diff --git a/CHANGELOG.md b/CHANGELOG.md
index 809ddbc317df..d2de38038ddf 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,7 +10,8 @@
 ### Fixes
 
 - `[jest-core]` Capture execError during `TestScheduler.scheduleTests` and dispatch to reporters ([#13203](https://github.com/facebook/jest/pull/13203))
-- `[jest-resolver]` Make sure to resolve module paths after looking at `exports` ([#13242](https://github.com/facebook/jest/pull/13242))
+- `[jest-resolve]` Make sure to resolve module paths after looking at `exports` ([#13242](https://github.com/facebook/jest/pull/13242))
+- `[jest-resolve]` Improve error on module not found deep in the `require` stack ([#8704](https://github.com/facebook/jest/pull/8704)
 - `[jest-snapshot]` Fix typings of snapshot matchers ([#13240])(https://github.com/facebook/jest/pull/13240))
 
 ### Chore & Maintenance
diff --git a/e2e/__tests__/__snapshots__/moduleNameMapper.test.ts.snap b/e2e/__tests__/__snapshots__/moduleNameMapper.test.ts.snap
index 62553cf7f7aa..c7eb02d6cfe1 100644
--- a/e2e/__tests__/__snapshots__/moduleNameMapper.test.ts.snap
+++ b/e2e/__tests__/__snapshots__/moduleNameMapper.test.ts.snap
@@ -42,7 +42,8 @@ exports[`moduleNameMapper wrong array configuration 1`] = `
       13 |
 
       at createNoMappedModuleFoundError (../../packages/jest-resolve/build/resolver.js:896:17)
-      at Object.require (index.js:10:1)"
+      at Object.require (index.js:10:1)
+      at Object.require (__tests__/index.js:10:20)"
 `;
 
 exports[`moduleNameMapper wrong configuration 1`] = `
@@ -71,5 +72,6 @@ exports[`moduleNameMapper wrong configuration 1`] = `
       13 |
 
       at createNoMappedModuleFoundError (../../packages/jest-resolve/build/resolver.js:896:17)
-      at Object.require (index.js:10:1)"
+      at Object.require (index.js:10:1)
+      at Object.require (__tests__/index.js:10:20)"
 `;
diff --git a/e2e/__tests__/__snapshots__/requireMissingExt.test.ts.snap b/e2e/__tests__/__snapshots__/requireMissingExt.test.ts.snap
new file mode 100644
index 000000000000..b3a529188daa
--- /dev/null
+++ b/e2e/__tests__/__snapshots__/requireMissingExt.test.ts.snap
@@ -0,0 +1,32 @@
+// Jest Snapshot v1, https://goo.gl/fbAQLP
+
+exports[`shows a proper error from deep requires 1`] = `
+"FAIL __tests__/test.js
+  ● Test suite failed to run
+
+    Cannot find module '../package' from 'node_modules/discord.js/src/index.js'
+
+    Require stack:
+      node_modules/discord.js/src/index.js
+      __tests__/test.js
+
+
+    However, Jest was able to find:
+    	'../package.json'
+
+    You might want to include a file extension in your import, or update your 'moduleFileExtensions', which is currently ['js'].
+
+    See https://jestjs.io/docs/configuration#modulefileextensions-arraystring
+
+       8 | 'use strict';
+       9 |
+    > 10 | require('discord.js');
+         | ^
+      11 |
+      12 | test('dummy', () => {
+      13 |   expect(1).toBe(1);
+
+      at Resolver._throwModNotFoundError (../../packages/jest-resolve/build/resolver.js:487:11)
+      at Object.<anonymous> (node_modules/discord.js/src/index.js:21:12)
+      at Object.require (__tests__/test.js:10:1)"
+`;
diff --git a/e2e/__tests__/__snapshots__/resolveNoFileExtensions.test.ts.snap b/e2e/__tests__/__snapshots__/resolveNoFileExtensions.test.ts.snap
index 62ed2a7e4489..b906b0cf9d7d 100644
--- a/e2e/__tests__/__snapshots__/resolveNoFileExtensions.test.ts.snap
+++ b/e2e/__tests__/__snapshots__/resolveNoFileExtensions.test.ts.snap
@@ -38,5 +38,6 @@ exports[`show error message with matching files 1`] = `
       9 |
 
       at Resolver._throwModNotFoundError (../../packages/jest-resolve/build/resolver.js:487:11)
-      at Object.require (index.js:8:18)"
+      at Object.require (index.js:8:18)
+      at Object.require (__tests__/test.js:8:11)"
 `;
diff --git a/e2e/__tests__/requireMissingExt.test.ts b/e2e/__tests__/requireMissingExt.test.ts
new file mode 100644
index 000000000000..3421e13af9da
--- /dev/null
+++ b/e2e/__tests__/requireMissingExt.test.ts
@@ -0,0 +1,23 @@
+/**
+ * Copyright (c) Facebook, Inc. and its affiliates. All Rights Reserved.
+ *
+ * This source code is licensed under the MIT license found in the
+ * LICENSE file in the root directory of this source tree.
+ */
+
+import * as path from 'path';
+import {extractSummary, runYarnInstall} from '../Utils';
+import runJest from '../runJest';
+
+const dir = path.resolve(__dirname, '../require-missing-ext');
+
+beforeEach(() => {
+  runYarnInstall(dir);
+});
+
+test('shows a proper error from deep requires', () => {
+  const {stderr} = runJest(dir);
+  const {rest} = extractSummary(stderr);
+
+  expect(rest).toMatchSnapshot();
+});
diff --git a/e2e/require-missing-ext/__tests__/test.js b/e2e/require-missing-ext/__tests__/test.js
new file mode 100644
index 000000000000..55370ccafe8f
--- /dev/null
+++ b/e2e/require-missing-ext/__tests__/test.js
@@ -0,0 +1,14 @@
+/**
+ * Copyright (c) Facebook, Inc. and its affiliates. All Rights Reserved.
+ *
+ * This source code is licensed under the MIT license found in the
+ * LICENSE file in the root directory of this source tree.
+ */
+
+'use strict';
+
+require('discord.js');
+
+test('dummy', () => {
+  expect(1).toBe(1);
+});
diff --git a/e2e/require-missing-ext/package.json b/e2e/require-missing-ext/package.json
new file mode 100644
index 000000000000..b560faa1f460
--- /dev/null
+++ b/e2e/require-missing-ext/package.json
@@ -0,0 +1,10 @@
+{
+  "jest": {
+    "moduleFileExtensions": [
+      "js"
+    ]
+  },
+  "dependencies": {
+    "discord.js": "11.5.1"
+  }
+}
diff --git a/e2e/require-missing-ext/yarn.lock b/e2e/require-missing-ext/yarn.lock
new file mode 100644
index 000000000000..bc174f12123f
--- /dev/null
+++ b/e2e/require-missing-ext/yarn.lock
@@ -0,0 +1,94 @@
+# This file is generated by running "yarn install" inside your project.
+# Manual changes might be lost - proceed with caution!
+
+__metadata:
+  version: 6
+  cacheKey: 8
+
+"async-limiter@npm:~1.0.0":
+  version: 1.0.1
+  resolution: "async-limiter@npm:1.0.1"
+  checksum: 2b849695b465d93ad44c116220dee29a5aeb63adac16c1088983c339b0de57d76e82533e8e364a93a9f997f28bbfc6a92948cefc120652bd07f3b59f8d75cf2b
+  languageName: node
+  linkType: hard
+
+"discord.js@npm:11.5.1":
+  version: 11.5.1
+  resolution: "discord.js@npm:11.5.1"
+  dependencies:
+    long: ^4.0.0
+    prism-media: ^0.0.3
+    snekfetch: ^3.6.4
+    tweetnacl: ^1.0.0
+    ws: ^6.0.0
+  peerDependencies:
+    "@discordjs/uws": ^10.149.0
+    bufferutil: ^4.0.0
+    erlpack: "*"
+    libsodium-wrappers: ^0.7.3
+    node-opus: ^0.2.7
+    opusscript: ^0.0.6
+    sodium: ^2.0.3
+  peerDependenciesMeta:
+    bufferutil:
+      optional: true
+    erlpack:
+      optional: true
+    libsodium-wrappers:
+      optional: true
+    node-opus:
+      optional: true
+    opusscript:
+      optional: true
+    sodium:
+      optional: true
+    uws:
+      optional: true
+  checksum: fdd210b1a63bff6d39eae8c79beb2f1035d16b029a361142f9148e3ba6819e685872af2435e8cfef0b71b4871f14d4bcb7a4ce9f4c957c7a4aca1a347b3229f0
+  languageName: node
+  linkType: hard
+
+"long@npm:^4.0.0":
+  version: 4.0.0
+  resolution: "long@npm:4.0.0"
+  checksum: 16afbe8f749c7c849db1f4de4e2e6a31ac6e617cead3bdc4f9605cb703cd20e1e9fc1a7baba674ffcca57d660a6e5b53a9e236d7b25a295d3855cca79cc06744
+  languageName: node
+  linkType: hard
+
+"prism-media@npm:^0.0.3":
+  version: 0.0.3
+  resolution: "prism-media@npm:0.0.3"
+  checksum: 45d56138bd48616d78ec2f09b77e3700c88a4e08fb159949ee0b47fe5ce9db2d68ceac4729faebada4a23b640a9f984e7dd9b4bc72b2f52666307ca9d559fcfb
+  languageName: node
+  linkType: hard
+
+"root-workspace-0b6124@workspace:.":
+  version: 0.0.0-use.local
+  resolution: "root-workspace-0b6124@workspace:."
+  dependencies:
+    discord.js: 11.5.1
+  languageName: unknown
+  linkType: soft
+
+"snekfetch@npm:^3.6.4":
+  version: 3.6.4
+  resolution: "snekfetch@npm:3.6.4"
+  checksum: e64b383a19ced759f061ecd43bc9a75bcc9b996d1909f9b94e6aaf66b6579024340c904af05aeba6261a8dd4ad9f71763f47e134c8089707d4be10fcfc682ed9
+  languageName: node
+  linkType: hard
+
+"tweetnacl@npm:^1.0.0":
+  version: 1.0.3
+  resolution: "tweetnacl@npm:1.0.3"
+  checksum: e4a57cac188f0c53f24c7a33279e223618a2bfb5fea426231991652a13247bea06b081fd745d71291fcae0f4428d29beba1b984b1f1ce6f66b06a6d1ab90645c
+  languageName: node
+  linkType: hard
+
+"ws@npm:^6.0.0":
+  version: 6.2.2
+  resolution: "ws@npm:6.2.2"
+  dependencies:
+    async-limiter: ~1.0.0
+  checksum: aec3154ec51477c094ac2cb5946a156e17561a581fa27005cbf22c53ac57f8d4e5f791dd4bbba6a488602cb28778c8ab7df06251d590507c3c550fd8ebeee949
+  languageName: node
+  linkType: hard
diff --git a/packages/jest-environment-node/src/index.ts b/packages/jest-environment-node/src/index.ts
index 96c5db2acffa..97f8e319f7ba 100644
--- a/packages/jest-environment-node/src/index.ts
+++ b/packages/jest-environment-node/src/index.ts
@@ -112,6 +112,10 @@ export default class NodeEnvironment implements JestEnvironment<Timer> {
 
     installCommonGlobals(global, projectConfig.globals);
 
+    // Node's error-message stack size is limited at 10, but it's pretty useful
+    // to see more than that when a test fails.
+    global.Error.stackTraceLimit = 100;
+
     if ('customExportConditions' in projectConfig.testEnvironmentOptions) {
       const {customExportConditions} = projectConfig.testEnvironmentOptions;
       if (
diff --git a/packages/jest-runner/src/runTest.ts b/packages/jest-runner/src/runTest.ts
index f743d3b76f6d..40b69f771207 100644
--- a/packages/jest-runner/src/runTest.ts
+++ b/packages/jest-runner/src/runTest.ts
@@ -273,6 +273,9 @@ async function runTestInternal(
     globalConfig.coverageProvider === 'v8' &&
     typeof environment.getVmContext === 'function';
 
+  // Node's error-message stack size is limited at 10, but it's pretty useful
+  // to see more than that when a test fails.
+  Error.stackTraceLimit = 100;
   try {
     await environment.setup();