diff --git a/packages/playwright/src/matchers/expect.ts b/packages/playwright/src/matchers/expect.ts
index a0d5dff91e..18d5c6b597 100644
--- a/packages/playwright/src/matchers/expect.ts
+++ b/packages/playwright/src/matchers/expect.ts
@@ -48,7 +48,7 @@ import {
 import { toMatchSnapshot, toHaveScreenshot, toHaveScreenshotStepTitle } from './toMatchSnapshot';
 import type { Expect } from '../../types/test';
 import { currentTestInfo, currentExpectTimeout, setCurrentExpectConfigureTimeout } from '../common/globals';
-import { filteredStackTrace, serializeError, stringifyStackFrames, trimLongString } from '../util';
+import { filteredStackTrace, stringifyStackFrames, trimLongString } from '../util';
 import {
   expect as expectLibrary,
   INVERTED_COLOR,
@@ -106,7 +106,7 @@ function createMatchers(actual: unknown, info: ExpectMetaInfo): any {
 }
 
 function createExpect(info: ExpectMetaInfo) {
-  const expectInstance: Expect = new Proxy(expectLibrary, {
+  const expectInstance: Expect<{}> = new Proxy(expectLibrary, {
     apply: function(target: any, thisArg: any, argumentsList: [unknown, ExpectMessage?]) {
       const [actual, messageOrOptions] = argumentsList;
       const message = isString(messageOrOptions) ? messageOrOptions : messageOrOptions?.message || info.message;
@@ -123,6 +123,13 @@ function createExpect(info: ExpectMetaInfo) {
       if (property === 'configure')
         return configure;
 
+      if (property === 'extend') {
+        return (matchers: any) => {
+          expectLibrary.extend(matchers);
+          return expectInstance;
+        };
+      }
+
       if (property === 'soft') {
         return (actual: unknown, messageOrOptions?: ExpectMessage) => {
           return configure({ soft: true })(actual, messageOrOptions) as any;
@@ -160,7 +167,7 @@ function createExpect(info: ExpectMetaInfo) {
   return expectInstance;
 }
 
-export const expect: Expect = createExpect({});
+export const expect: Expect<{}> = createExpect({});
 
 expectLibrary.setState({ expand: false });
 
@@ -269,9 +276,13 @@ class ExpectMetaInfoProxyHandler implements ProxyHandler<any> {
           jestError.stack = jestError.name + ': ' + newMessage + '\n' + stringifyStackFrames(stackFrames).join('\n');
         }
 
-        const serializedError = serializeError(jestError);
-        // Serialized error has filtered stack trace.
-        jestError.stack = serializedError.stack;
+        // Use the exact stack that we entered the matcher with.
+        jestError.stack = jestError.name + ': ' + jestError.message + '\n' + stringifyStackFrames(stackFrames).join('\n');
+        const serializedError = {
+          message: jestError.message,
+          stack: jestError.stack,
+        };
+
         step?.complete({ error: serializedError });
         if (this._info.isSoft)
           testInfo._failWithError(serializedError, false /* isHardError */);
diff --git a/packages/playwright/src/matchers/toBeTruthy.ts b/packages/playwright/src/matchers/toBeTruthy.ts
index 751d4e4756..c7f5a4906e 100644
--- a/packages/playwright/src/matchers/toBeTruthy.ts
+++ b/packages/playwright/src/matchers/toBeTruthy.ts
@@ -48,5 +48,5 @@ export async function toBeTruthy(
     return matches ? `${header}Expected: not ${expected}\nReceived: ${expected}${logText}` :
       `${header}Expected: ${expected}\nReceived: ${unexpected}${logText}`;
   };
-  return { locator: receiver, message, pass: matches, actual, name: matcherName, expected, log };
+  return { message, pass: matches, actual, name: matcherName, expected, log };
 }
diff --git a/packages/playwright/src/matchers/toEqual.ts b/packages/playwright/src/matchers/toEqual.ts
index 4c47700e0a..a4bf47030c 100644
--- a/packages/playwright/src/matchers/toEqual.ts
+++ b/packages/playwright/src/matchers/toEqual.ts
@@ -67,5 +67,5 @@ export async function toEqual<T>(
   // Passing the actual and expected objects so that a custom reporter
   // could access them, for example in order to display a custom visual diff,
   // or create a different error message
-  return { locator: receiver, actual: received, expected, message, name: matcherName, pass, log };
+  return { actual: received, expected, message, name: matcherName, pass, log };
 }
diff --git a/packages/playwright/src/matchers/toMatchText.ts b/packages/playwright/src/matchers/toMatchText.ts
index efeb5280b8..3a5f39b0d9 100644
--- a/packages/playwright/src/matchers/toMatchText.ts
+++ b/packages/playwright/src/matchers/toMatchText.ts
@@ -99,7 +99,6 @@ export async function toMatchText(
     };
 
   return {
-    locator: receiver,
     name: matcherName,
     expected,
     message,
diff --git a/packages/playwright/types/test.d.ts b/packages/playwright/types/test.d.ts
index abbf6f03ab..cb6be198c8 100644
--- a/packages/playwright/types/test.d.ts
+++ b/packages/playwright/types/test.d.ts
@@ -3363,7 +3363,7 @@ export interface TestType<TestArgs extends KeyValue, WorkerArgs extends KeyValue
    * ```
    *
    */
-  expect: Expect;
+  expect: Expect<{}>;
   /**
    * Extends the `test` object by defining fixtures and/or options that can be used in the tests.
    *
@@ -5083,38 +5083,81 @@ type AllMatchers<R, T> = PageAssertions & LocatorAssertions & APIResponseAsserti
 
 type IfAny<T, Y, N> = 0 extends (1 & T) ? Y : N;
 type Awaited<T> = T extends PromiseLike<infer U> ? U : T;
-type MakeMatchers<R, T> = {
+type ToUserMatcher<F> = F extends (first: any, ...args: infer Rest) => infer R ? (...args: Rest) => (R extends PromiseLike<infer U> ? Promise<void> : void) : never;
+type ToUserMatcherObject<T, ArgType> = {
+  [K in keyof T as T[K] extends (arg: ArgType, ...rest: any[]) => any ? K : never]: ToUserMatcher<T[K]>;
+};
+
+type MatcherHintColor = (arg: string) => string;
+
+export type MatcherHintOptions = {
+  comment?: string;
+  expectedColor?: MatcherHintColor;
+  isDirectExpectCall?: boolean;
+  isNot?: boolean;
+  promise?: string;
+  receivedColor?: MatcherHintColor;
+  secondArgument?: string;
+  secondArgumentColor?: MatcherHintColor;
+};
+
+export interface ExpectMatcherUtils {
+  matcherHint(matcherName: string, received: unknown, expected: unknown, options?: MatcherHintOptions): string;
+  printDiffOrStringify(expected: unknown, received: unknown, expectedLabel: string, receivedLabel: string, expand: boolean): string;
+  printExpected(value: unknown): string;
+  printReceived(object: unknown): string;
+  printWithType<T>(name: string, value: T, print: (value: T) => string): string;
+  diff(a: unknown, b: unknown): string | null;
+  stringify(object: unknown, maxDepth?: number, maxWidth?: number): string;
+}
+
+type State = {
+  isNot: boolean;
+  promise: 'rejects' | 'resolves' | '';
+  utils: ExpectMatcherUtils;
+};
+
+type MatcherReturnType = {
+  message: () => string;
+  pass: boolean;
+  name?: string;
+  expected?: unknown;
+  actual?: any;
+  log?: string[];
+};
+
+type MakeMatchers<R, T, ExtendedMatchers> = {
   /**
    * If you know how to test something, `.not` lets you test its opposite.
    */
-  not: MakeMatchers<R, T>;
+  not: MakeMatchers<R, T, ExtendedMatchers>;
   /**
    * Use resolves to unwrap the value of a fulfilled promise so any other
    * matcher can be chained. If the promise is rejected the assertion fails.
    */
-  resolves: MakeMatchers<Promise<R>, Awaited<T>>;
+  resolves: MakeMatchers<Promise<R>, Awaited<T>, ExtendedMatchers>;
   /**
    * Unwraps the reason of a rejected promise so any other matcher can be chained.
    * If the promise is fulfilled the assertion fails.
    */
-  rejects: MakeMatchers<Promise<R>, any>;
-} & IfAny<T, AllMatchers<R, T>, SpecificMatchers<R, T>>;
+  rejects: MakeMatchers<Promise<R>, any, ExtendedMatchers>;
+} & IfAny<T, AllMatchers<R, T>, SpecificMatchers<R, T> & ToUserMatcherObject<ExtendedMatchers, T>>;
 
-export type Expect = {
-  <T = unknown>(actual: T, messageOrOptions?: string | { message?: string }): MakeMatchers<void, T>;
-  soft: <T = unknown>(actual: T, messageOrOptions?: string | { message?: string }) => MakeMatchers<void, T>;
+export type Expect<ExtendedMatchers> = {
+  <T = unknown>(actual: T, messageOrOptions?: string | { message?: string }): MakeMatchers<void, T, ExtendedMatchers>;
+  soft: <T = unknown>(actual: T, messageOrOptions?: string | { message?: string }) => MakeMatchers<void, T, ExtendedMatchers>;
   poll: <T = unknown>(actual: () => T | Promise<T>, messageOrOptions?: string | { message?: string, timeout?: number, intervals?: number[] }) => BaseMatchers<Promise<void>, T> & {
     /**
      * If you know how to test something, `.not` lets you test its opposite.
      */
      not: BaseMatchers<Promise<void>, T>;
   };
-  extend(matchers: any): void;
+  extend<MoreMatchers extends Record<string, (this: State, receiver: any, ...args: any[]) => MatcherReturnType | Promise<MatcherReturnType>>>(matchers: MoreMatchers): Expect<ExtendedMatchers & MoreMatchers>;
   configure: (configuration: {
     message?: string,
     timeout?: number,
     soft?: boolean,
-  }) => Expect;
+  }) => Expect<ExtendedMatchers>;
   getState(): {
     expand?: boolean;
     isNot?: boolean;
@@ -5141,7 +5184,7 @@ export const test: TestType<PlaywrightTestArgs & PlaywrightTestOptions, Playwrig
 export default test;
 
 export const _baseTest: TestType<{}, {}>;
-export const expect: Expect;
+export const expect: Expect<{}>;
 
 /**
  * Defines Playwright config
diff --git a/tests/installation/expect.d.ts b/tests/installation/expect.d.ts
deleted file mode 100644
index e8ccb161f7..0000000000
--- a/tests/installation/expect.d.ts
+++ /dev/null
@@ -1,25 +0,0 @@
-/**
- * Copyright (c) Microsoft Corporation.
- *
- * Licensed under the Apache License, Version 2.0 (the "License");
- * you may not use this file except in compliance with the License.
- * You may obtain a copy of the License at
- *
- * http://www.apache.org/licenses/LICENSE-2.0
- *
- * Unless required by applicable law or agreed to in writing, software
- * distributed under the License is distributed on an "AS IS" BASIS,
- * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
- * See the License for the specific language governing permissions and
- * limitations under the License.
- */
-
-export {}
-
-declare global {
-    namespace PlaywrightTest {
-       interface Matchers<R, T> {
-          toHaveLoggedSoftwareDownload(browsers: ("chromium" | "firefox" | "webkit" | "ffmpeg")[]): R;
-       }
-    }
-}
diff --git a/tests/installation/npmTest.ts b/tests/installation/npmTest.ts
index 5c8bd27870..987f75477e 100644
--- a/tests/installation/npmTest.ts
+++ b/tests/installation/npmTest.ts
@@ -14,9 +14,6 @@
  * limitations under the License.
  */
 
-// eslint-disable-next-line spaced-comment
-/// <reference path="./expect.d.ts" />
-
 import { _baseTest as _test, expect as _expect } from '@playwright/test';
 import fs from 'fs';
 import os from 'os';
@@ -32,7 +29,7 @@ export const TMP_WORKSPACES = path.join(os.platform() === 'darwin' ? '/tmp' : os
 
 const debug = debugLogger('itest');
 
-_expect.extend({
+const expect = _expect.extend({
   toHaveLoggedSoftwareDownload(received: any, browsers: ('chromium' | 'firefox' | 'webkit' | 'ffmpeg')[]) {
     if (typeof received !== 'string')
       throw new Error(`Expected argument to be a string.`);
@@ -42,8 +39,12 @@ _expect.extend({
       downloaded.add(browser.toLowerCase());
 
     const expected = browsers;
-    if (expected.length === downloaded.size && expected.every(browser => downloaded.has(browser)))
-      return { pass: true };
+    if (expected.length === downloaded.size && expected.every(browser => downloaded.has(browser))) {
+      return {
+        pass: true,
+        message: () => 'Expected not to download browsers, but did.'
+      };
+    }
     return {
       pass: false,
       message: () => [
@@ -55,8 +56,6 @@ _expect.extend({
   }
 });
 
-const expect = _expect;
-
 type ExecOptions = { cwd?: string, env?: Record<string, string>, message?: string, expectToExitWithError?: boolean };
 type ArgsOrOptions = [] | [...string[]] | [...string[], ExecOptions] | [ExecOptions];
 
@@ -199,7 +198,7 @@ export const test = _test
       },
       tsc: async ({ exec }, use) => {
         await exec('npm i --foreground-scripts typescript@3.8 @types/node@14');
-        await use((...args: ArgsOrOptions) => exec('npx', '-p', 'typescript@3.8', 'tsc', ...args));
+        await use((...args: ArgsOrOptions) => exec('npx', '-p', 'typescript@4.1.6', 'tsc', ...args));
       },
     });
 
diff --git a/tests/page/expect-matcher-result.spec.ts b/tests/page/expect-matcher-result.spec.ts
index 5d7ae66ca7..f5f4f72579 100644
--- a/tests/page/expect-matcher-result.spec.ts
+++ b/tests/page/expect-matcher-result.spec.ts
@@ -25,7 +25,6 @@ test('toMatchText-based assertions should have matcher result', async ({ page })
     const e = await expect(locator).toHaveText(/Text2/, { timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 'Text content',
       expected: /Text2/,
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).toHaveText(expected)`),
@@ -47,7 +46,6 @@ Call log`);
     const e = await expect(locator).not.toHaveText(/Text/, { timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 'Text content',
       expected: /Text/,
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).not.toHaveText(expected)`),
@@ -73,7 +71,6 @@ test('toBeTruthy-based assertions should have matcher result', async ({ page })
     const e = await expect(page.locator('#node2')).toBeVisible({ timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 'hidden',
       expected: 'visible',
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).toBeVisible()`),
@@ -95,7 +92,6 @@ Call log`);
     const e = await expect(page.locator('#node')).not.toBeVisible({ timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 'visible',
       expected: 'visible',
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).not.toBeVisible()`),
@@ -121,7 +117,6 @@ test('toEqual-based assertions should have matcher result', async ({ page }) =>
     const e = await expect(page.locator('#node2')).toHaveCount(1, { timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 0,
       expected: 1,
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).toHaveCount(expected)`),
@@ -142,7 +137,6 @@ Call log`);
     const e = await expect(page.locator('#node')).not.toHaveCount(1, { timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 1,
       expected: 1,
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).not.toHaveCount(expected)`),
@@ -171,7 +165,6 @@ test('toBeChecked({ checked: false }) should have expected: false', async ({ pag
     const e = await expect(page.locator('#unchecked')).toBeChecked({ timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 'unchecked',
       expected: 'checked',
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).toBeChecked()`),
@@ -193,7 +186,6 @@ Call log`);
     const e = await expect(page.locator('#checked')).not.toBeChecked({ timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 'checked',
       expected: 'checked',
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).not.toBeChecked()`),
@@ -215,7 +207,6 @@ Call log`);
     const e = await expect(page.locator('#checked')).toBeChecked({ checked: false, timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 'checked',
       expected: 'unchecked',
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).toBeChecked({ checked: false })`),
@@ -237,7 +228,6 @@ Call log`);
     const e = await expect(page.locator('#unchecked')).not.toBeChecked({ checked: false, timeout: 1 }).catch(e => e);
     e.matcherResult.message = stripAnsi(e.matcherResult.message);
     expect.soft(e.matcherResult).toEqual({
-      locator: expect.any(Object),
       actual: 'unchecked',
       expected: 'unchecked',
       message: expect.stringContaining(`Timed out 1ms waiting for expect(locator).not.toBeChecked({ checked: false })`),
diff --git a/tests/playwright-test/expect.spec.ts b/tests/playwright-test/expect.spec.ts
index d2977dae25..ed20b27e6f 100644
--- a/tests/playwright-test/expect.spec.ts
+++ b/tests/playwright-test/expect.spec.ts
@@ -15,7 +15,7 @@
  */
 
 import path from 'path';
-import { test, expect, parseTestRunnerOutput } from './playwright-test-fixtures';
+import { test, expect, parseTestRunnerOutput, stripAnsi } from './playwright-test-fixtures';
 
 test('should be able to call expect.extend in config', async ({ runInlineTest }) => {
   const result = await runInlineTest({
@@ -273,7 +273,12 @@ test('should work with custom PlaywrightTest namespace', async ({ runTSC }) => {
     'a.spec.ts': `
       import { test, expect, type Page, type APIResponse } from '@playwright/test';
       test.expect.extend({
-        toBeWithinRange() { },
+        toBeWithinRange() {
+          return {
+            pass: true,
+            message: () => '',
+          };
+        },
       });
 
       const page = {} as Page;
@@ -704,3 +709,153 @@ test('should not leak long expect message strings', async ({ runInlineTest }) =>
   expect(result.failed).toBe(0);
   expect(result.exitCode).toBe(0);
 });
+
+test('should chain expect matchers and expose matcher utils (TSC)', async ({ runTSC }) => {
+  const result = await runTSC({
+    'a.spec.ts': `
+    import { test, expect as baseExpect } from '@playwright/test';
+    import type { Page, Locator } from '@playwright/test';
+
+    function callLogText(log: string[] | undefined): string {
+      if (!log)
+        return '';
+      return log.join('\\n');
+    }
+
+    const expect = baseExpect.extend({
+      async toHaveAmount(locator: Locator, expected: string, options?: { timeout?: number }) {
+        const baseAmount = locator.locator('.base-amount');
+
+        let pass: boolean;
+        let matcherResult: any;
+        try {
+          await baseExpect(baseAmount).toHaveAttribute('data-amount', expected, options);
+          pass = true;
+        } catch (e: any) {
+          matcherResult = e.matcherResult;
+          pass = false;
+        }
+
+        const expectOptions = {
+          isNot: this.isNot,
+        };
+
+        const log = callLogText(matcherResult?.log);
+        const message = pass
+          ? () => this.utils.matcherHint('toBe', locator, expected, expectOptions) +
+              '\\n\\n' +
+              \`Expected: \${this.isNot ? 'not' : ''}\${this.utils.printExpected(expected)}\\n\` +
+              (matcherResult ? \`Received: \${this.utils.printReceived(matcherResult.actual)}\` : '') +
+              log
+          : () =>  this.utils.matcherHint('toBe', locator, expected, expectOptions) +
+              '\\n\\n' +
+              \`Expected: \${this.utils.printExpected(expected)}\n\` +
+              (matcherResult ? \`Received: \${this.utils.printReceived(matcherResult.actual)}\` : '') +
+              log;
+
+        return {
+          name: 'toHaveAmount',
+          expected,
+          message,
+          pass,
+          actual: matcherResult?.actual,
+          log: matcherResult?.log,
+        };
+      },
+
+      async toBeANicePage(page: Page) {
+        return {
+          name: 'toBeANicePage',
+          expected: 1,
+          message: () => '',
+          pass: true,
+        };
+      }
+    });
+
+    test('custom matchers', async ({ page }) => {
+      await page.setContent(\`
+        <div>
+          <div class='base-amount' data-amount='2'></div>
+        </div>
+      \`);
+      await expect(page.locator('div')).toHaveAmount('3', { timeout: 1000 });
+      await expect(page).toBeANicePage();
+      // @ts-expect-error
+      await expect(page).toHaveAmount('3', { timeout: 1000 });
+      // @ts-expect-error
+      await expect(page.locator('div')).toBeANicePage();
+    });`
+  });
+  expect(result.exitCode).toBe(0);
+});
+
+test('should chain expect matchers and expose matcher utils', async ({ runInlineTest }) => {
+  const result = await runInlineTest({
+    'a.spec.ts': `
+    import { test, expect as baseExpect } from '@playwright/test';
+    import type { Page, Locator } from '@playwright/test';
+
+    function callLogText(log: string[] | undefined): string {
+      if (!log)
+        return '';
+      return log.join('\\n');
+    }
+
+    const expect = baseExpect.extend({
+      async toHaveAmount(locator: Locator, expected: string, options?: { timeout?: number }) {
+        const baseAmount = locator.locator('.base-amount');
+
+        let pass: boolean;
+        let matcherResult: any;
+        try {
+          await baseExpect(baseAmount).toHaveAttribute('data-amount', expected, options);
+          pass = true;
+        } catch (e: any) {
+          matcherResult = e.matcherResult;
+          pass = false;
+        }
+
+        const expectOptions = {
+          isNot: this.isNot,
+        };
+
+        const log = callLogText(matcherResult?.log);
+        const message = pass
+          ? () => this.utils.matcherHint('toBe', locator, expected, expectOptions) +
+              '\\n\\n' +
+              \`Expected: \${this.isNot ? 'not' : ''}\${this.utils.printExpected(expected)}\\n\` +
+              (matcherResult ? \`Received: \${this.utils.printReceived(matcherResult.actual)}\` : '') +
+              log
+          : () =>  this.utils.matcherHint('toBe', locator, expected, expectOptions) +
+              '\\n\\n' +
+              \`Expected: \${this.utils.printExpected(expected)}\n\` +
+              (matcherResult ? \`Received: \${this.utils.printReceived(matcherResult.actual)}\` : '') +
+              log;
+
+        return {
+          name: 'toHaveAmount',
+          expected,
+          message,
+          pass,
+          actual: matcherResult?.actual,
+          log: matcherResult?.log,
+        };
+      },
+    });
+
+    test('custom matchers', async ({ page }) => {
+      await page.setContent(\`
+        <div>
+          <div class='base-amount' data-amount='2'></div>
+        </div>
+      \`);
+      await expect(page.locator('div')).toHaveAmount('3', { timeout: 1000 });
+    });`
+  }, { workers: 1 });
+  const output = stripAnsi(result.output);
+  expect(output).toContain(`await expect(page.locator('div')).toHaveAmount('3', { timeout: 1000 });`);
+  expect(output).toContain('a.spec.ts:60');
+  expect(result.failed).toBe(1);
+  expect(result.exitCode).toBe(1);
+});
diff --git a/utils/generate_types/index.js b/utils/generate_types/index.js
index c7e15c648c..5d6c19b5b5 100644
--- a/utils/generate_types/index.js
+++ b/utils/generate_types/index.js
@@ -600,6 +600,7 @@ class TypesGenerator {
         'PlaywrightWorkerOptions.defaultBrowserType',
         'PlaywrightWorkerArgs.playwright',
         'Matchers',
+        'ExpectMatcherUtils',
       ]),
       doNotExportClassNames: new Set([...assertionClasses, 'TestProject']),
       includeExperimental,
diff --git a/utils/generate_types/overrides-test.d.ts b/utils/generate_types/overrides-test.d.ts
index 5df0c147de..f95b9b665c 100644
--- a/utils/generate_types/overrides-test.d.ts
+++ b/utils/generate_types/overrides-test.d.ts
@@ -158,7 +158,7 @@ export interface TestType<TestArgs extends KeyValue, WorkerArgs extends KeyValue
   afterAll(title: string, inner: (args: TestArgs & WorkerArgs, testInfo: TestInfo) => Promise<any> | any): void;
   use(fixtures: Fixtures<{}, {}, TestArgs, WorkerArgs>): void;
   step<T>(title: string, body: () => T | Promise<T>): Promise<T>;
-  expect: Expect;
+  expect: Expect<{}>;
   extend<T extends KeyValue, W extends KeyValue = {}>(fixtures: Fixtures<T, W, TestArgs, WorkerArgs>): TestType<TestArgs & T, WorkerArgs & W>;
   info(): TestInfo;
 }
@@ -341,38 +341,81 @@ type AllMatchers<R, T> = PageAssertions & LocatorAssertions & APIResponseAsserti
 
 type IfAny<T, Y, N> = 0 extends (1 & T) ? Y : N;
 type Awaited<T> = T extends PromiseLike<infer U> ? U : T;
-type MakeMatchers<R, T> = {
+type ToUserMatcher<F> = F extends (first: any, ...args: infer Rest) => infer R ? (...args: Rest) => (R extends PromiseLike<infer U> ? Promise<void> : void) : never;
+type ToUserMatcherObject<T, ArgType> = {
+  [K in keyof T as T[K] extends (arg: ArgType, ...rest: any[]) => any ? K : never]: ToUserMatcher<T[K]>;
+};
+
+type MatcherHintColor = (arg: string) => string;
+
+export type MatcherHintOptions = {
+  comment?: string;
+  expectedColor?: MatcherHintColor;
+  isDirectExpectCall?: boolean;
+  isNot?: boolean;
+  promise?: string;
+  receivedColor?: MatcherHintColor;
+  secondArgument?: string;
+  secondArgumentColor?: MatcherHintColor;
+};
+
+export interface ExpectMatcherUtils {
+  matcherHint(matcherName: string, received: unknown, expected: unknown, options?: MatcherHintOptions): string;
+  printDiffOrStringify(expected: unknown, received: unknown, expectedLabel: string, receivedLabel: string, expand: boolean): string;
+  printExpected(value: unknown): string;
+  printReceived(object: unknown): string;
+  printWithType<T>(name: string, value: T, print: (value: T) => string): string;
+  diff(a: unknown, b: unknown): string | null;
+  stringify(object: unknown, maxDepth?: number, maxWidth?: number): string;
+}
+
+type State = {
+  isNot: boolean;
+  promise: 'rejects' | 'resolves' | '';
+  utils: ExpectMatcherUtils;
+};
+
+type MatcherReturnType = {
+  message: () => string;
+  pass: boolean;
+  name?: string;
+  expected?: unknown;
+  actual?: any;
+  log?: string[];
+};
+
+type MakeMatchers<R, T, ExtendedMatchers> = {
   /**
    * If you know how to test something, `.not` lets you test its opposite.
    */
-  not: MakeMatchers<R, T>;
+  not: MakeMatchers<R, T, ExtendedMatchers>;
   /**
    * Use resolves to unwrap the value of a fulfilled promise so any other
    * matcher can be chained. If the promise is rejected the assertion fails.
    */
-  resolves: MakeMatchers<Promise<R>, Awaited<T>>;
+  resolves: MakeMatchers<Promise<R>, Awaited<T>, ExtendedMatchers>;
   /**
    * Unwraps the reason of a rejected promise so any other matcher can be chained.
    * If the promise is fulfilled the assertion fails.
    */
-  rejects: MakeMatchers<Promise<R>, any>;
-} & IfAny<T, AllMatchers<R, T>, SpecificMatchers<R, T>>;
+  rejects: MakeMatchers<Promise<R>, any, ExtendedMatchers>;
+} & IfAny<T, AllMatchers<R, T>, SpecificMatchers<R, T> & ToUserMatcherObject<ExtendedMatchers, T>>;
 
-export type Expect = {
-  <T = unknown>(actual: T, messageOrOptions?: string | { message?: string }): MakeMatchers<void, T>;
-  soft: <T = unknown>(actual: T, messageOrOptions?: string | { message?: string }) => MakeMatchers<void, T>;
+export type Expect<ExtendedMatchers> = {
+  <T = unknown>(actual: T, messageOrOptions?: string | { message?: string }): MakeMatchers<void, T, ExtendedMatchers>;
+  soft: <T = unknown>(actual: T, messageOrOptions?: string | { message?: string }) => MakeMatchers<void, T, ExtendedMatchers>;
   poll: <T = unknown>(actual: () => T | Promise<T>, messageOrOptions?: string | { message?: string, timeout?: number, intervals?: number[] }) => BaseMatchers<Promise<void>, T> & {
     /**
      * If you know how to test something, `.not` lets you test its opposite.
      */
      not: BaseMatchers<Promise<void>, T>;
   };
-  extend(matchers: any): void;
+  extend<MoreMatchers extends Record<string, (this: State, receiver: any, ...args: any[]) => MatcherReturnType | Promise<MatcherReturnType>>>(matchers: MoreMatchers): Expect<ExtendedMatchers & MoreMatchers>;
   configure: (configuration: {
     message?: string,
     timeout?: number,
     soft?: boolean,
-  }) => Expect;
+  }) => Expect<ExtendedMatchers>;
   getState(): {
     expand?: boolean;
     isNot?: boolean;
@@ -399,7 +442,7 @@ export const test: TestType<PlaywrightTestArgs & PlaywrightTestOptions, Playwrig
 export default test;
 
 export const _baseTest: TestType<{}, {}>;
-export const expect: Expect;
+export const expect: Expect<{}>;
 
 /**
  * Defines Playwright config