diff --git a/packages/playwright-core/src/client/browserType.ts b/packages/playwright-core/src/client/browserType.ts
index 1a8f02c879..d002fb5197 100644
--- a/packages/playwright-core/src/client/browserType.ts
+++ b/packages/playwright-core/src/client/browserType.ts
@@ -28,7 +28,6 @@ import type * as api from '../../types/types';
 import { kBrowserClosedError } from '../common/errors';
 import { raceAgainstTimeout } from '../utils/timeoutRunner';
 import type { Playwright } from './playwright';
-import { debugLogger } from '../common/debugLogger';
 
 export interface BrowserServerLauncher {
   launchServer(options?: LaunchServerOptions): Promise<api.BrowserServer>;
@@ -200,10 +199,6 @@ export class BrowserType extends ChannelOwner<channels.BrowserTypeChannel> imple
         this._didLaunchBrowser(browser, {}, logger);
         browser._shouldCloseConnectionOnClose = true;
         browser._connectHeaders = connectHeaders;
-        for (const header of connectHeaders) {
-          if (header.name === 'x-playwright-debug-log')
-            debugLogger.log('browser', header.value);
-        }
         browser.on(Events.Browser.Disconnected, closePipe);
         return browser;
       }, deadline ? deadline - monotonicTime() : 0);
diff --git a/packages/playwright-core/src/server/dispatchers/localUtilsDispatcher.ts b/packages/playwright-core/src/server/dispatchers/localUtilsDispatcher.ts
index 191f31636c..25ba643015 100644
--- a/packages/playwright-core/src/server/dispatchers/localUtilsDispatcher.ts
+++ b/packages/playwright-core/src/server/dispatchers/localUtilsDispatcher.ts
@@ -202,7 +202,7 @@ export class LocalUtilsDispatcher extends Dispatcher<{ guid: string }, channels.
       };
       const wsEndpoint = await urlToWSEndpoint(progress, params.wsEndpoint);
 
-      const transport = await WebSocketTransport.connect(progress, wsEndpoint, wsHeaders, true);
+      const transport = await WebSocketTransport.connect(progress, wsEndpoint, wsHeaders, true, 'x-playwright-debug-log');
       const socksInterceptor = new SocksInterceptor(transport, params.exposeNetwork, params.socksProxyRedirectPortForTest);
       const pipe = new JsonPipeDispatcher(this);
       transport.onmessage = json => {
diff --git a/packages/playwright-core/src/server/transport.ts b/packages/playwright-core/src/server/transport.ts
index c9b9e96d3d..a7dbb7deff 100644
--- a/packages/playwright-core/src/server/transport.ts
+++ b/packages/playwright-core/src/server/transport.ts
@@ -58,10 +58,10 @@ export class WebSocketTransport implements ConnectionTransport {
   readonly wsEndpoint: string;
   readonly headers: HeadersArray = [];
 
-  static async connect(progress: (Progress|undefined), url: string, headers?: { [key: string]: string; }, followRedirects?: boolean): Promise<WebSocketTransport> {
+  static async connect(progress: (Progress|undefined), url: string, headers?: { [key: string]: string; }, followRedirects?: boolean, debugLogHeader?: string): Promise<WebSocketTransport> {
     const logUrl = stripQueryParams(url);
     progress?.log(`<ws connecting> ${logUrl}`);
-    const transport = new WebSocketTransport(progress, url, logUrl, headers, followRedirects);
+    const transport = new WebSocketTransport(progress, url, logUrl, headers, followRedirects, debugLogHeader);
     let success = false;
     progress?.cleanupWhenAborted(async () => {
       if (!success)
@@ -78,6 +78,10 @@ export class WebSocketTransport implements ConnectionTransport {
         transport._ws.close();
       });
       transport._ws.on('unexpected-response', (request: ClientRequest, response: IncomingMessage) => {
+        for (let i = 0; i < response.rawHeaders.length; i += 2) {
+          if (debugLogHeader && response.rawHeaders[i] === debugLogHeader)
+            progress?.log(response.rawHeaders[i + 1]);
+        }
         const chunks: Buffer[] = [];
         const errorPrefix = `${logUrl} ${response.statusCode} ${response.statusMessage}`;
         response.on('data', chunk => chunks.push(chunk));
@@ -93,7 +97,7 @@ export class WebSocketTransport implements ConnectionTransport {
     return transport;
   }
 
-  constructor(progress: Progress|undefined, url: string, logUrl: string, headers?: { [key: string]: string; }, followRedirects?: boolean) {
+  constructor(progress: Progress|undefined, url: string, logUrl: string, headers?: { [key: string]: string; }, followRedirects?: boolean, debugLogHeader?: string) {
     this.wsEndpoint = url;
     this._logUrl = logUrl;
     this._ws = new ws(url, [], {
@@ -105,9 +109,12 @@ export class WebSocketTransport implements ConnectionTransport {
       followRedirects,
       agent: (/^(https|wss):\/\//.test(url)) ? httpsHappyEyeballsAgent : httpHappyEyeballsAgent
     });
-    this._ws.on('upgrade', request => {
-      for (let i = 0; i < request.rawHeaders.length; i += 2)
-        this.headers.push({ name: request.rawHeaders[i], value: request.rawHeaders[i + 1] });
+    this._ws.on('upgrade', response => {
+      for (let i = 0; i < response.rawHeaders.length; i += 2) {
+        this.headers.push({ name: response.rawHeaders[i], value: response.rawHeaders[i + 1] });
+        if (debugLogHeader && response.rawHeaders[i] === debugLogHeader)
+          progress?.log(response.rawHeaders[i + 1]);
+      }
     });
     this._progress = progress;
     // The 'ws' module in node sometimes sends us multiple messages in a single task.
diff --git a/tests/playwright-test/playwright.connect.spec.ts b/tests/playwright-test/playwright.connect.spec.ts
index 35b803e514..d73344ab9c 100644
--- a/tests/playwright-test/playwright.connect.spec.ts
+++ b/tests/playwright-test/playwright.connect.spec.ts
@@ -117,3 +117,44 @@ test('should respect connectOptions.timeout', async ({ runInlineTest }) => {
   expect(result.passed).toBe(0);
   expect(result.output).toContain('browserType.launch: Timeout 1ms exceeded.');
 });
+
+test('should print debug log when failed to connect', async ({ runInlineTest }) => {
+  const result = await runInlineTest({
+    'playwright.config.js': `
+      module.exports = {
+        globalSetup: './global-setup',
+        use: {
+          connectOptions: {
+            wsEndpoint: process.env.CONNECT_WS_ENDPOINT,
+          },
+        },
+      };
+    `,
+    'global-setup.ts': `
+      import { chromium } from '@playwright/test';
+      import ws from 'ws';
+      import http from 'http';
+      module.exports = async () => {
+        const server = http.createServer(() => {});
+        server.on('upgrade', async (request, socket, head) => {
+          socket.write('HTTP/1.1 401 Unauthorized\\r\\nx-playwright-debug-log: b-debug-log-string\\r\\n\\r\\nUnauthorized body');
+          socket.destroy();
+        });
+        server.listen(0);
+        await new Promise(f => server.once('listening', f));
+        process.env.CONNECT_WS_ENDPOINT = 'ws://localhost:' + server.address().port;
+        return () => new Promise(f => server.close(f));
+      };
+    `,
+    'a.test.ts': `
+      import { test, expect } from '@playwright/test';
+      test('fail', async ({ page }) => {
+        await page.setContent('<div>FAIL</div>');
+      });
+    `,
+  });
+  expect(result.exitCode).toBe(1);
+  expect(result.failed).toBe(1);
+  expect(result.output).toContain('b-debug-log-string');
+  expect(result.results[0].attachments).toEqual([]);
+});