diff --git a/packages/playwright-core/src/server/frames.ts b/packages/playwright-core/src/server/frames.ts
index bd288ed04d..26c30b4c40 100644
--- a/packages/playwright-core/src/server/frames.ts
+++ b/packages/playwright-core/src/server/frames.ts
@@ -1406,7 +1406,7 @@ export class Frame extends SdkObject {
           // expect(locator).not.conditionThatDoesMatch
           progress.setIntermediateResult(result.received);
           if (!Array.isArray(result.received))
-            progress.log(`  unexpected value "${result.received}"`);
+            progress.log(`  unexpected value "${progress.injectedScript.renderUnexpectedValue(options.expression, result.received)}"`);
           return progress.continuePolling;
         }
 
diff --git a/packages/playwright-core/src/server/injected/injectedScript.ts b/packages/playwright-core/src/server/injected/injectedScript.ts
index 8e762d0226..c1c4200c9f 100644
--- a/packages/playwright-core/src/server/injected/injectedScript.ts
+++ b/packages/playwright-core/src/server/injected/injectedScript.ts
@@ -1205,6 +1205,30 @@ export class InjectedScript {
     throw this.createStacklessError('Unknown expect matcher: ' + expression);
   }
 
+  renderUnexpectedValue(expression: string, received: any): string {
+    if (expression === 'to.be.checked')
+      return received ? 'checked' : 'unchecked';
+    if (expression === 'to.be.unchecked')
+      return received ? 'unchecked' : 'checked';
+    if (expression === 'to.be.visible')
+      return received ? 'visible' : 'hidden';
+    if (expression === 'to.be.hidden')
+      return received ? 'hidden' : 'visible';
+    if (expression === 'to.be.enabled')
+      return received ? 'enabled' : 'disabled';
+    if (expression === 'to.be.disabled')
+      return received ? 'disabled' : 'enabled';
+    if (expression === 'to.be.editable')
+      return received ? 'editable' : 'readonly';
+    if (expression === 'to.be.readonly')
+      return received ? 'readonly' : 'editable';
+    if (expression === 'to.be.empty')
+      return received ? 'empty' : 'not empty';
+    if (expression === 'to.be.focused')
+      return received ? 'focused' : 'not focused';
+    return received;
+  }
+
   expectArray(elements: Element[], options: FrameExpectParams): { matches: boolean, received?: any } {
     const expression = options.expression;
 
diff --git a/tests/page/expect-boolean.spec.ts b/tests/page/expect-boolean.spec.ts
index 92e1dfe776..8b9e325b5e 100644
--- a/tests/page/expect-boolean.spec.ts
+++ b/tests/page/expect-boolean.spec.ts
@@ -86,6 +86,16 @@ test.describe('toBeChecked', () => {
       });
     }
   });
+
+  test('friendly log', async ({ page }) => {
+    await page.setContent('<input type=checkbox></input>');
+    const message1 = await expect(page.locator('input')).toBeChecked({ timeout: 1000 }).catch(e => e.message);
+    expect(message1).toContain('unexpected value "unchecked"');
+
+    await page.setContent('<input type=checkbox checked></input>');
+    const message2 = await expect(page.locator('input')).toBeChecked({ checked: false, timeout: 1000 }).catch(e => e.message);
+    expect(message2).toContain('unexpected value "checked"');
+  });
 });
 
 test.describe('toBeEditable', () => {