diff --git a/lib/internal/modules/cjs/loader.js b/lib/internal/modules/cjs/loader.js
index 3b16099848a3a9..57470fb90dd907 100644
--- a/lib/internal/modules/cjs/loader.js
+++ b/lib/internal/modules/cjs/loader.js
@@ -69,7 +69,8 @@ const {
     module_export_names_private_symbol,
     module_circular_visited_private_symbol,
     module_export_private_symbol,
-    module_parent_private_symbol,
+    module_first_parent_private_symbol,
+    module_last_parent_private_symbol,
   },
   isInsideNodeModules,
 } = internalBinding('util');
@@ -94,9 +95,13 @@ const kModuleCircularVisited = module_circular_visited_private_symbol;
  */
 const kModuleExport = module_export_private_symbol;
 /**
- * {@link Module} parent module.
+ * {@link Module} The first parent module that loads a module with require().
  */
-const kModuleParent = module_parent_private_symbol;
+const kFirstModuleParent = module_first_parent_private_symbol;
+/**
+ * {@link Module} The last parent module that loads a module with require().
+ */
+const kLastModuleParent = module_last_parent_private_symbol;
 
 const kIsMainSymbol = Symbol('kIsMainSymbol');
 const kIsCachedByESMLoader = Symbol('kIsCachedByESMLoader');
@@ -117,6 +122,7 @@ module.exports = {
   findLongestRegisteredExtension,
   resolveForCJSWithHooks,
   loadSourceForCJSWithHooks: loadSource,
+  populateCJSExportsFromESM,
   wrapSafe,
   wrapModuleLoad,
   kIsMainSymbol,
@@ -326,7 +332,8 @@ function Module(id = '', parent) {
   this.id = id;
   this.path = path.dirname(id);
   setOwnProperty(this, 'exports', {});
-  this[kModuleParent] = parent;
+  this[kFirstModuleParent] = parent;
+  this[kLastModuleParent] = parent;
   updateChildren(parent, this, false);
   this.filename = null;
   this.loaded = false;
@@ -408,7 +415,7 @@ ObjectDefineProperty(BuiltinModule.prototype, 'isPreloading', isPreloadingDesc);
  * @returns {object}
  */
 function getModuleParent() {
-  return this[kModuleParent];
+  return this[kFirstModuleParent];
 }
 
 /**
@@ -418,7 +425,7 @@ function getModuleParent() {
  * @returns {void}
  */
 function setModuleParent(value) {
-  this[kModuleParent] = value;
+  this[kFirstModuleParent] = value;
 }
 
 let debug = debuglog('module', (fn) => {
@@ -997,7 +1004,7 @@ function getExportsForCircularRequire(module) {
   const requiredESM = module[kRequiredModuleSymbol];
   if (requiredESM && requiredESM.getStatus() !== kEvaluated) {
     let message = `Cannot require() ES Module ${module.id} in a cycle.`;
-    const parent = module[kModuleParent];
+    const parent = module[kLastModuleParent];
     if (parent) {
       message += ` (from ${parent.filename})`;
     }
@@ -1278,6 +1285,8 @@ Module._load = function(request, parent, isMain) {
     // load hooks for the module keyed by the (potentially customized) filename.
     module[kURL] = url;
     module[kFormat] = format;
+  } else {
+    module[kLastModuleParent] = parent;
   }
 
   if (parent !== undefined) {
@@ -1397,7 +1406,8 @@ Module._resolveFilename = function(request, parent, isMain, options) {
   const requireStack = [];
   for (let cursor = parent;
     cursor;
-    cursor = cursor[kModuleParent]) {
+    // TODO(joyeecheung): it makes more sense to use kLastModuleParent here.
+    cursor = cursor[kFirstModuleParent]) {
     ArrayPrototypePush(requireStack, cursor.filename || cursor.id);
   }
   let message = `Cannot find module '${request}'`;
@@ -1514,7 +1524,7 @@ function loadESMFromCJS(mod, filename, format, source) {
     // ESM won't be accessible via process.mainModule.
     setOwnProperty(process, 'mainModule', undefined);
   } else {
-    const parent = mod[kModuleParent];
+    const parent = mod[kLastModuleParent];
 
     requireModuleWarningMode ??= getOptionValue('--trace-require-module');
     if (requireModuleWarningMode) {
@@ -1564,54 +1574,66 @@ function loadESMFromCJS(mod, filename, format, source) {
       wrap,
       namespace,
     } = cascadedLoader.importSyncForRequire(mod, filename, source, isMain, parent);
-    // Tooling in the ecosystem have been using the __esModule property to recognize
-    // transpiled ESM in consuming code. For example, a 'log' package written in ESM:
-    //
-    // export default function log(val) { console.log(val); }
-    //
-    // Can be transpiled as:
-    //
-    // exports.__esModule = true;
-    // exports.default = function log(val) { console.log(val); }
-    //
-    // The consuming code may be written like this in ESM:
-    //
-    // import log from 'log'
-    //
-    // Which gets transpiled to:
-    //
-    // const _mod = require('log');
-    // const log = _mod.__esModule ? _mod.default : _mod;
-    //
-    // So to allow transpiled consuming code to recognize require()'d real ESM
-    // as ESM and pick up the default exports, we add a __esModule property by
-    // building a source text module facade for any module that has a default
-    // export and add .__esModule = true to the exports. This maintains the
-    // enumerability of the re-exported names and the live binding of the exports,
-    // without incurring a non-trivial per-access overhead on the exports.
-    //
-    // The source of the facade is defined as a constant per-isolate property
-    // required_module_default_facade_source_string, which looks like this
-    //
-    // export * from 'original';
-    // export { default } from 'original';
-    // export const __esModule = true;
-    //
-    // And the 'original' module request is always resolved by
-    // createRequiredModuleFacade() to `wrap` which is a ModuleWrap wrapping
-    // over the original module.
-
-    // We don't do this to modules that are marked as CJS ESM or that
-    // don't have default exports to avoid the unnecessary overhead.
-    // If __esModule is already defined, we will also skip the extension
-    // to allow users to override it.
-    if (ObjectHasOwn(namespace, 'module.exports')) {
-      mod.exports = namespace['module.exports'];
-    } else if (!ObjectHasOwn(namespace, 'default') || ObjectHasOwn(namespace, '__esModule')) {
-      mod.exports = namespace;
-    } else {
-      mod.exports = createRequiredModuleFacade(wrap);
-    }
+
+    populateCJSExportsFromESM(mod, wrap, namespace);
+  }
+}
+
+/**
+ * Populate the exports of a CJS module entry from an ESM module's namespace object for
+ * require(esm).
+ * @param {Module} mod CJS module instance
+ * @param {ModuleWrap} wrap ESM ModuleWrap instance.
+ * @param {object} namespace The ESM namespace object.
+ */
+function populateCJSExportsFromESM(mod, wrap, namespace) {
+  // Tooling in the ecosystem have been using the __esModule property to recognize
+  // transpiled ESM in consuming code. For example, a 'log' package written in ESM:
+  //
+  // export default function log(val) { console.log(val); }
+  //
+  // Can be transpiled as:
+  //
+  // exports.__esModule = true;
+  // exports.default = function log(val) { console.log(val); }
+  //
+  // The consuming code may be written like this in ESM:
+  //
+  // import log from 'log'
+  //
+  // Which gets transpiled to:
+  //
+  // const _mod = require('log');
+  // const log = _mod.__esModule ? _mod.default : _mod;
+  //
+  // So to allow transpiled consuming code to recognize require()'d real ESM
+  // as ESM and pick up the default exports, we add a __esModule property by
+  // building a source text module facade for any module that has a default
+  // export and add .__esModule = true to the exports. This maintains the
+  // enumerability of the re-exported names and the live binding of the exports,
+  // without incurring a non-trivial per-access overhead on the exports.
+  //
+  // The source of the facade is defined as a constant per-isolate property
+  // required_module_default_facade_source_string, which looks like this
+  //
+  // export * from 'original';
+  // export { default } from 'original';
+  // export const __esModule = true;
+  //
+  // And the 'original' module request is always resolved by
+  // createRequiredModuleFacade() to `wrap` which is a ModuleWrap wrapping
+  // over the original module.
+
+  // We don't do this to modules that are marked as CJS ESM or that
+  // don't have default exports to avoid the unnecessary overhead.
+  // If __esModule is already defined, we will also skip the extension
+  // to allow users to override it.
+  if (ObjectHasOwn(namespace, 'module.exports')) {
+    mod.exports = namespace['module.exports'];
+  } else if (!ObjectHasOwn(namespace, 'default') || ObjectHasOwn(namespace, '__esModule')) {
+    mod.exports = namespace;
+  } else {
+    mod.exports = createRequiredModuleFacade(wrap);
   }
 }
 
@@ -1804,7 +1826,7 @@ function reconstructErrorStack(err, parentPath, parentSource) {
  */
 function getRequireESMError(mod, pkg, content, filename) {
   // This is an error path because `require` of a `.js` file in a `"type": "module"` scope is not allowed.
-  const parent = mod[kModuleParent];
+  const parent = mod[kFirstModuleParent];
   const parentPath = parent?.filename;
   const packageJsonPath = pkg?.path;
   const usesEsm = containsModuleSyntax(content, filename);
diff --git a/lib/internal/modules/esm/loader.js b/lib/internal/modules/esm/loader.js
index 0443838c8a4ba5..149151ec120b5a 100644
--- a/lib/internal/modules/esm/loader.js
+++ b/lib/internal/modules/esm/loader.js
@@ -17,6 +17,7 @@ const {
 const {
   kIsExecuting,
   kRequiredModuleSymbol,
+  Module: CJSModule,
 } = require('internal/modules/cjs/loader');
 const { imported_cjs_symbol } = internalBinding('symbols');
 
@@ -91,13 +92,18 @@ function newLoadCache() {
   return new LoadCache();
 }
 
+let _translators;
+function lazyLoadTranslators() {
+  _translators ??= require('internal/modules/esm/translators');
+  return _translators;
+}
+
 /**
  * Lazy-load translators to avoid potentially unnecessary work at startup (ex if ESM is not used).
  * @returns {import('./translators.js').Translators}
  */
 function getTranslators() {
-  const { translators } = require('internal/modules/esm/translators');
-  return translators;
+  return lazyLoadTranslators().translators;
 }
 
 /**
@@ -506,7 +512,7 @@ class ModuleLoader {
 
     const { source } = loadResult;
     const isMain = (parentURL === undefined);
-    const wrap = this.#translate(url, finalFormat, source, isMain);
+    const wrap = this.#translate(url, finalFormat, source, parentURL);
     assert(wrap instanceof ModuleWrap, `Translator used for require(${url}) should not be async`);
 
     if (process.env.WATCH_REPORT_DEPENDENCIES && process.send) {
@@ -542,10 +548,10 @@ class ModuleLoader {
    * @param {string} format Format of the module to be translated. This is used to find
    *   matching translators.
    * @param {ModuleSource} source Source of the module to be translated.
-   * @param {boolean} isMain Whether the module to be translated is the entry point.
+   * @param {string|undefined} parentURL URL of the parent module. Undefined if it's the entry point.
    * @returns {ModuleWrap}
    */
-  #translate(url, format, source, isMain) {
+  #translate(url, format, source, parentURL) {
     this.validateLoadResult(url, format);
     const translator = getTranslators().get(format);
 
@@ -553,7 +559,20 @@ class ModuleLoader {
       throw new ERR_UNKNOWN_MODULE_FORMAT(format, url);
     }
 
-    const result = FunctionPrototypeCall(translator, this, url, source, isMain);
+    // Populate the CJS cache with a facade for ESM in case subsequent require(esm) is
+    // looking it up from the cache. The parent module of the CJS cache entry would be the
+    // first CJS module that loads it with require(). This is an approximation, because
+    // ESM caches more and it does not get re-loaded and updated every time an `import` is
+    // encountered, unlike CJS require(), and we only use the parent entry to provide
+    // more information in error messages.
+    if (format === 'module') {
+      const parentFilename = urlToFilename(parentURL);
+      const parent = parentFilename ? CJSModule._cache[parentFilename] : undefined;
+      const cjsModule = lazyLoadTranslators().cjsEmplaceModuleCacheEntryForURL(url, parent);
+      debug('cjsEmplaceModuleCacheEntryForURL', url, parent, cjsModule);
+    }
+
+    const result = FunctionPrototypeCall(translator, this, url, source, parentURL === undefined);
     assert(result instanceof ModuleWrap);
     return result;
   }
@@ -563,10 +582,10 @@ class ModuleLoader {
    * This is run synchronously, and the translator always return a ModuleWrap synchronously.
    * @param {string} url URL of the module to be translated.
    * @param {object} loadContext See {@link load}
-   * @param {boolean} isMain Whether the module to be translated is the entry point.
+   * @param {string|undefined} parentURL URL of the parent module. Undefined if it's the entry point.
    * @returns {ModuleWrap}
    */
-  loadAndTranslateForRequireInImportedCJS(url, loadContext, isMain) {
+  loadAndTranslateForRequireInImportedCJS(url, loadContext, parentURL) {
     const { format: formatFromLoad, source } = this.#loadSync(url, loadContext);
 
     if (formatFromLoad === 'wasm') {  // require(wasm) is not supported.
@@ -587,7 +606,7 @@ class ModuleLoader {
       finalFormat = 'require-commonjs-typescript';
     }
 
-    const wrap = this.#translate(url, finalFormat, source, isMain);
+    const wrap = this.#translate(url, finalFormat, source, parentURL);
     assert(wrap instanceof ModuleWrap, `Translator used for require(${url}) should not be async`);
     return wrap;
   }
@@ -597,13 +616,13 @@ class ModuleLoader {
    * This may be run asynchronously if there are asynchronous module loader hooks registered.
    * @param {string} url URL of the module to be translated.
    * @param {object} loadContext See {@link load}
-   * @param {boolean} isMain Whether the module to be translated is the entry point.
+   * @param {string|undefined} parentURL URL of the parent module. Undefined if it's the entry point.
    * @returns {Promise<ModuleWrap>|ModuleWrap}
    */
-  loadAndTranslate(url, loadContext, isMain) {
+  loadAndTranslate(url, loadContext, parentURL) {
     const maybePromise = this.load(url, loadContext);
     const afterLoad = ({ format, source }) => {
-      return this.#translate(url, format, source, isMain);
+      return this.#translate(url, format, source, parentURL);
     };
     if (isPromise(maybePromise)) {
       return maybePromise.then(afterLoad);
@@ -630,9 +649,9 @@ class ModuleLoader {
     const isMain = parentURL === undefined;
     let moduleOrModulePromise;
     if (isForRequireInImportedCJS) {
-      moduleOrModulePromise = this.loadAndTranslateForRequireInImportedCJS(url, context, isMain);
+      moduleOrModulePromise = this.loadAndTranslateForRequireInImportedCJS(url, context, parentURL);
     } else {
-      moduleOrModulePromise = this.loadAndTranslate(url, context, isMain);
+      moduleOrModulePromise = this.loadAndTranslate(url, context, parentURL);
     }
 
     const inspectBrk = (
diff --git a/lib/internal/modules/esm/translators.js b/lib/internal/modules/esm/translators.js
index 98bdb384269ced..7c8e20caf0182c 100644
--- a/lib/internal/modules/esm/translators.js
+++ b/lib/internal/modules/esm/translators.js
@@ -44,6 +44,7 @@ const {
   findLongestRegisteredExtension,
   resolveForCJSWithHooks,
   loadSourceForCJSWithHooks,
+  populateCJSExportsFromESM,
 } = require('internal/modules/cjs/loader');
 const { fileURLToPath, pathToFileURL, URL } = require('internal/url');
 let debug = require('internal/util/debuglog').debuglog('esm', (fn) => {
@@ -148,9 +149,19 @@ function loadCJSModule(module, source, url, filename, isMain) {
       }
       specifier = `${pathToFileURL(path)}`;
     }
+
+    // FIXME(node:59666) Currently, the ESM loader re-invents require() here for imported CJS and this
+    // requires a separate cache to be populated as well as introducing several quirks. This is not ideal.
     const job = cascadedLoader.getModuleJobForRequireInImportedCJS(specifier, url, importAttributes);
     job.runSync();
-    return cjsCache.get(job.url).exports;
+    const mod = cjsCache.get(job.url);
+    assert(mod, `Imported CJS module ${url} failed to load module ${job.url} using require()`);
+    if (!job.module.synthetic && !mod.loaded) {
+      debug('populateCJSExportsFromESM from require(esm) in imported CJS', url, mod, job.module);
+      populateCJSExportsFromESM(mod, job.module, job.module.getNamespace());
+      mod.loaded = true;
+    }
+    return mod.exports;
   };
   setOwnProperty(requireFn, 'resolve', function resolve(specifier) {
     if (!StringPrototypeStartsWith(specifier, 'node:')) {
@@ -171,6 +182,7 @@ function loadCJSModule(module, source, url, filename, isMain) {
 
 // TODO: can we use a weak map instead?
 const cjsCache = new SafeMap();
+
 /**
  * Creates a ModuleWrap object for a CommonJS module.
  * @param {string} url - The URL of the module.
@@ -329,16 +341,17 @@ translators.set('commonjs', function commonjsStrategy(url, source, isMain) {
 /**
  * Get or create an entry in the CJS module cache for the given filename.
  * @param {string} filename CJS module filename
+ * @param {CJSModule} parent The parent CJS module
  * @returns {CJSModule} the cached CJS module entry
  */
-function cjsEmplaceModuleCacheEntry(filename, exportNames) {
+function cjsEmplaceModuleCacheEntry(filename, parent) {
   // TODO: Do we want to keep hitting the user mutable CJS loader here?
   let cjsMod = CJSModule._cache[filename];
   if (cjsMod) {
     return cjsMod;
   }
 
-  cjsMod = new CJSModule(filename);
+  cjsMod = new CJSModule(filename, parent);
   cjsMod.filename = filename;
   cjsMod.paths = CJSModule._nodeModulePaths(cjsMod.path);
   cjsMod[kIsCachedByESMLoader] = true;
@@ -347,6 +360,22 @@ function cjsEmplaceModuleCacheEntry(filename, exportNames) {
   return cjsMod;
 }
 
+/**
+ * Emplace a CJS module cache entry for the given URL.
+ * @param {string} url The module URL
+ * @param {CJSModule} parent The parent CJS module
+ * @returns {CJSModule|undefined} the cached CJS module entry, undefined if url cannot be used to identify a CJS entry.
+ */
+exports.cjsEmplaceModuleCacheEntryForURL = function cjsEmplaceModuleCacheEntryForURL(url, parent) {
+  const filename = urlToFilename(url);
+  if (!filename) {
+    return;
+  }
+  const cjsModule = cjsEmplaceModuleCacheEntry(filename, parent);
+  cjsCache.set(url, cjsModule);
+  return cjsModule;
+};
+
 /**
  * Pre-parses a CommonJS module's exports and re-exports.
  * @param {string} filename - The filename of the module.
diff --git a/lib/internal/modules/helpers.js b/lib/internal/modules/helpers.js
index 9a47dc92d9ce9d..9f66578a459e7c 100644
--- a/lib/internal/modules/helpers.js
+++ b/lib/internal/modules/helpers.js
@@ -22,7 +22,7 @@ const { validateString } = require('internal/validators');
 const fs = require('fs'); // Import all of `fs` so that it can be monkey-patched.
 const internalFS = require('internal/fs/utils');
 const path = require('path');
-const { pathToFileURL, fileURLToPath } = require('internal/url');
+const { pathToFileURL, fileURLToPath, URL } = require('internal/url');
 const assert = require('internal/assert');
 
 const { getOptionValue } = require('internal/options');
@@ -295,13 +295,32 @@ function normalizeReferrerURL(referrerName) {
 }
 
 /**
+ * Coerce a URL string to a filename. This is used by the ESM loader
+ * to map ESM URLs to entries in the CJS module cache on a best-effort basis.
+ * TODO(joyeecheung): this can be rather expensive, cache the result on the
+ * ModuleWrap wherever we can.
  * @param {string|undefined} url URL to convert to filename
  * @returns {string|undefined}
  */
 function urlToFilename(url) {
   if (url && StringPrototypeStartsWith(url, 'file://')) {
-    return fileURLToPath(url);
+    let urlObj;
+    try {
+      urlObj = new URL(url);
+    } catch {
+      // Not a proper URL, return as-is as the cache key.
+      return url;
+    }
+    try {
+      return fileURLToPath(urlObj);
+    } catch {
+      // This is generally only possible when the URL is provided by a custom loader.
+      // Just use the path and ignore whether it's absolute or not as there's no such
+      // requirement for CJS cache.
+      return urlObj.pathname;
+    }
   }
+  // Not a file URL, return as-is.
   return url;
 }
 
diff --git a/src/env_properties.h b/src/env_properties.h
index 945f4ffae4d97a..0b0ea5846618af 100644
--- a/src/env_properties.h
+++ b/src/env_properties.h
@@ -30,7 +30,8 @@
   V(module_export_names_private_symbol, "node:module_export_names")            \
   V(module_circular_visited_private_symbol, "node:module_circular_visited")    \
   V(module_export_private_symbol, "node:module_export")                        \
-  V(module_parent_private_symbol, "node:module_parent")                        \
+  V(module_first_parent_private_symbol, "node:module_first_parent")            \
+  V(module_last_parent_private_symbol, "node:module_last_parent")              \
   V(napi_type_tag, "node:napi:type_tag")                                       \
   V(napi_wrapper, "node:napi:wrapper")                                         \
   V(untransferable_object_private_symbol, "node:untransferableObject")         \
@@ -408,6 +409,7 @@
   V(stream_count_string, "streamCount")                                        \
   V(subject_string, "subject")                                                 \
   V(subjectaltname_string, "subjectaltname")                                   \
+  V(synthetic_string, "synthetic")                                             \
   V(syscall_string, "syscall")                                                 \
   V(table_string, "table")                                                     \
   V(target_string, "target")                                                   \
diff --git a/src/module_wrap.cc b/src/module_wrap.cc
index 72d910fa4a8144..06dca66c7641a8 100644
--- a/src/module_wrap.cc
+++ b/src/module_wrap.cc
@@ -22,6 +22,7 @@ using errors::TryCatchScope;
 using node::contextify::ContextifyContext;
 using v8::Array;
 using v8::ArrayBufferView;
+using v8::Boolean;
 using v8::Context;
 using v8::Data;
 using v8::EscapableHandleScope;
@@ -411,6 +412,13 @@ void ModuleWrap::New(const FunctionCallbackInfo<Value>& args) {
     }
   }
 
+  if (that->Set(context,
+                realm->isolate_data()->synthetic_string(),
+                Boolean::New(isolate, synthetic))
+          .IsNothing()) {
+    return;
+  }
+
   if (!that->Set(context, realm->isolate_data()->url_string(), url)
            .FromMaybe(false)) {
     return;
diff --git a/test/es-module/test-require-esm-from-imported-cjs.js b/test/es-module/test-require-esm-from-imported-cjs.js
new file mode 100644
index 00000000000000..b03b41beb1208e
--- /dev/null
+++ b/test/es-module/test-require-esm-from-imported-cjs.js
@@ -0,0 +1,36 @@
+'use strict';
+
+// This tests that the require(esm) works from an imported CJS module
+// when the require-d ESM is cached separately.
+
+require('../common');
+const { spawnSyncAndAssert } = require('../common/child_process');
+const fixtures = require('../common/fixtures');
+
+spawnSyncAndAssert(
+  process.execPath,
+  [
+    '--experimental-require-module',
+    '--import',
+    fixtures.fileURL('es-modules', 'require-esm-in-cjs-cache', 'instrument-sync.js'),
+    fixtures.path('es-modules', 'require-esm-in-cjs-cache', 'app.cjs'),
+  ],
+  {
+    trim: true,
+    stdout: / default: { hello: 'world' }/
+  }
+);
+
+spawnSyncAndAssert(
+  process.execPath,
+  [
+    '--experimental-require-module',
+    '--import',
+    fixtures.fileURL('es-modules', 'require-esm-in-cjs-cache', 'instrument.js'),
+    fixtures.path('es-modules', 'require-esm-in-cjs-cache', 'app.cjs'),
+  ],
+  {
+    trim: true,
+    stdout: / default: { hello: 'world' }/
+  }
+);
diff --git a/test/fixtures/es-modules/require-esm-in-cjs-cache/app.cjs b/test/fixtures/es-modules/require-esm-in-cjs-cache/app.cjs
new file mode 100644
index 00000000000000..66a9fdfe61a623
--- /dev/null
+++ b/test/fixtures/es-modules/require-esm-in-cjs-cache/app.cjs
@@ -0,0 +1 @@
+console.log(require('./test.js'));
diff --git a/test/fixtures/es-modules/require-esm-in-cjs-cache/hooks.js b/test/fixtures/es-modules/require-esm-in-cjs-cache/hooks.js
new file mode 100644
index 00000000000000..f33a40fba77319
--- /dev/null
+++ b/test/fixtures/es-modules/require-esm-in-cjs-cache/hooks.js
@@ -0,0 +1,12 @@
+import { readFileSync } from 'node:fs';
+import { fileURLToPath } from 'node:url';
+
+export async function load(url, context, nextLoad) {
+  const result = await nextLoad(url, context);
+
+  if (result.format === 'commonjs' && !result.source) {
+    result.source = readFileSync(fileURLToPath(url), 'utf8');
+  }
+
+  return result;
+}
diff --git a/test/fixtures/es-modules/require-esm-in-cjs-cache/instrument-sync.js b/test/fixtures/es-modules/require-esm-in-cjs-cache/instrument-sync.js
new file mode 100644
index 00000000000000..99d3a6608e028e
--- /dev/null
+++ b/test/fixtures/es-modules/require-esm-in-cjs-cache/instrument-sync.js
@@ -0,0 +1,7 @@
+import * as mod from 'node:module';
+
+mod.registerHooks({
+  load(url, context, nextLoad) {
+    return nextLoad(url, context);
+  },
+});
diff --git a/test/fixtures/es-modules/require-esm-in-cjs-cache/instrument.js b/test/fixtures/es-modules/require-esm-in-cjs-cache/instrument.js
new file mode 100644
index 00000000000000..1c99b7e9c759c9
--- /dev/null
+++ b/test/fixtures/es-modules/require-esm-in-cjs-cache/instrument.js
@@ -0,0 +1,3 @@
+import * as mod from 'node:module';
+
+mod.register(new URL('hooks.js', import.meta.url).toString());
diff --git a/test/fixtures/es-modules/require-esm-in-cjs-cache/package.json b/test/fixtures/es-modules/require-esm-in-cjs-cache/package.json
new file mode 100644
index 00000000000000..3dbc1ca591c055
--- /dev/null
+++ b/test/fixtures/es-modules/require-esm-in-cjs-cache/package.json
@@ -0,0 +1,3 @@
+{
+  "type": "module"
+}
diff --git a/test/fixtures/es-modules/require-esm-in-cjs-cache/test.js b/test/fixtures/es-modules/require-esm-in-cjs-cache/test.js
new file mode 100644
index 00000000000000..64dc1e8aaabff4
--- /dev/null
+++ b/test/fixtures/es-modules/require-esm-in-cjs-cache/test.js
@@ -0,0 +1 @@
+export default { hello: 'world' };