diff --git a/frontend/src/pages/Sites/List.tsx b/frontend/src/pages/Sites/List.tsx
index d2c942e7..6b5a9b8b 100644
--- a/frontend/src/pages/Sites/List.tsx
+++ b/frontend/src/pages/Sites/List.tsx
@@ -66,12 +66,13 @@ type ViewType = 'table' | 'grid';
 export default function SiteList() {
   const navigate = useNavigate();
   const toast = useToast();
-  const { toggleGuide, isGuideVisible } = useOnboardingStore();
+  const { toggleGuide, isGuideVisible, showGuide, dismissGuide } = useOnboardingStore();
   const [sites, setSites] = useState<Site[]>([]);
   const [filteredSites, setFilteredSites] = useState<Site[]>([]);
   const [loading, setLoading] = useState(true);
   const [viewType, setViewType] = useState<ViewType>('grid');
   const [showFilters, setShowFilters] = useState(false);
+  const [previousSiteCount, setPreviousSiteCount] = useState<number>(0);
   
   // Site Management Modals
   const [selectedSite, setSelectedSite] = useState<Site | null>(null);
@@ -91,6 +92,19 @@ export default function SiteList() {
     loadSites();
   }, []);
 
+  // Auto-show guide when no sites, auto-hide ONLY when first site is added
+  useEffect(() => {
+    if (sites.length === 0) {
+      // Always show guide when no sites exist
+      showGuide();
+    } else if (previousSiteCount === 0 && sites.length > 0 && isGuideVisible) {
+      // Auto-collapse guide ONLY when transitioning from 0 to 1+ sites
+      dismissGuide();
+    }
+    // Update previous count
+    setPreviousSiteCount(sites.length);
+  }, [sites.length]);
+
   const loadUserPreferences = async () => {
     // User preferences are now loaded from site/account data, not from a separate endpoint
     // This function is kept for backward compatibility but does nothing
@@ -547,8 +561,8 @@ export default function SiteList() {
         </div>
       </div>
       
-      {/* Welcome Guide - Shows when user clicks Add New Website button OR when no sites exist */}
-      {(isGuideVisible || sites.length === 0) && (
+      {/* Welcome Guide - Shows when no sites exist (always) OR when user toggles it (when sites exist) */}
+      {(sites.length === 0 || (sites.length > 0 && isGuideVisible)) && (
         <div className="mb-6">
           <WorkflowGuide 
             onSiteAdded={() => {