diff --git a/src/__tests__/renderer/components/TabBar.test.tsx b/src/__tests__/renderer/components/TabBar.test.tsx
index 6ecce586..497a12e9 100644
--- a/src/__tests__/renderer/components/TabBar.test.tsx
+++ b/src/__tests__/renderer/components/TabBar.test.tsx
@@ -1512,7 +1512,8 @@ describe('TabBar', () => {
       expect(inactiveTab.style.backgroundColor).not.toBe('rgba(255, 255, 255, 0.08)');
     });
 
-    it('sets tab title attribute', () => {
+    it('does not set title attribute on tabs (removed for cleaner UX)', () => {
+      // Tab title tooltips were intentionally removed to streamline the tab interaction feel
       const tabs = [createTab({
         id: 'tab-1',
         name: 'My Tab',
@@ -1531,51 +1532,7 @@ describe('TabBar', () => {
       );
 
       const tab = screen.getByText('My Tab').closest('[data-tab-id]')!;
-      expect(tab).toHaveAttribute('title', 'My Tab');
-    });
-
-    it('uses agentSessionId for title when no name', () => {
-      const tabs = [createTab({
-        id: 'tab-1',
-        name: '',
-        agentSessionId: 'session-123-abc'
-      })];
-
-      render(
-        <TabBar
-          tabs={tabs}
-          activeTabId="tab-1"
-          theme={mockTheme}
-          onTabSelect={mockOnTabSelect}
-          onTabClose={mockOnTabClose}
-          onNewTab={mockOnNewTab}
-        />
-      );
-
-      const tab = screen.getByText('SESSION').closest('[data-tab-id]')!;
-      expect(tab).toHaveAttribute('title', 'session-123-abc');
-    });
-
-    it('uses "New tab" for title when no name or agentSessionId', () => {
-      const tabs = [createTab({
-        id: 'tab-1',
-        name: '',
-        agentSessionId: undefined
-      })];
-
-      render(
-        <TabBar
-          tabs={tabs}
-          activeTabId="tab-1"
-          theme={mockTheme}
-          onTabSelect={mockOnTabSelect}
-          onTabClose={mockOnTabClose}
-          onNewTab={mockOnNewTab}
-        />
-      );
-
-      const tab = screen.getByText('New Session').closest('[data-tab-id]')!;
-      expect(tab).toHaveAttribute('title', 'New tab');
+      expect(tab).not.toHaveAttribute('title');
     });
   });
 
diff --git a/src/__tests__/renderer/contexts/ToastContext.test.tsx b/src/__tests__/renderer/contexts/ToastContext.test.tsx
index d7987377..6dbdb81c 100644
--- a/src/__tests__/renderer/contexts/ToastContext.test.tsx
+++ b/src/__tests__/renderer/contexts/ToastContext.test.tsx
@@ -233,6 +233,7 @@ describe('ToastContext', () => {
         taskDuration: 5000,
         agentSessionId: 'test-session-id',
         tabName: 'TestTab',
+        audioNotification: { enabled: false },
       });
     });
 
diff --git a/src/main/index.ts b/src/main/index.ts
index 224d0c04..50fe18c8 100644
--- a/src/main/index.ts
+++ b/src/main/index.ts
@@ -32,6 +32,31 @@ interface BootstrapSettings {
   iCloudSyncEnabled?: boolean; // Legacy - kept for backwards compatibility during migration
 }
 
+// ============================================================================
+// Data Directory Configuration (MUST happen before any Store initialization)
+// ============================================================================
+const isDevelopment = process.env.NODE_ENV === 'development';
+
+// Demo mode: use a separate data directory for fresh demos
+if (DEMO_MODE) {
+  app.setPath('userData', DEMO_DATA_PATH);
+  console.log(`[DEMO MODE] Using data directory: ${DEMO_DATA_PATH}`);
+}
+
+// Development mode: use a separate data directory to allow running alongside production
+// This prevents database lock conflicts (e.g., Service Worker storage)
+// Set USE_PROD_DATA=1 to use the production data directory instead (requires closing production app)
+if (isDevelopment && !DEMO_MODE && !process.env.USE_PROD_DATA) {
+  const devDataPath = path.join(app.getPath('userData'), '..', 'maestro-dev');
+  app.setPath('userData', devDataPath);
+  console.log(`[DEV MODE] Using data directory: ${devDataPath}`);
+} else if (isDevelopment && process.env.USE_PROD_DATA) {
+  console.log(`[DEV MODE] Using production data directory: ${app.getPath('userData')}`);
+}
+
+// ============================================================================
+// Store Initialization (after userData path is configured)
+// ============================================================================
 const bootstrapStore = new Store<BootstrapSettings>({
   name: 'maestro-bootstrap',
   defaults: {},
@@ -62,12 +87,11 @@ function getSyncPath(): string | undefined {
 }
 
 // Get the sync path once at startup
-const syncPath = getSyncPath();
+// If no custom sync path, use the (potentially modified) userData path
+const syncPath = getSyncPath() || app.getPath('userData');
 
-// Initialize Sentry for crash reporting (before app.ready)
+// Initialize Sentry for crash reporting
 // Only enable in production - skip during development to avoid noise from hot-reload artifacts
-const isDevelopment = process.env.NODE_ENV === 'development';
-
 // Check if crash reporting is enabled (default: true for opt-out behavior)
 const crashReportingStore = new Store<{ crashReportingEnabled: boolean }>({
   name: 'maestro-settings',
@@ -93,23 +117,6 @@ if (crashReportingEnabled && !isDevelopment) {
   });
 }
 
-// Demo mode: use a separate data directory for fresh demos
-if (DEMO_MODE) {
-  app.setPath('userData', DEMO_DATA_PATH);
-  console.log(`[DEMO MODE] Using data directory: ${DEMO_DATA_PATH}`);
-}
-
-// Development mode: use a separate data directory to allow running alongside production
-// This prevents database lock conflicts (e.g., Service Worker storage)
-// Set USE_PROD_DATA=1 to use the production data directory instead (requires closing production app)
-if (isDevelopment && !DEMO_MODE && !process.env.USE_PROD_DATA) {
-  const devDataPath = path.join(app.getPath('userData'), '..', 'maestro-dev');
-  app.setPath('userData', devDataPath);
-  console.log(`[DEV MODE] Using data directory: ${devDataPath}`);
-} else if (isDevelopment && process.env.USE_PROD_DATA) {
-  console.log(`[DEV MODE] Using production data directory: ${app.getPath('userData')}`);
-}
-
 // Type definitions
 interface MaestroSettings {
   activeThemeId: string;
@@ -1405,8 +1412,17 @@ function setupIpcHandlers() {
             logger.error('TTS stdin error', 'TTS', { error: String(err), code: errorCode });
           }
         });
-        child.stdin.write(text);
-        child.stdin.end();
+        console.log('[TTS Main] Writing to stdin:', text);
+        child.stdin.write(text, 'utf8', (err) => {
+          if (err) {
+            console.error('[TTS Main] stdin write error:', err);
+          } else {
+            console.log('[TTS Main] stdin write completed, ending stream');
+          }
+          child.stdin!.end();
+        });
+      } else {
+        console.error('[TTS Main] No stdin available on child process');
       }
 
       child.on('error', (err) => {
diff --git a/src/renderer/components/FilePreview.tsx b/src/renderer/components/FilePreview.tsx
index 18952628..2ae03802 100644
--- a/src/renderer/components/FilePreview.tsx
+++ b/src/renderer/components/FilePreview.tsx
@@ -756,9 +756,9 @@ export function FilePreview({ file, onClose, theme, markdownEditMode, setMarkdow
         }
       }
 
-      // Update match count
+      // Update match count - only reset index if it's truly out of bounds and not already 0
       setTotalMatches(allRanges.length);
-      if (allRanges.length > 0 && currentMatchIndex >= allRanges.length) {
+      if (allRanges.length > 0 && currentMatchIndex >= allRanges.length && currentMatchIndex !== 0) {
         setCurrentMatchIndex(0);
       }
 
diff --git a/src/renderer/contexts/ToastContext.tsx b/src/renderer/contexts/ToastContext.tsx
index 800bbd50..450f466e 100644
--- a/src/renderer/contexts/ToastContext.tsx
+++ b/src/renderer/contexts/ToastContext.tsx
@@ -110,9 +110,12 @@ export function ToastProvider({ children, defaultDuration: initialDuration = 20
 
     // Speak toast via TTS if audio feedback is enabled and command is configured
     if (audioEnabled && audioCommand) {
+      console.log('[ToastContext] Triggering TTS with message:', toast.message, 'command:', audioCommand);
       window.maestro.notification.speak(toast.message, audioCommand).catch(err => {
         console.error('[ToastContext] Failed to speak toast:', err);
       });
+    } else {
+      console.log('[ToastContext] TTS skipped - enabled:', audioEnabled, 'command:', audioCommand);
     }
 
     // Show OS notification if enabled