diff --git a/packages/playwright-core/src/server/bidi/bidiChromium.ts b/packages/playwright-core/src/server/bidi/bidiChromium.ts
index 364f81b3c4..57506a4571 100644
--- a/packages/playwright-core/src/server/bidi/bidiChromium.ts
+++ b/packages/playwright-core/src/server/bidi/bidiChromium.ts
@@ -21,6 +21,7 @@ import { BrowserReadyState, BrowserType, kNoXServerRunningError } from '../brows
 import { BidiBrowser } from './bidiBrowser';
 import { kBrowserCloseMessageId } from './bidiConnection';
 import { chromiumSwitches } from '../chromium/chromiumSwitches';
+import { RecentLogsCollector } from '../utils/debugLogger';
 
 import type { BrowserOptions } from '../browser';
 import type { SdkObject } from '../instrumentation';
@@ -35,13 +36,23 @@ export class BidiChromium extends BrowserType {
     super(parent, 'bidi');
   }
 
-  override async connectToTransport(transport: ConnectionTransport, options: BrowserOptions): Promise<BidiBrowser> {
+  override async connectToTransport(transport: ConnectionTransport, options: BrowserOptions, browserLogsCollector: RecentLogsCollector): Promise<BidiBrowser> {
     // Chrome doesn't support Bidi, we create Bidi over CDP which is used by Chrome driver.
     // bidiOverCdp depends on chromium-bidi which we only have in devDependencies, so
     // we load bidiOverCdp dynamically.
     const bidiTransport = await require('./bidiOverCdp').connectBidiOverCdp(transport);
     (transport as any)[kBidiOverCdpWrapper] = bidiTransport;
-    return BidiBrowser.connect(this.attribution.playwright, bidiTransport, options);
+    try {
+      return BidiBrowser.connect(this.attribution.playwright, bidiTransport, options);
+    } catch (e) {
+      if (browserLogsCollector.recentLogs().some(log => log.includes('Failed to create a ProcessSingleton for your profile directory.'))) {
+        throw new Error(
+            'Failed to create a ProcessSingleton for your profile directory. ' +
+            'This usually means that the profile is already in use by another instance of Chromium.'
+        );
+      }
+      throw e;
+    }
   }
 
   override doRewriteStartupLog(error: ProtocolError): ProtocolError {
@@ -155,6 +166,10 @@ export class BidiChromium extends BrowserType {
 
 class ChromiumReadyState extends BrowserReadyState {
   override onBrowserOutput(message: string): void {
+    if (message.includes('Failed to create a ProcessSingleton for your profile directory.')) {
+      this._wsEndpoint.reject(new Error('Failed to create a ProcessSingleton for your profile directory. ' +
+        'This usually means that the profile is already in use by another instance of Chromium.'));
+    }
     const match = message.match(/DevTools listening on (.*)/);
     if (match)
       this._wsEndpoint.resolve(match[1]);
diff --git a/packages/playwright-core/src/server/browserType.ts b/packages/playwright-core/src/server/browserType.ts
index 45e99ce75d..4a8600c557 100644
--- a/packages/playwright-core/src/server/browserType.ts
+++ b/packages/playwright-core/src/server/browserType.ts
@@ -157,7 +157,7 @@ export abstract class BrowserType extends SdkObject {
     if (persistent)
       validateBrowserContextOptions(persistent, browserOptions);
     copyTestHooks(options, browserOptions);
-    const browser = await this.connectToTransport(transport, browserOptions);
+    const browser = await this.connectToTransport(transport, browserOptions, browserLogsCollector);
     (browser as any)._userDataDirForTest = userDataDir;
     // We assume no control when using custom arguments, and do not prepare the default context in that case.
     if (persistent && !options.ignoreAllDefaultArgs)
@@ -342,7 +342,7 @@ export abstract class BrowserType extends SdkObject {
   }
 
   abstract defaultArgs(options: types.LaunchOptions, isPersistent: boolean, userDataDir: string): string[];
-  abstract connectToTransport(transport: ConnectionTransport, options: BrowserOptions): Promise<Browser>;
+  abstract connectToTransport(transport: ConnectionTransport, options: BrowserOptions, browserLogsCollector: RecentLogsCollector): Promise<Browser>;
   abstract amendEnvironment(env: Env, userDataDir: string, executable: string, browserArguments: string[]): Env;
   abstract doRewriteStartupLog(error: ProtocolError): ProtocolError;
   abstract attemptToGracefullyCloseBrowser(transport: ConnectionTransport): void;
diff --git a/packages/playwright-core/src/server/chromium/chromium.ts b/packages/playwright-core/src/server/chromium/chromium.ts
index 6adef73807..91f4fd6f9b 100644
--- a/packages/playwright-core/src/server/chromium/chromium.ts
+++ b/packages/playwright-core/src/server/chromium/chromium.ts
@@ -126,13 +126,23 @@ export class Chromium extends BrowserType {
     return directory ? new CRDevTools(path.join(directory, 'devtools-preferences.json')) : undefined;
   }
 
-  override async connectToTransport(transport: ConnectionTransport, options: BrowserOptions): Promise<CRBrowser> {
+  override async connectToTransport(transport: ConnectionTransport, options: BrowserOptions, browserLogsCollector: RecentLogsCollector): Promise<CRBrowser> {
     let devtools = this._devtools;
     if ((options as any).__testHookForDevTools) {
       devtools = this._createDevTools();
       await (options as any).__testHookForDevTools(devtools);
     }
-    return CRBrowser.connect(this.attribution.playwright, transport, options, devtools);
+    try {
+      return await CRBrowser.connect(this.attribution.playwright, transport, options, devtools);
+    } catch (e) {
+      if (browserLogsCollector.recentLogs().some(log => log.includes('Failed to create a ProcessSingleton for your profile directory.'))) {
+        throw new Error(
+            'Failed to create a ProcessSingleton for your profile directory. ' +
+            'This usually means that the profile is already in use by another instance of Chromium.'
+        );
+      }
+      throw e;
+    }
   }
 
   override doRewriteStartupLog(error: ProtocolError): ProtocolError {
@@ -358,6 +368,10 @@ export class Chromium extends BrowserType {
 
 class ChromiumReadyState extends BrowserReadyState {
   override onBrowserOutput(message: string): void {
+    if (message.includes('Failed to create a ProcessSingleton for your profile directory.')) {
+      this._wsEndpoint.reject(new Error('Failed to create a ProcessSingleton for your profile directory. ' +
+        'This usually means that the profile is already in use by another instance of Chromium.'));
+    }
     const match = message.match(/DevTools listening on (.*)/);
     if (match)
       this._wsEndpoint.resolve(match[1]);
diff --git a/tests/library/chromium/chromium.spec.ts b/tests/library/chromium/chromium.spec.ts
index 910e0830ff..f254ad3cf0 100644
--- a/tests/library/chromium/chromium.spec.ts
+++ b/tests/library/chromium/chromium.spec.ts
@@ -630,3 +630,33 @@ test.describe('PW_EXPERIMENTAL_SERVICE_WORKER_NETWORK_EVENTS=1', () => {
     expect(req.headers['x-custom-header']).toBe('custom!');
   });
 });
+
+test('should throw when connecting twice to an already running persistent context (--remote-debugging-port)', async ({ browserType, createUserDataDir, platform, isHeadlessShell }) => {
+  test.skip(isHeadlessShell, 'Headless shell does not create a ProcessSingleton');
+  test.fixme(platform === 'win32', 'Windows does not print something to the console when the profile is already in use by another instance of Chromium.');
+  const userDataDir = await createUserDataDir();
+  const browser = await browserType.launchPersistentContext(userDataDir, {
+    cdpPort: 9222,
+  } as any);
+  try {
+    const error = await browserType.launchPersistentContext(userDataDir, {
+      cdpPort: 9223,
+    } as any).catch(e => e);
+    expect(error.message).toContain('This usually means that the profile is already in use by another instance of Chromium.');
+  } finally {
+    await browser.close();
+  }
+});
+
+test('should throw when connecting twice to an already running persistent context (--remote-debugging-pipe)', async ({ browserType, createUserDataDir, platform, isHeadlessShell }) => {
+  test.skip(isHeadlessShell, 'Headless shell does not create a ProcessSingleton');
+  test.fixme(platform === 'win32', 'Windows does not print something to the console when the profile is already in use by another instance of Chromium.');
+  const userDataDir = await createUserDataDir();
+  const browser = await browserType.launchPersistentContext(userDataDir);
+  try {
+    const error = await browserType.launchPersistentContext(userDataDir).catch(e => e);
+    expect(error.message).toContain('This usually means that the profile is already in use by another instance of Chromium.');
+  } finally {
+    await browser.close();
+  }
+});