diff --git a/src/bot/orchestrator.ts b/src/bot/orchestrator.ts
index dd8deec..a704bb7 100644
--- a/src/bot/orchestrator.ts
+++ b/src/bot/orchestrator.ts
@@ -91,7 +91,7 @@ export class BotOrchestrator {
       throw new Error(`Invalid meeting URL: ${this._meetingUrl}`);
     }
 
-    const isAuthenticated = !!(this._options.botAccountEmail && this._options.botAccountPassword);
+    let useAuthentication = !!(this._options.botAccountEmail && this._options.botAccountPassword);
 
     try {
       this._setState('launching');
@@ -99,61 +99,24 @@ export class BotOrchestrator {
       // Connect to Gateway WebSocket first
       await this._connectToGateway();
 
-      // Launch browser
-      await this._launchBrowser();
-
-      // Authenticate with Microsoft if bot account is configured
-      if (isAuthenticated) {
-        const { AuthProcedure } = await import('./authProcedure');
-        const authProcedure = new AuthProcedure(this._page!, this._logger);
-        const authSuccess = await authProcedure.authenticateWithMicrosoft(
-          this._options.botAccountEmail!,
-          this._options.botAccountPassword!
-        );
-        if (!authSuccess) {
-          this._logger.warn('Microsoft authentication failed - falling back to anonymous join');
-        }
-      }
-
-      this._setState('navigating');
-
-      // Navigate to meeting and handle launcher
-      await this._joinProcedure!.startMeetingLauncherFlow(this._meetingUrl);
-
-      // Set virtual background if configured (must be done on pre-join screen, before "Join now")
-      if (this._options.backgroundImageUrl && this._page) {
-        try {
-          const { BackgroundProcedure } = await import('./backgroundProcedure');
-          const bgProcedure = new BackgroundProcedure(this._page, this._logger);
-          await bgProcedure.setBackgroundFromUrl(this._options.backgroundImageUrl);
-        } catch (error) {
-          this._logger.warn(`Background image setup failed (non-fatal): ${error}`);
-        }
-      }
-
-      // Join the meeting (enter lobby for anonymous, direct join for authenticated)
-      await this._joinProcedure!.joinMeetingLobbyFlow();
-
-      // Check if we're in lobby
-      const inLobby = await this._joinProcedure!.isInMeetingLobby({ waitForSeconds: 10 });
-      if (inLobby) {
-        this._setState('in_lobby');
-        this._logger.info('Bot is in lobby, waiting to be admitted...');
-      }
-
-      // Wait to be admitted to the meeting
-      await this._waitForMeetingAdmission();
-
-      this._setState('in_meeting');
-      this._logger.info('Bot joined the meeting!');
-
-      // Initialize audio
-      await this._audioProcedure!.initialize();
-
-      // Enable and subscribe to captions
-      await this._enableCaptions();
+      // Try joining (authenticated first, then anonymous fallback)
+      await this._attemptJoin(useAuthentication);
 
     } catch (error) {
+      // If authenticated join failed, retry as anonymous
+      if (useAuthentication) {
+        this._logger.warn(`Authenticated join failed: ${(error as Error).message}. Retrying as anonymous guest...`);
+        try {
+          await this._cleanup();
+          await this._attemptJoin(false);
+          return;
+        } catch (retryError) {
+          this._logger.error('Anonymous fallback also failed:', retryError);
+          this._setState('error', (retryError as Error).message);
+          await this._takeScreenshot('error-fallback');
+          throw retryError;
+        }
+      }
       this._logger.error('Error starting bot:', error);
       this._setState('error', (error as Error).message);
       await this._takeScreenshot('error');
@@ -161,6 +124,87 @@ export class BotOrchestrator {
     }
   }
 
+  /**
+   * Attempt to join a meeting (authenticated or anonymous).
+   */
+  private async _attemptJoin(authenticate: boolean): Promise<void> {
+    // Launch browser
+    await this._launchBrowser();
+
+    // Authenticate with Microsoft if requested
+    if (authenticate) {
+      const { AuthProcedure } = await import('./authProcedure');
+      const authProcedure = new AuthProcedure(this._page!, this._logger);
+      const authSuccess = await authProcedure.authenticateWithMicrosoft(
+        this._options.botAccountEmail!,
+        this._options.botAccountPassword!
+      );
+      if (!authSuccess) {
+        throw new Error('Microsoft authentication failed');
+      }
+    }
+
+    // Update JoinProcedure with correct auth state
+    this._joinProcedure = new JoinProcedure(this._page!, this._logger, this._botName, authenticate);
+
+    this._setState('navigating');
+
+    // Navigate to meeting and handle launcher
+    await this._joinProcedure.startMeetingLauncherFlow(this._meetingUrl);
+
+    // Set virtual background if configured (must be done on pre-join screen, before "Join now")
+    if (this._options.backgroundImageUrl && this._page && authenticate) {
+      try {
+        const { BackgroundProcedure } = await import('./backgroundProcedure');
+        const bgProcedure = new BackgroundProcedure(this._page, this._logger);
+        await bgProcedure.setBackgroundFromUrl(this._options.backgroundImageUrl);
+      } catch (error) {
+        this._logger.warn(`Background image setup failed (non-fatal): ${error}`);
+      }
+    }
+
+    // Join the meeting
+    await this._joinProcedure.joinMeetingLobbyFlow();
+
+    // Check if we're in lobby
+    const inLobby = await this._joinProcedure.isInMeetingLobby({ waitForSeconds: 10 });
+    if (inLobby) {
+      this._setState('in_lobby');
+      this._logger.info('Bot is in lobby, waiting to be admitted...');
+    }
+
+    // Wait to be admitted to the meeting
+    await this._waitForMeetingAdmission();
+
+    this._setState('in_meeting');
+    this._logger.info(`Bot joined the meeting! (authenticated: ${authenticate})`);
+
+    // Initialize audio
+    await this._audioProcedure!.initialize();
+
+    // Enable and subscribe to captions
+    await this._enableCaptions();
+  }
+
+  /**
+   * Clean up browser for retry (close browser without full shutdown).
+   */
+  private async _cleanup(): Promise<void> {
+    try {
+      if (this._page) await this._page.close().catch(() => {});
+      if (this._context) await this._context.close().catch(() => {});
+      if (this._browser) await this._browser.close().catch(() => {});
+      this._page = null;
+      this._context = null;
+      this._browser = null;
+      this._joinProcedure = null;
+      this._captionsProcedure = null;
+      this._audioProcedure = null;
+    } catch {
+      // Ignore cleanup errors
+    }
+  }
+
   /**
    * Connect to the Gateway WebSocket for this session.
    */