diff --git a/lib/internal/modules/cjs/loader.js b/lib/internal/modules/cjs/loader.js
index 466c160506e..2e0be0e3d8a 100644
--- a/lib/internal/modules/cjs/loader.js
+++ b/lib/internal/modules/cjs/loader.js
@@ -72,7 +72,8 @@ const cjsParseCache = new SafeWeakMap();
 // Set first due to cycle with ESM loader functions.
 module.exports = {
   wrapSafe, Module, toRealPath, readPackageScope, cjsParseCache,
-  get hasLoadedAnyUserCJSModule() { return hasLoadedAnyUserCJSModule; }
+  get hasLoadedAnyUserCJSModule() { return hasLoadedAnyUserCJSModule; },
+  initializeCJS,
 };
 
 const { BuiltinModule } = require('internal/bootstrap/loaders');
@@ -86,8 +87,8 @@ const {
   kEmptyObject,
   filterOwnProperties,
   setOwnProperty,
+  getLazy,
 } = require('internal/util');
-const { Script } = require('vm');
 const { internalCompileFunction } = require('internal/vm');
 const assert = require('internal/assert');
 const fs = require('fs');
@@ -97,21 +98,24 @@ const { sep } = path;
 const { internalModuleStat } = internalBinding('fs');
 const { safeGetenv } = internalBinding('credentials');
 const {
-  cjsConditions,
+  getCjsConditions,
+  initializeCjsConditions,
   hasEsmSyntax,
   loadBuiltinModule,
   makeRequireFunction,
   normalizeReferrerURL,
   stripBOM,
 } = require('internal/modules/helpers');
-const { getOptionValue } = require('internal/options');
-const preserveSymlinks = getOptionValue('--preserve-symlinks');
-const preserveSymlinksMain = getOptionValue('--preserve-symlinks-main');
-const shouldReportRequiredModules = process.env.WATCH_REPORT_DEPENDENCIES;
-// Do not eagerly grab .manifest, it may be in TDZ
-const policy = getOptionValue('--experimental-policy') ?
-  require('internal/process/policy') :
-  null;
+const packageJsonReader = require('internal/modules/package_json_reader');
+const { getOptionValue, getEmbedderOptions } = require('internal/options');
+const policy = getLazy(
+  () => (getOptionValue('--experimental-policy') ? require('internal/process/policy') : null)
+);
+const shouldReportRequiredModules = getLazy(() => process.env.WATCH_REPORT_DEPENDENCIES);
+
+const getCascadedLoader = getLazy(
+  () => require('internal/process/esm_loader').esmLoader
+);
 
 // Whether any user-provided CJS modules had been loaded (executed).
 // Used for internal assertions.
@@ -127,7 +131,6 @@ const {
   setArrowMessage,
 } = require('internal/errors');
 const { validateString } = require('internal/validators');
-const pendingDeprecation = getOptionValue('--pending-deprecation');
 
 const {
   CHAR_BACKWARD_SLASH,
@@ -140,15 +143,7 @@ const {
   isProxy
 } = require('internal/util/types');
 
-const asyncESM = require('internal/process/esm_loader');
-const { enrichCJSError } = require('internal/modules/esm/translators');
 const { kEvaluated } = internalBinding('module_wrap');
-const {
-  encodedSepRegEx,
-  packageExportsResolve,
-  packageImportsResolve
-} = require('internal/modules/esm/resolve');
-
 const isWindows = process.platform === 'win32';
 
 const relativeResolveCache = ObjectCreate(null);
@@ -190,13 +185,13 @@ function updateChildren(parent, child, scan) {
 }
 
 function reportModuleToWatchMode(filename) {
-  if (shouldReportRequiredModules && process.send) {
+  if (shouldReportRequiredModules() && process.send) {
     process.send({ 'watch:require': [filename] });
   }
 }
 
 function reportModuleNotFoundToWatchMode(basePath, extensions) {
-  if (shouldReportRequiredModules && process.send) {
+  if (shouldReportRequiredModules() && process.send) {
     process.send({ 'watch:require': ArrayPrototypeMap(extensions, (ext) => path.resolve(`${basePath}${ext}`)) });
   }
 }
@@ -213,22 +208,6 @@ function Module(id = '', parent) {
   this.children = [];
 }
 
-const builtinModules = [];
-for (const { 0: id, 1: mod } of BuiltinModule.map) {
-  if (mod.canBeRequiredByUsers &&
-    BuiltinModule.canBeRequiredWithoutScheme(id)) {
-    ArrayPrototypePush(builtinModules, id);
-  }
-}
-
-const allBuiltins = new SafeSet(
-  ArrayPrototypeFlatMap(builtinModules, (bm) => [bm, `node:${bm}`])
-);
-BuiltinModule.getSchemeOnlyModuleNames().forEach((builtin) => allBuiltins.add(`node:${builtin}`));
-
-ObjectFreeze(builtinModules);
-Module.builtinModules = builtinModules;
-
 Module._cache = ObjectCreate(null);
 Module._pathCache = ObjectCreate(null);
 Module._extensions = ObjectCreate(null);
@@ -297,26 +276,59 @@ function setModuleParent(value) {
   moduleParentCache.set(this, value);
 }
 
-ObjectDefineProperty(Module.prototype, 'parent', {
-  __proto__: null,
-  get: pendingDeprecation ? deprecate(
-    getModuleParent,
-    'module.parent is deprecated due to accuracy issues. Please use ' +
-      'require.main to find program entry point instead.',
-    'DEP0144'
-  ) : getModuleParent,
-  set: pendingDeprecation ? deprecate(
-    setModuleParent,
-    'module.parent is deprecated due to accuracy issues. Please use ' +
-      'require.main to find program entry point instead.',
-    'DEP0144'
-  ) : setModuleParent,
-});
-
 let debug = require('internal/util/debuglog').debuglog('module', (fn) => {
   debug = fn;
 });
-Module._debug = deprecate(debug, 'Module._debug is deprecated.', 'DEP0077');
+
+const builtinModules = [];
+// This function is called during pre-execution, before any user code is run.
+function initializeCJS() {
+  const pendingDeprecation = getOptionValue('--pending-deprecation');
+  ObjectDefineProperty(Module.prototype, 'parent', {
+    __proto__: null,
+    get: pendingDeprecation ? deprecate(
+      getModuleParent,
+      'module.parent is deprecated due to accuracy issues. Please use ' +
+        'require.main to find program entry point instead.',
+      'DEP0144'
+    ) : getModuleParent,
+    set: pendingDeprecation ? deprecate(
+      setModuleParent,
+      'module.parent is deprecated due to accuracy issues. Please use ' +
+        'require.main to find program entry point instead.',
+      'DEP0144'
+    ) : setModuleParent,
+  });
+  Module._debug = deprecate(debug, 'Module._debug is deprecated.', 'DEP0077');
+
+  for (const { 0: id, 1: mod } of BuiltinModule.map) {
+    if (mod.canBeRequiredByUsers &&
+      BuiltinModule.canBeRequiredWithoutScheme(id)) {
+      ArrayPrototypePush(builtinModules, id);
+    }
+  }
+
+  const allBuiltins = new SafeSet(
+    ArrayPrototypeFlatMap(builtinModules, (bm) => [bm, `node:${bm}`])
+  );
+  BuiltinModule.getSchemeOnlyModuleNames().forEach((builtin) => allBuiltins.add(`node:${builtin}`));
+  ObjectFreeze(builtinModules);
+  Module.builtinModules = builtinModules;
+
+  Module.isBuiltin = function isBuiltin(moduleName) {
+    return allBuiltins.has(moduleName);
+  };
+
+  initializeCjsConditions();
+
+  if (!getEmbedderOptions().noGlobalSearchPaths) {
+    Module._initPaths();
+  }
+
+  // TODO(joyeecheung): deprecate this in favor of a proper hook?
+  Module.runMain =
+    require('internal/modules/run_main').executeUserEntryPoint;
+}
 
 // Given a module name, and a list of paths to test, returns the first
 // matching file in the following precedence.
@@ -337,7 +349,6 @@ function readPackage(requestPath) {
   const existing = packageJsonCache.get(jsonPath);
   if (existing !== undefined) return existing;
 
-  const packageJsonReader = require('internal/modules/package_json_reader');
   const result = packageJsonReader.read(jsonPath);
   const json = result.containsKeys === false ? '{}' : result.string;
   if (json === undefined) {
@@ -440,7 +451,7 @@ const realpathCache = new SafeMap();
 function tryFile(requestPath, isMain) {
   const rc = _stat(requestPath);
   if (rc !== 0) return;
-  if (preserveSymlinks && !isMain) {
+  if (getOptionValue('--preserve-symlinks') && !isMain) {
     return path.resolve(requestPath);
   }
   return toRealPath(requestPath);
@@ -511,9 +522,10 @@ function trySelf(parentPath, request) {
   }
 
   try {
+    const { packageExportsResolve } = require('internal/modules/esm/resolve');
     return finalizeEsmResolution(packageExportsResolve(
       pathToFileURL(pkgPath + '/package.json'), expansion, pkg,
-      pathToFileURL(parentPath), cjsConditions), parentPath, pkgPath);
+      pathToFileURL(parentPath), getCjsConditions()), parentPath, pkgPath);
   } catch (e) {
     if (e.code === 'ERR_MODULE_NOT_FOUND')
       throw createEsmNotFoundErr(request, pkgPath + '/package.json');
@@ -535,9 +547,10 @@ function resolveExports(nmPath, request) {
   const pkg = _readPackage(pkgPath);
   if (pkg?.exports != null) {
     try {
+      const { packageExportsResolve } = require('internal/modules/esm/resolve');
       return finalizeEsmResolution(packageExportsResolve(
         pathToFileURL(pkgPath + '/package.json'), '.' + expansion, pkg, null,
-        cjsConditions), null, pkgPath);
+        getCjsConditions()), null, pkgPath);
     } catch (e) {
       if (e.code === 'ERR_MODULE_NOT_FOUND')
         throw createEsmNotFoundErr(request, pkgPath + '/package.json');
@@ -616,19 +629,19 @@ Module._findPath = function(request, paths, isMain) {
     if (!trailingSlash) {
       if (rc === 0) {  // File.
         if (!isMain) {
-          if (preserveSymlinks) {
+          if (getOptionValue('--preserve-symlinks')) {
             filename = path.resolve(basePath);
           } else {
             filename = toRealPath(basePath);
           }
-        } else if (preserveSymlinksMain) {
-          // For the main module, we use the preserveSymlinksMain flag instead
+        } else if (getOptionValue('--preserve-symlinks-main')) {
+          // For the main module, we use the --preserve-symlinks-main flag instead
           // mainly for backward compatibility, as the preserveSymlinks flag
           // historically has not applied to the main module.  Most likely this
           // was intended to keep .bin/ binaries working, as following those
           // symlinks is usually required for the imports in the corresponding
           // files to resolve; that said, in some use cases following symlinks
-          // causes bigger problems which is why the preserveSymlinksMain option
+          // causes bigger problems which is why the --preserve-symlinks-main option
           // is needed.
           filename = path.resolve(basePath);
         } else {
@@ -999,9 +1012,10 @@ Module._resolveFilename = function(request, parent, isMain, options) {
     const pkg = readPackageScope(parentPath) || {};
     if (pkg.data?.imports != null) {
       try {
+        const { packageImportsResolve } = require('internal/modules/esm/resolve');
         return finalizeEsmResolution(
           packageImportsResolve(request, pathToFileURL(parentPath),
-                                cjsConditions), parentPath,
+                                getCjsConditions()), parentPath,
           pkg.path);
       } catch (e) {
         if (e.code === 'ERR_MODULE_NOT_FOUND')
@@ -1043,6 +1057,7 @@ Module._resolveFilename = function(request, parent, isMain, options) {
 };
 
 function finalizeEsmResolution(resolved, parentPath, pkgPath) {
+  const { encodedSepRegEx } = require('internal/modules/esm/resolve');
   if (RegExpPrototypeExec(encodedSepRegEx, resolved) !== null)
     throw new ERR_INVALID_MODULE_SPECIFIER(
       resolved, 'must not include encoded "/" or "\\" characters', parentPath);
@@ -1081,14 +1096,14 @@ Module.prototype.load = function(filename) {
   Module._extensions[extension](this, filename);
   this.loaded = true;
 
-  const esmLoader = asyncESM.esmLoader;
+  const cascadedLoader = getCascadedLoader();
   // Create module entry at load time to snapshot exports correctly
   const exports = this.exports;
   // Preemptively cache
   if ((module?.module === undefined ||
        module.module.getStatus() < kEvaluated) &&
-      !esmLoader.cjsCache.has(this))
-    esmLoader.cjsCache.set(this, exports);
+      !cascadedLoader.cjsCache.has(this))
+    cascadedLoader.cjsCache.set(this, exports);
 };
 
 
@@ -1113,17 +1128,20 @@ Module.prototype.require = function(id) {
 // (needed for setting breakpoint when called with --inspect-brk)
 let resolvedArgv;
 let hasPausedEntry = false;
-
+let Script;
 function wrapSafe(filename, content, cjsModuleInstance) {
   if (patched) {
     const wrapper = Module.wrap(content);
+    if (Script === undefined) {
+      ({ Script } = require('vm'));
+    }
     const script = new Script(wrapper, {
       filename,
       lineOffset: 0,
       importModuleDynamically: async (specifier, _, importAssertions) => {
-        const loader = asyncESM.esmLoader;
-        return loader.import(specifier, normalizeReferrerURL(filename),
-                             importAssertions);
+        const cascadedLoader = getCascadedLoader();
+        return cascadedLoader.import(specifier, normalizeReferrerURL(filename),
+                                     importAssertions);
       },
     });
 
@@ -1147,9 +1165,9 @@ function wrapSafe(filename, content, cjsModuleInstance) {
     ], {
       filename,
       importModuleDynamically(specifier, _, importAssertions) {
-        const loader = asyncESM.esmLoader;
-        return loader.import(specifier, normalizeReferrerURL(filename),
-                             importAssertions);
+        const cascadedLoader = getCascadedLoader();
+        return cascadedLoader.import(specifier, normalizeReferrerURL(filename),
+                                     importAssertions);
       },
     });
 
@@ -1160,8 +1178,10 @@ function wrapSafe(filename, content, cjsModuleInstance) {
 
     return result.function;
   } catch (err) {
-    if (process.mainModule === cjsModuleInstance)
+    if (process.mainModule === cjsModuleInstance) {
+      const { enrichCJSError } = require('internal/modules/esm/translators');
       enrichCJSError(err, content);
+    }
     throw err;
   }
 }
@@ -1173,10 +1193,11 @@ function wrapSafe(filename, content, cjsModuleInstance) {
 Module.prototype._compile = function(content, filename) {
   let moduleURL;
   let redirects;
-  if (policy?.manifest) {
+  const manifest = policy()?.manifest;
+  if (manifest) {
     moduleURL = pathToFileURL(filename);
-    redirects = policy.manifest.getDependencyMapper(moduleURL);
-    policy.manifest.assertIntegrity(moduleURL, content);
+    redirects = manifest.getDependencyMapper(moduleURL);
+    manifest.assertIntegrity(moduleURL, content);
   }
 
   const compiledWrapper = wrapSafe(filename, content, this);
@@ -1277,9 +1298,10 @@ Module._extensions['.js'] = function(module, filename) {
 Module._extensions['.json'] = function(module, filename) {
   const content = fs.readFileSync(filename, 'utf8');
 
-  if (policy?.manifest) {
+  const manifest = policy()?.manifest;
+  if (manifest) {
     const moduleURL = pathToFileURL(filename);
-    policy.manifest.assertIntegrity(moduleURL, content);
+    manifest.assertIntegrity(moduleURL, content);
   }
 
   try {
@@ -1293,10 +1315,11 @@ Module._extensions['.json'] = function(module, filename) {
 
 // Native extension for .node
 Module._extensions['.node'] = function(module, filename) {
-  if (policy?.manifest) {
+  const manifest = policy()?.manifest;
+  if (manifest) {
     const content = fs.readFileSync(filename);
     const moduleURL = pathToFileURL(filename);
-    policy.manifest.assertIntegrity(moduleURL, content);
+    manifest.assertIntegrity(moduleURL, content);
   }
   // Be aware this doesn't use `content`
   return process.dlopen(module, path.toNamespacedPath(filename));
@@ -1405,9 +1428,5 @@ Module.syncBuiltinESMExports = function syncBuiltinESMExports() {
   }
 };
 
-Module.isBuiltin = function isBuiltin(moduleName) {
-  return allBuiltins.has(moduleName);
-};
-
 // Backwards compatibility
 Module.Module = Module;
diff --git a/lib/internal/modules/helpers.js b/lib/internal/modules/helpers.js
index fea3fbcf48d..49c086279e2 100644
--- a/lib/internal/modules/helpers.js
+++ b/lib/internal/modules/helpers.js
@@ -25,22 +25,31 @@ const { pathToFileURL, fileURLToPath, URL } = require('internal/url');
 
 const { getOptionValue } = require('internal/options');
 const { setOwnProperty } = require('internal/util');
-const userConditions = getOptionValue('--conditions');
 
 let debug = require('internal/util/debuglog').debuglog('module', (fn) => {
   debug = fn;
 });
 
-const noAddons = getOptionValue('--no-addons');
-const addonConditions = noAddons ? [] : ['node-addons'];
+let cjsConditions;
+function initializeCjsConditions() {
+  const userConditions = getOptionValue('--conditions');
+  const noAddons = getOptionValue('--no-addons');
+  const addonConditions = noAddons ? [] : ['node-addons'];
+  // TODO: Use this set when resolving pkg#exports conditions in loader.js.
+  cjsConditions = new SafeSet([
+    'require',
+    'node',
+    ...addonConditions,
+    ...userConditions,
+  ]);
+}
 
-// TODO: Use this set when resolving pkg#exports conditions in loader.js.
-const cjsConditions = new SafeSet([
-  'require',
-  'node',
-  ...addonConditions,
-  ...userConditions,
-]);
+function getCjsConditions() {
+  if (cjsConditions === undefined) {
+    initializeCjsConditions();
+  }
+  return cjsConditions;
+}
 
 function loadBuiltinModule(filename, request) {
   const mod = BuiltinModule.map.get(filename);
@@ -62,7 +71,7 @@ function makeRequireFunction(mod, redirects) {
   let require;
   if (redirects) {
     const id = mod.filename || mod.id;
-    const conditions = cjsConditions;
+    const conditions = getCjsConditions();
     const { resolve, reaction } = redirects;
     require = function require(specifier) {
       let missing = true;
@@ -231,7 +240,8 @@ function hasEsmSyntax(code) {
 
 module.exports = {
   addBuiltinLibsToObject,
-  cjsConditions,
+  getCjsConditions,
+  initializeCjsConditions,
   hasEsmSyntax,
   loadBuiltinModule,
   makeRequireFunction,
diff --git a/lib/internal/process/pre_execution.js b/lib/internal/process/pre_execution.js
index 899a69a6f3b..d66a699b14c 100644
--- a/lib/internal/process/pre_execution.js
+++ b/lib/internal/process/pre_execution.js
@@ -560,13 +560,8 @@ function initializeWASI() {
 }
 
 function initializeCJSLoader() {
-  const CJSLoader = require('internal/modules/cjs/loader');
-  if (!getEmbedderOptions().noGlobalSearchPaths) {
-    CJSLoader.Module._initPaths();
-  }
-  // TODO(joyeecheung): deprecate this in favor of a proper hook?
-  CJSLoader.Module.runMain =
-    require('internal/modules/run_main').executeUserEntryPoint;
+  const { initializeCJS } = require('internal/modules/cjs/loader');
+  initializeCJS();
 }
 
 function initializeESMLoader() {
diff --git a/test/fixtures/inspector-global-function.js b/test/fixtures/inspector-global-function.mjs
similarity index 100%
rename from test/fixtures/inspector-global-function.js
rename to test/fixtures/inspector-global-function.mjs
diff --git a/test/parallel/test-bootstrap-modules.js b/test/parallel/test-bootstrap-modules.js
index 3ecc7f91a64..10513e796db 100644
--- a/test/parallel/test-bootstrap-modules.js
+++ b/test/parallel/test-bootstrap-modules.js
@@ -53,26 +53,15 @@ const expectedModules = new Set([
   'NativeModule internal/fs/utils',
   'NativeModule internal/idna',
   'NativeModule internal/linkedlist',
-  'NativeModule internal/modules/helpers',
   'NativeModule internal/modules/cjs/loader',
-  'NativeModule internal/modules/esm/assert',
-  'NativeModule internal/modules/esm/formats',
-  'NativeModule internal/modules/esm/get_format',
-  'NativeModule internal/modules/esm/initialize_import_meta',
-  'NativeModule internal/modules/esm/load',
-  'NativeModule internal/modules/esm/loader',
-  'NativeModule internal/modules/esm/module_map',
-  'NativeModule internal/modules/esm/package_config',
-  'NativeModule internal/modules/esm/resolve',
-  'NativeModule internal/modules/esm/translators',
   'NativeModule internal/modules/esm/utils',
+  'NativeModule internal/modules/helpers',
   'NativeModule internal/modules/package_json_reader',
   'NativeModule internal/modules/run_main',
   'NativeModule internal/net',
   'NativeModule internal/options',
   'NativeModule internal/perf/utils',
   'NativeModule internal/priority_queue',
-  'NativeModule internal/process/esm_loader',
   'NativeModule internal/process/execution',
   'NativeModule internal/process/per_thread',
   'NativeModule internal/process/pre_execution',
@@ -100,15 +89,10 @@ const expectedModules = new Set([
   'NativeModule timers',
   'NativeModule url',
   'NativeModule util',
-  'NativeModule vm',
 ]);
 
 if (!common.isMainThread) {
   [
-    'Internal Binding messaging',
-    'Internal Binding performance',
-    'Internal Binding symbols',
-    'Internal Binding worker',
     'NativeModule diagnostics_channel',
     'NativeModule internal/abort_controller',
     'NativeModule internal/error_serdes',
@@ -139,6 +123,11 @@ if (!common.isMainThread) {
   ].forEach(expectedModules.add.bind(expectedModules));
 }
 
+if (common.isWindows) {
+  // On Windows fs needs SideEffectFreeRegExpPrototypeExec which uses vm.
+  expectedModules.add('NativeModule vm');
+}
+
 if (common.hasIntl) {
   expectedModules.add('Internal Binding icu');
 } else {
diff --git a/test/sequential/test-inspector-break-when-eval.js b/test/sequential/test-inspector-break-when-eval.js
index 1e7ab513dad..bd9969e0dcf 100644
--- a/test/sequential/test-inspector-break-when-eval.js
+++ b/test/sequential/test-inspector-break-when-eval.js
@@ -6,7 +6,10 @@ const { NodeInstance } = require('../common/inspector-helper.js');
 const fixtures = require('../common/fixtures');
 const { pathToFileURL } = require('url');
 
-const script = fixtures.path('inspector-global-function.js');
+// This needs to be an ES module file to ensure that internal modules are
+// loaded before pausing. See
+// https://bugs.chromium.org/p/chromium/issues/detail?id=1246905
+const script = fixtures.path('inspector-global-function.mjs');
 
 async function setupDebugger(session) {
   console.log('[test]', 'Setting up a debugger');
@@ -23,7 +26,7 @@ async function setupDebugger(session) {
 
   // NOTE(mmarchini): We wait for the second console.log to ensure we loaded
   // every internal module before pausing. See
-  // https://bugs.chromium.org/p/v8/issues/detail?id=10287.
+  // https://bugs.chromium.org/p/chromium/issues/detail?id=1246905
   const waitForReady = session.waitForConsoleOutput('log', 'Ready!');
   session.send({ 'method': 'Debugger.resume' });
   await waitForReady;