diff --git a/packages/playwright/src/matchers/expect.ts b/packages/playwright/src/matchers/expect.ts
index 9c426fd86e..7a36b98050 100644
--- a/packages/playwright/src/matchers/expect.ts
+++ b/packages/playwright/src/matchers/expect.ts
@@ -290,7 +290,7 @@ class ExpectMetaInfoProxyHandler implements ProxyHandler<any> {
     if (this._info.isPoll) {
       if ((customAsyncMatchers as any)[matcherName] || matcherName === 'resolves' || matcherName === 'rejects')
         throw new Error(`\`expect.poll()\` does not support "${matcherName}" matcher.`);
-      matcher = (...args: any[]) => pollMatcher(resolvedMatcherName, !!this._info.isNot, this._info.pollIntervals, this._info.pollTimeout ?? currentExpectTimeout(), this._info.generator!, ...args);
+      matcher = (...args: any[]) => pollMatcher(resolvedMatcherName, this._info, this._prefix, ...args);
     }
     return (...args: any[]) => {
       const testInfo = currentTestInfo();
@@ -350,25 +350,34 @@ class ExpectMetaInfoProxyHandler implements ProxyHandler<any> {
   }
 }
 
-async function pollMatcher(qualifiedMatcherName: any, isNot: boolean, pollIntervals: number[] | undefined, timeout: number, generator: () => any, ...args: any[]) {
+async function pollMatcher(qualifiedMatcherName: string, info: ExpectMetaInfo, prefix: string[], ...args: any[]) {
   const testInfo = currentTestInfo();
+  const timeout = info.pollTimeout ?? currentExpectTimeout();
   const { deadline, timeoutMessage } = testInfo ? testInfo._deadlineForMatcher(timeout) : TestInfoImpl._defaultDeadlineForMatcher(timeout);
 
   const result = await pollAgainstDeadline<Error|undefined>(async () => {
     if (testInfo && currentTestInfo() !== testInfo)
       return { continuePolling: false, result: undefined };
 
-    const value = await generator();
-    let expectInstance = expectLibrary(value) as any;
-    if (isNot)
-      expectInstance = expectInstance.not;
+    const innerInfo: ExpectMetaInfo = {
+      ...info,
+      isSoft: false, // soft is outside of poll, not inside
+      isPoll: false,
+      pollTimeout: undefined,
+      pollIntervals: undefined,
+      generator: undefined,
+    };
+    const value = await info.generator!();
     try {
-      expectInstance[qualifiedMatcherName].call(expectInstance, ...args);
+      let matchers = createMatchers(value, innerInfo, prefix);
+      if (info.isNot)
+        matchers = matchers.not;
+      matchers[qualifiedMatcherName](...args);
       return { continuePolling: false, result: undefined };
     } catch (error) {
       return { continuePolling: true, result: error };
     }
-  }, deadline, pollIntervals ?? [100, 250, 500, 1000]);
+  }, deadline, info.pollIntervals ?? [100, 250, 500, 1000]);
 
   if (result.timedOut) {
     const message = result.result ? [
diff --git a/tests/playwright-test/expect-poll.spec.ts b/tests/playwright-test/expect-poll.spec.ts
index 344fdccdee..208ac4ccce 100644
--- a/tests/playwright-test/expect-poll.spec.ts
+++ b/tests/playwright-test/expect-poll.spec.ts
@@ -262,4 +262,20 @@ test('should propagate string exception from async arrow function', { annotation
   });
 
   expect(result.output).toContain('some error');
-});
\ No newline at end of file
+});
+
+test('should show custom message', {
+  annotation: { type: 'issue', description: 'https://github.com/microsoft/playwright/issues/32582' }
+}, async ({ runInlineTest }) => {
+  const result = await runInlineTest({
+    'a.spec.ts': `
+      import { test, expect } from '@playwright/test';
+      test('should fail', async () => {
+        await expect.poll(() => 1, { message: 'custom message', timeout: 500 }).toBe(2);
+      });
+    `,
+  });
+  expect(result.output).toContain('Error: custom message');
+  expect(result.output).toContain('Expected: 2');
+  expect(result.output).toContain('Received: 1');
+});
diff --git a/tests/playwright-test/test-step.spec.ts b/tests/playwright-test/test-step.spec.ts
index 96539a4c88..d14bccd98b 100644
--- a/tests/playwright-test/test-step.spec.ts
+++ b/tests/playwright-test/test-step.spec.ts
@@ -987,9 +987,12 @@ expect    |expect.poll.toHaveLength @ a.test.ts:14
 pw:api    |  page.goto(about:blank) @ a.test.ts:7
 test.step |  inner step attempt: 0 @ a.test.ts:8
 expect    |    expect.toBe @ a.test.ts:10
+expect    |  expect.toHaveLength @ a.test.ts:6
+expect    |  ↪ error: Error: expect(received).toHaveLength(expected)
 pw:api    |  page.goto(about:blank) @ a.test.ts:7
 test.step |  inner step attempt: 1 @ a.test.ts:8
 expect    |    expect.toBe @ a.test.ts:10
+expect    |  expect.toHaveLength @ a.test.ts:6
 hook      |After Hooks
 fixture   |  fixture: page
 fixture   |  fixture: context
@@ -1036,9 +1039,12 @@ expect    |expect.poll.toBe @ a.test.ts:13
 expect    |  expect.toHaveText @ a.test.ts:7
 test.step |  iteration 1 @ a.test.ts:9
 expect    |    expect.toBeVisible @ a.test.ts:10
+expect    |  expect.toBe @ a.test.ts:6
+expect    |  ↪ error: Error: expect(received).toBe(expected) // Object.is equality
 expect    |  expect.toHaveText @ a.test.ts:7
 test.step |  iteration 2 @ a.test.ts:9
 expect    |    expect.toBeVisible @ a.test.ts:10
+expect    |  expect.toBe @ a.test.ts:6
 hook      |After Hooks
 fixture   |  fixture: page
 fixture   |  fixture: context