diff --git a/lib/internal/modules/cjs/loader.js b/lib/internal/modules/cjs/loader.js
index e420a10e4867a1..b636f39041a5fc 100644
--- a/lib/internal/modules/cjs/loader.js
+++ b/lib/internal/modules/cjs/loader.js
@@ -612,8 +612,12 @@ Module._resolveFilename = function(request, parent, isMain, options) {
       cursor = cursor.parent) {
       requireStack.push(cursor.filename || cursor.id);
     }
+    let message = `Cannot find module '${request}'`;
+    if (requireStack.length > 0) {
+      message = message + '\nRequire stack:\n- ' + requireStack.join('\n- ');
+    }
     // eslint-disable-next-line no-restricted-syntax
-    var err = new Error(`Cannot find module '${request}'`);
+    var err = new Error(message);
     err.code = 'MODULE_NOT_FOUND';
     err.requireStack = requireStack;
     throw err;
diff --git a/test/fixtures/require-resolve.js b/test/fixtures/require-resolve.js
index 2a0dc8846ce3cb..aa496e5eb66f70 100644
--- a/test/fixtures/require-resolve.js
+++ b/test/fixtures/require-resolve.js
@@ -15,21 +15,21 @@ assert.strictEqual(
 // Verify that existing paths are removed.
 assert.throws(() => {
   require.resolve('bar', { paths: [] })
-}, /^Error: Cannot find module 'bar'$/);
+}, /^Error: Cannot find module 'bar'/);
 
 // Verify that resolution path can be overwritten.
 {
   // three.js cannot be loaded from this file by default.
   assert.throws(() => {
     require.resolve('three')
-  }, /^Error: Cannot find module 'three'$/);
+  }, /^Error: Cannot find module 'three'/);
 
   // If the nested-index directory is provided as a resolve path, 'three'
   // cannot be found because nested-index is used as a starting point and not
   // a searched directory.
   assert.throws(() => {
     require.resolve('three', { paths: [nestedIndex] })
-  }, /^Error: Cannot find module 'three'$/);
+  }, /^Error: Cannot find module 'three'/);
 
   // Resolution from nested index directory also checks node_modules.
   assert.strictEqual(
diff --git a/test/parallel/test-internal-modules.js b/test/parallel/test-internal-modules.js
index c61d957acd0542..e6bd0c9e141328 100644
--- a/test/parallel/test-internal-modules.js
+++ b/test/parallel/test-internal-modules.js
@@ -5,7 +5,7 @@ const assert = require('assert');
 
 assert.throws(function() {
   require('internal/freelist');
-}, /^Error: Cannot find module 'internal\/freelist'$/);
+}, /^Error: Cannot find module 'internal\/freelist'/);
 
 assert.strictEqual(
   require(fixtures.path('internal-modules')),
diff --git a/test/parallel/test-loaders-hidden-from-users.js b/test/parallel/test-loaders-hidden-from-users.js
index 0d752f5718b729..104681bd792bdf 100644
--- a/test/parallel/test-loaders-hidden-from-users.js
+++ b/test/parallel/test-loaders-hidden-from-users.js
@@ -9,7 +9,7 @@ common.expectsError(
     require('internal/bootstrap/loaders');
   }, {
     code: 'MODULE_NOT_FOUND',
-    message: 'Cannot find module \'internal/bootstrap/loaders\''
+    message: /Cannot find module 'internal\/bootstrap\/loaders'/
   }
 );
 
@@ -20,6 +20,6 @@ common.expectsError(
     require('owo');
   }, {
     code: 'MODULE_NOT_FOUND',
-    message: 'Cannot find module \'owo\''
+    message: /Cannot find module 'owo'/
   }
 );
diff --git a/test/parallel/test-module-loading-error.js b/test/parallel/test-module-loading-error.js
index 67dee6a3ba1d4f..40b6de72a3299b 100644
--- a/test/parallel/test-module-loading-error.js
+++ b/test/parallel/test-module-loading-error.js
@@ -80,9 +80,10 @@ common.expectsError(
     message: 'The argument \'id\' must be a non-empty string. Received \'\''
   });
 
-common.expectsError(
+assert.throws(
   () => { require('../fixtures/packages/is-dir'); },
   {
     code: 'MODULE_NOT_FOUND',
-    message: 'Cannot find module \'../fixtures/packages/is-dir\''
-  });
+    message: /Cannot find module '\.\.\/fixtures\/packages\/is-dir'/
+  }
+);
diff --git a/test/parallel/test-module-multi-extensions.js b/test/parallel/test-module-multi-extensions.js
index be17bc5d025508..1257854115a5b5 100644
--- a/test/parallel/test-module-multi-extensions.js
+++ b/test/parallel/test-module-multi-extensions.js
@@ -35,7 +35,7 @@ fs.writeFileSync(dotfileWithExtension, 'console.log(__filename);', 'utf8');
   require(modulePath);
   assert.throws(
     () => require(`${modulePath}.foo`),
-    new Error(`Cannot find module '${modulePath}.foo'`)
+    (err) => err.message.startsWith(`Cannot find module '${modulePath}.foo'`)
   );
   require(`${modulePath}.foo.bar`);
   delete require.cache[file];
@@ -47,7 +47,7 @@ fs.writeFileSync(dotfileWithExtension, 'console.log(__filename);', 'utf8');
   const modulePath = path.join(tmpdir.path, 'test-extensions');
   assert.throws(
     () => require(modulePath),
-    new Error(`Cannot find module '${modulePath}'`)
+    (err) => err.message.startsWith(`Cannot find module '${modulePath}'`)
   );
   delete require.cache[file];
   Module._pathCache = Object.create(null);
@@ -69,7 +69,7 @@ fs.writeFileSync(dotfileWithExtension, 'console.log(__filename);', 'utf8');
   const modulePath = path.join(tmpdir.path, 'test-extensions.foo');
   assert.throws(
     () => require(modulePath),
-    new Error(`Cannot find module '${modulePath}'`)
+    (err) => err.message.startsWith(`Cannot find module '${modulePath}'`)
   );
   delete require.extensions['.foo.bar'];
   Module._pathCache = Object.create(null);
diff --git a/test/parallel/test-repl.js b/test/parallel/test-repl.js
index 14ada1fe601cca..a53f4a2833d439 100644
--- a/test/parallel/test-repl.js
+++ b/test/parallel/test-repl.js
@@ -534,6 +534,8 @@ const errorTests = [
     expect: [
       'Thrown:',
       /^{ Error: Cannot find module 'internal\/repl'/,
+      /^Require stack:/,
+      /^- <repl>/,
       /^    at .*/,
       /^    at .*/,
       /^    at .*/,
diff --git a/test/sequential/test-module-loading.js b/test/sequential/test-module-loading.js
index 6cfa4da04e2c04..90ab1d4f4f285c 100644
--- a/test/sequential/test-module-loading.js
+++ b/test/sequential/test-module-loading.js
@@ -131,7 +131,7 @@ require('../fixtures/node_modules/foo');
   assert.ok(my_path.path_func instanceof Function);
   // this one does not exist and should throw
   assert.throws(function() { require('./utils'); },
-                /^Error: Cannot find module '\.\/utils'$/);
+                /^Error: Cannot find module '\.\/utils'/);
 }
 
 let errorThrown = false;
@@ -170,12 +170,13 @@ assert.strictEqual(require('../fixtures/registerExt2').custom, 'passed');
 assert.strictEqual(require('../fixtures/foo').foo, 'ok');
 
 // Should not attempt to load a directory
-try {
-  tmpdir.refresh();
-  require(tmpdir.path);
-} catch (err) {
-  assert.strictEqual(err.message, `Cannot find module '${tmpdir.path}'`);
-}
+assert.throws(
+  () => {
+    tmpdir.refresh();
+    require(tmpdir.path);
+  },
+  (err) => err.message.startsWith(`Cannot find module '${tmpdir.path}`)
+);
 
 {
   // Check load order is as expected