tcp_listener_stream(
     .collect::<Vec<_>>();
 
   // Eye catcher for HttpServerCount
-  println!("ready: {name} on {:?}", addresses);
+  #[allow(clippy::print_stdout)]
+  {
+    println!("ready: {name} on {:?}", addresses);
+  }
 
   futures::stream::select_all(listeners)
 }
@@ -354,7 +360,10 @@ async fn run_tls_client_auth_server(port: u16) {
   while let Some(Ok(mut tls_stream)) = tls.next().await {
     tokio::spawn(async move {
       let Ok(handshake) = tls_stream.handshake().await else {
-        eprintln!("Failed to handshake");
+        #[allow(clippy::print_stderr)]
+        {
+          eprintln!("Failed to handshake");
+        }
         return;
       };
       // We only need to check for the presence of client certificates
@@ -401,7 +410,6 @@ async fn absolute_redirect(
       .collect();
 
     if let Some(url) = query_params.get("redirect_to") {
-      println!("URL: {url:?}");
       let redirect = redirect_resp(url.to_owned());
       return Ok(redirect);
     }
@@ -409,7 +417,6 @@ async fn absolute_redirect(
 
   if path.starts_with("/REDIRECT") {
     let url = &req.uri().path()[9..];
-    println!("URL: {url:?}");
     let redirect = redirect_resp(url.to_string());
     return Ok(redirect);
   }
@@ -1353,6 +1360,7 @@ async fn wrap_client_auth_https_server(port: u16) {
       // here. Rusttls ensures that they are valid and signed by the CA.
       match handshake.has_peer_certificates {
         true => { yield Ok(tls); },
+        #[allow(clippy::print_stderr)]
         false => { eprintln!("https_client_auth: no valid client certificate"); },
       };
     }
diff --git a/tests/util/server/src/servers/npm_registry.rs b/tests/util/server/src/servers/npm_registry.rs
index acbd9cab48..4ada468fac 100644
--- a/tests/util/server/src/servers/npm_registry.rs
+++ b/tests/util/server/src/servers/npm_registry.rs
@@ -56,6 +56,14 @@ pub fn private_npm_registry2(port: u16) -> Vec<LocalBoxFuture<'static, ()>> {
   )
 }
 
+pub fn private_npm_registry3(port: u16) -> Vec<LocalBoxFuture<'static, ()>> {
+  run_npm_server(
+    port,
+    "npm private registry server error",
+    private_npm_registry3_handler,
+  )
+}
+
 fn run_npm_server<F, S>(
   port: u16,
   error_msg: &'static str,
@@ -141,6 +149,13 @@ async fn private_npm_registry2_handler(
   handle_req_for_registry(req, &npm::PRIVATE_TEST_NPM_REGISTRY_2).await
 }
 
+async fn private_npm_registry3_handler(
+  req: Request<hyper::body::Incoming>,
+) -> Result<Response<UnsyncBoxBody<Bytes, Infallible>>, anyhow::Error> {
+  // No auth for this registry
+  handle_req_for_registry(req, &npm::PRIVATE_TEST_NPM_REGISTRY_3).await
+}
+
 async fn handle_req_for_registry(
   req: Request<Incoming>,
   test_npm_registry: &npm::TestNpmRegistry,
diff --git a/tests/util/server/src/servers/ws.rs b/tests/util/server/src/servers/ws.rs
index 815119b6a1..dd4efbf659 100644
--- a/tests/util/server/src/servers/ws.rs
+++ b/tests/util/server/src/servers/ws.rs
@@ -76,6 +76,7 @@ pub async fn run_wss2_server(port: u16) {
       let server: Handshake<_, Bytes> = h2.handshake(tls);
       let mut server = match server.await {
         Ok(server) => server,
+        #[allow(clippy::print_stdout)]
         Err(e) => {
           println!("Failed to handshake h2: {e:?}");
           return;
@@ -87,6 +88,7 @@ pub async fn run_wss2_server(port: u16) {
         };
         let (recv, send) = match conn {
           Ok(conn) => conn,
+          #[allow(clippy::print_stdout)]
           Err(e) => {
             println!("Failed to accept a connection: {e:?}");
             break;
@@ -137,6 +139,7 @@ where
           .map_err(|e| anyhow!("Error upgrading websocket connection: {}", e))
           .unwrap();
 
+        #[allow(clippy::print_stderr)]
         if let Err(e) = handler(ws).await {
           eprintln!("Error in websocket connection: {}", e);
         }
@@ -152,6 +155,7 @@ where
       .serve_connection(io, service)
       .with_upgrades();
 
+    #[allow(clippy::print_stderr)]
     if let Err(e) = conn.await {
       eprintln!("websocket server error: {e:?}");
     }
@@ -162,16 +166,19 @@ async fn handle_wss_stream(
   recv: Request<RecvStream>,
   mut send: SendResponse<Bytes>,
 ) -> Result<(), h2::Error> {
+  #[allow(clippy::print_stderr)]
   if recv.method() != Method::CONNECT {
     eprintln!("wss2: refusing non-CONNECT stream");
     send.send_reset(Reason::REFUSED_STREAM);
     return Ok(());
   }
+  #[allow(clippy::print_stderr)]
   let Some(protocol) = recv.extensions().get::<h2::ext::Protocol>() else {
     eprintln!("wss2: refusing no-:protocol stream");
     send.send_reset(Reason::REFUSED_STREAM);
     return Ok(());
   };
+  #[allow(clippy::print_stderr)]
   if protocol.as_str() != "websocket" && protocol.as_str() != "WebSocket" {
     eprintln!("wss2: refusing non-websocket stream");
     send.send_reset(Reason::REFUSED_STREAM);
diff --git a/tools/napi/generate_symbols_lists.js b/tools/napi/generate_symbols_lists.js
index 11cf1c434a..efb0edc043 100755
--- a/tools/napi/generate_symbols_lists.js
+++ b/tools/napi/generate_symbols_lists.js
@@ -1,7 +1,7 @@
 #!/usr/bin/env -S deno run --allow-read --allow-write
 // Copyright 2018-2024 the Deno authors. All rights reserved. MIT license.
 
-import exports from "../../cli/napi/sym/symbol_exports.json" with {
+import exports from "../../ext/napi/sym/symbol_exports.json" with {
   type: "json",
 };
 
@@ -17,7 +17,7 @@ const symbolExportLists = {
 
 for await (const [os, def] of Object.entries(symbolExportLists)) {
   const defUrl = new URL(
-    `../../cli/napi/generated_symbol_exports_list_${os}.def`,
+    `../../ext/napi/generated_symbol_exports_list_${os}.def`,
     import.meta.url,
   );
   await Deno.writeTextFile(defUrl.pathname, def, { create: true });
diff --git a/tools/release/release_doc_template.md b/tools/release/release_doc_template.md
index fec1746bfb..b372185337 100644
--- a/tools/release/release_doc_template.md
+++ b/tools/release/release_doc_template.md
@@ -30,7 +30,7 @@ Release checklist: <LINK TO THIS FORKED GIST GOES HERE>
 
 ## Patch release preparation
 
-**If you are cutting a patch release**: First you need to sync commits to the
+⛔ **If you are cutting a patch release**: First you need to sync commits to the
 `v$MINOR_VERSION` branch in the `deno` repo.
 
 To do that, you need to cherry-pick commits from the main branch to the
@@ -75,13 +75,13 @@ verify on GitHub that everything looks correct.
   1. Click on the "Run workflow" button.
   1. In the drop down, select the minor branch (`v$MINOR_VERSION`) if doing a
      patch release or the main branch if doing a minor release.
-  1. For the kind of release, select either "patch", "minor", or "major".
+  1. For the kind of release, select either `patch` or `minor`.
   1. Run the workflow.
 
 - [ ] Wait for the workflow to complete and for a pull request to be
       automatically opened. Review the pull request, make any necessary changes,
       and merge it.
-  - ⛔ DO NOT create a release tag manually That will automatically happen.
+  - ⛔ **DO NOT** create a release tag manually That will automatically happen.
 
   <details>
      <summary>Failure Steps</summary>
@@ -120,7 +120,8 @@ verify on GitHub that everything looks correct.
   (https://github.com/denoland/deno/releases).
 
 - ⛔ Verify that:
-  - [ ] There are 14 assets on the release draft.
+  - [ ] There are 24 assets on the
+        [GitHub release draft](https://github.com/denoland/deno/releases/v$VERSION).
   - [ ] There are 10 zip files for this version on
         [dl.deno.land](https://console.cloud.google.com/storage/browser/dl.deno.land/release/v$VERSION).