diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0d13a1c27a04..8618f3a162ff 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -26,6 +26,7 @@
 - `[jest-core]` Fix incorrect `passWithNoTests` warning ([#8595](https://github.com/facebook/jest/pull/8595))
 - `[jest-snapshots]` Fix test retries that contain snapshots ([#8629](https://github.com/facebook/jest/pull/8629))
 - `[jest-mock]` Fix incorrect assignments when restoring mocks in instances where they originally didn't exist ([#8631](https://github.com/facebook/jest/pull/8631))
+- `[jest-resolve]`: Improve error on module not found ([#8704](https://github.com/facebook/jest/pull/8704)
 
 ### Chore & Maintenance
 
diff --git a/e2e/__tests__/__snapshots__/moduleNameMapper.test.ts.snap b/e2e/__tests__/__snapshots__/moduleNameMapper.test.ts.snap
index a3759f42c96f..770bef15172e 100644
--- a/e2e/__tests__/__snapshots__/moduleNameMapper.test.ts.snap
+++ b/e2e/__tests__/__snapshots__/moduleNameMapper.test.ts.snap
@@ -32,4 +32,5 @@ FAIL __tests__/index.js
 
       at createNoMappedModuleFoundError (../../packages/jest-resolve/build/index.js:501:17)
       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..2c1802570af1
--- /dev/null
+++ b/e2e/__tests__/__snapshots__/requireMissingExt.test.ts.snap
@@ -0,0 +1,27 @@
+// Jest Snapshot v1, https://goo.gl/fbAQLP
+
+exports[`shows a proper error from deep requires 1`] = `
+FAIL ./test.js
+  ● Test suite failed to run
+
+    Cannot find module '../package' from 'node_modules/discord.js/src/index.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/en/configuration#modulefileextensions-array-string
+
+       8 | 'use strict';
+       9 |
+    > 10 | require('discord.js');
+         | ^
+      11 |
+      12 | test('dummy', () => {
+      13 |   expect(1).toBe(1);
+
+      at Resolver.resolveModule (../../packages/jest-resolve/build/index.js:259:17)
+      at Object.<anonymous> (node_modules/discord.js/src/index.js:21:12)
+      at Object.require (test.js:10:1)
+`;
diff --git a/e2e/__tests__/__snapshots__/resolveNoFileExtensions.test.ts.snap b/e2e/__tests__/__snapshots__/resolveNoFileExtensions.test.ts.snap
index 7a66f6098b01..64b8afe59385 100644
--- a/e2e/__tests__/__snapshots__/resolveNoFileExtensions.test.ts.snap
+++ b/e2e/__tests__/__snapshots__/resolveNoFileExtensions.test.ts.snap
@@ -35,4 +35,5 @@ FAIL __tests__/test.js
 
       at Resolver.resolveModule (../../packages/jest-resolve/build/index.js:259:17)
       at Object.require (index.js:3:18)
+      at Object.require (__tests__/test.js:3:11)
 `;
diff --git a/e2e/__tests__/requireMissingExt.test.ts b/e2e/__tests__/requireMissingExt.test.ts
new file mode 100644
index 000000000000..a3eb2c264767
--- /dev/null
+++ b/e2e/__tests__/requireMissingExt.test.ts
@@ -0,0 +1,24 @@
+/**
+ * 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 path from 'path';
+import wrap from 'jest-snapshot-serializer-raw';
+import {extractSummary, run} from '../Utils';
+import runJest from '../runJest';
+
+const dir = path.resolve(__dirname, '../require-missing-ext');
+
+beforeEach(() => {
+  run('yarn', dir);
+});
+
+test('shows a proper error from deep requires', () => {
+  const {stderr} = runJest(dir);
+  const {rest} = extractSummary(stderr);
+
+  expect(wrap(rest)).toMatchSnapshot();
+});
diff --git a/e2e/__tests__/stackTrace.test.ts b/e2e/__tests__/stackTrace.test.ts
index a65a73883748..a9a6b1ef275e 100644
--- a/e2e/__tests__/stackTrace.test.ts
+++ b/e2e/__tests__/stackTrace.test.ts
@@ -78,7 +78,7 @@ describe('Stack Trace', () => {
 
     // Make sure we show Jest's jest-resolve as part of the stack trace
     expect(stderr).toMatch(
-      /Cannot find module 'this-module-does-not-exist' from 'testError.test\.js'/,
+      /Cannot find module 'this-module-does-not-exist' from '__tests__\/testError\.test\.js'/,
     );
 
     expect(stderr).toMatch(
diff --git a/e2e/require-missing-ext/package.json b/e2e/require-missing-ext/package.json
new file mode 100644
index 000000000000..9a156e8c5f0a
--- /dev/null
+++ b/e2e/require-missing-ext/package.json
@@ -0,0 +1,11 @@
+{
+  "jest": {
+    "moduleFileExtensions": [
+      "js"
+    ],
+    "testEnvironment": "node"
+  },
+  "dependencies": {
+    "discord.js": "11.5.1"
+  }
+}
diff --git a/e2e/require-missing-ext/test.js b/e2e/require-missing-ext/test.js
new file mode 100644
index 000000000000..55370ccafe8f
--- /dev/null
+++ b/e2e/require-missing-ext/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/yarn.lock b/e2e/require-missing-ext/yarn.lock
new file mode 100644
index 000000000000..6db023090213
--- /dev/null
+++ b/e2e/require-missing-ext/yarn.lock
@@ -0,0 +1,46 @@
+# THIS IS AN AUTOGENERATED FILE. DO NOT EDIT THIS FILE DIRECTLY.
+# yarn lockfile v1
+
+
+async-limiter@~1.0.0:
+  version "1.0.0"
+  resolved "https://registry.yarnpkg.com/async-limiter/-/async-limiter-1.0.0.tgz#78faed8c3d074ab81f22b4e985d79e8738f720f8"
+  integrity sha512-jp/uFnooOiO+L211eZOoSyzpOITMXx1rBITauYykG3BRYPu8h0UcxsPNB04RR5vo4Tyz3+ay17tR6JVf9qzYWg==
+
+discord.js@11.5.1:
+  version "11.5.1"
+  resolved "https://registry.yarnpkg.com/discord.js/-/discord.js-11.5.1.tgz#910fb9f6410328581093e044cafb661783a4d9e8"
+  integrity sha512-tGhV5xaZXE3Z+4uXJb3hYM6gQ1NmnSxp9PClcsSAYFVRzH6AJH74040mO3afPDMWEAlj8XsoPXXTJHTxesqcGw==
+  dependencies:
+    long "^4.0.0"
+    prism-media "^0.0.3"
+    snekfetch "^3.6.4"
+    tweetnacl "^1.0.0"
+    ws "^6.0.0"
+
+long@^4.0.0:
+  version "4.0.0"
+  resolved "https://registry.yarnpkg.com/long/-/long-4.0.0.tgz#9a7b71cfb7d361a194ea555241c92f7468d5bf28"
+  integrity sha512-XsP+KhQif4bjX1kbuSiySJFNAehNxgLb6hPRGJ9QsUr8ajHkuXGdrHmFUTUUXhDwVX2R5bY4JNZEwbUiMhV+MA==
+
+prism-media@^0.0.3:
+  version "0.0.3"
+  resolved "https://registry.yarnpkg.com/prism-media/-/prism-media-0.0.3.tgz#8842d4fae804f099d3b48a9a38e3c2bab6f4855b"
+  integrity sha512-c9KkNifSMU/iXT8FFTaBwBMr+rdVcN+H/uNv1o+CuFeTThNZNTOrQ+RgXA1yL/DeLk098duAeRPP3QNPNbhxYQ==
+
+snekfetch@^3.6.4:
+  version "3.6.4"
+  resolved "https://registry.yarnpkg.com/snekfetch/-/snekfetch-3.6.4.tgz#d13e80a616d892f3d38daae4289f4d258a645120"
+  integrity sha512-NjxjITIj04Ffqid5lqr7XdgwM7X61c/Dns073Ly170bPQHLm6jkmelye/eglS++1nfTWktpP6Y2bFXjdPlQqdw==
+
+tweetnacl@^1.0.0:
+  version "1.0.1"
+  resolved "https://registry.yarnpkg.com/tweetnacl/-/tweetnacl-1.0.1.tgz#2594d42da73cd036bd0d2a54683dd35a6b55ca17"
+  integrity sha512-kcoMoKTPYnoeS50tzoqjPY3Uv9axeuuFAZY9M/9zFnhoVvRfxz9K29IMPD7jGmt2c8SW7i3gT9WqDl2+nV7p4A==
+
+ws@^6.0.0:
+  version "6.2.1"
+  resolved "https://registry.yarnpkg.com/ws/-/ws-6.2.1.tgz#442fdf0a47ed64f59b6a5d8ff130f4748ed524fb"
+  integrity sha512-GIyAXC2cB7LjvpgMt9EKS2ldqr0MTrORaleiOno6TweZ6r3TKtoFQWay/2PceJ3RuBasOHzXNn5Lrw1X0bEjqA==
+  dependencies:
+    async-limiter "~1.0.0"
diff --git a/packages/jest-environment-node/src/index.ts b/packages/jest-environment-node/src/index.ts
index bc82af123b5e..4b469839ea47 100644
--- a/packages/jest-environment-node/src/index.ts
+++ b/packages/jest-environment-node/src/index.ts
@@ -52,6 +52,9 @@ class NodeEnvironment implements JestEnvironment {
       global.TextDecoder = TextDecoder;
     }
     installCommonGlobals(global, config.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;
     this.moduleMocker = new ModuleMocker(global);
 
     const timerIdToRef = (id: number) => ({
diff --git a/packages/jest-resolve/src/index.ts b/packages/jest-resolve/src/index.ts
index 9e21e5faa806..fedfe7362f72 100644
--- a/packages/jest-resolve/src/index.ts
+++ b/packages/jest-resolve/src/index.ts
@@ -208,9 +208,9 @@ class Resolver {
     // 5. Throw an error if the module could not be found. `resolve.sync` only
     // produces an error based on the dirname but we have the actual current
     // module name available.
-    const relativePath = path.relative(dirname, from);
+    const relativePath = path.relative(this._options.rootDir, from) || '.';
     const err: Error & {code?: string} = new Error(
-      `Cannot find module '${moduleName}' from '${relativePath || '.'}'`,
+      `Cannot find module '${moduleName}' from '${relativePath}'`,
     );
     err.code = 'MODULE_NOT_FOUND';
     throw err;
diff --git a/packages/jest-runner/src/runTest.ts b/packages/jest-runner/src/runTest.ts
index 860105dc99e1..7589813c9c37 100644
--- a/packages/jest-runner/src/runTest.ts
+++ b/packages/jest-runner/src/runTest.ts
@@ -84,6 +84,9 @@ async function runTestInternal(
   resolver: Resolver,
   context?: TestRunnerContext,
 ): Promise<RunTestInternalResult> {
+  // 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;
   const testSource = fs.readFileSync(path, 'utf8');
   const docblockPragmas = docblock.parse(docblock.extract(testSource));
   const customEnvironment = docblockPragmas['jest-environment'];