diff --git a/mac/VibeTunnel/Core/Services/NotificationService.swift b/mac/VibeTunnel/Core/Services/NotificationService.swift
index e9c0ab33..a91e77be 100644
--- a/mac/VibeTunnel/Core/Services/NotificationService.swift
+++ b/mac/VibeTunnel/Core/Services/NotificationService.swift
@@ -67,6 +67,13 @@ final class NotificationService: NSObject {
     /// Start monitoring server events
     func start() async {
         logger.info("🚀 NotificationService.start() called")
+        
+        // Check if notifications are enabled in config
+        guard configManager.notificationsEnabled else {
+            logger.info("📴 Notifications are disabled in config, skipping SSE connection")
+            return
+        }
+        
         guard serverManager.isRunning else {
             logger.warning("🔴 Server not running, cannot start notification service")
             return
diff --git a/web/src/client/services/push-notification-service.ts b/web/src/client/services/push-notification-service.ts
index 20f34df4..21a2b2e6 100644
--- a/web/src/client/services/push-notification-service.ts
+++ b/web/src/client/services/push-notification-service.ts
@@ -94,6 +94,9 @@ export class PushNotificationService {
       // Monitor permission changes
       this.monitorPermissionChanges();
 
+      // Auto-resubscribe if notifications were previously enabled
+      await this.autoResubscribe();
+
       this.initialized = true;
       logger.log('push notification service initialized');
     } catch (error) {
@@ -159,6 +162,38 @@ export class PushNotificationService {
     });
   }
 
+  /**
+   * Auto-resubscribe if notifications were previously enabled
+   */
+  private async autoResubscribe(): Promise<void> {
+    try {
+      // Load saved preferences
+      const preferences = await this.loadPreferences();
+
+      // Check if notifications were previously enabled
+      if (preferences.enabled) {
+        // Check if we have permission but no subscription
+        const permission = this.getPermission();
+        if (permission === 'granted' && !this.pushSubscription) {
+          logger.log('Auto-resubscribing to push notifications based on saved preferences');
+
+          // Attempt to resubscribe
+          const subscription = await this.subscribe();
+          if (subscription) {
+            logger.log('Successfully auto-resubscribed to push notifications');
+          } else {
+            logger.warn('Failed to auto-resubscribe, user will need to manually enable');
+            // Update preferences to reflect the failed state
+            preferences.enabled = false;
+            await this.savePreferences(preferences);
+          }
+        }
+      }
+    } catch (error) {
+      logger.error('Error during auto-resubscribe:', error);
+    }
+  }
+
   /**
    * Request notification permission from user
    */