diff --git a/client/src/components/ProjectsSidebar.tsx b/client/src/components/ProjectsSidebar.tsx
index 7e3d10b..b002a12 100644
--- a/client/src/components/ProjectsSidebar.tsx
+++ b/client/src/components/ProjectsSidebar.tsx
@@ -15,6 +15,7 @@ import {
   Wrench,
   RefreshCw,
   ClipboardList,
+  AlertCircle,
 } from 'lucide-react';
 import { useApp } from '../hooks/useApp';
 import { useNotifications } from '../context/NotificationContext';
@@ -38,7 +39,8 @@ export function ProjectsSidebar({
   isCollapsed = false,
   onExpand,
 }: ProjectsSidebarProps) {
-  const { projects, repositories, handleDeleteRepository } = useApp();
+  const { projects, repositories, handleDeleteRepository, loading, error, refreshData } =
+    useApp();
   const { showNotification } = useNotifications();
   const navigate = useNavigate();
   const router = useRouterState();
@@ -386,6 +388,23 @@ export function ProjectsSidebar({
         </div>
       </div>
 
+      {error && !loading && (
+        <div className="mb-3 p-3 rounded-lg bg-red-50 dark:bg-red-900/20 border border-red-200 dark:border-red-800 text-sm text-red-700 dark:text-red-300 flex items-start gap-2">
+          <AlertCircle className="w-4 h-4 shrink-0 mt-0.5" />
+          <div className="flex-1 min-w-0">
+            <p>Couldn't reach the server to load your projects.</p>
+            <button
+              type="button"
+              onClick={() => refreshData()}
+              className="mt-1 inline-flex items-center gap-1 font-medium hover:underline"
+            >
+              <RefreshCw className="w-3 h-3" />
+              Retry
+            </button>
+          </div>
+        </div>
+      )}
+
       <div className="space-y-1 flex-1 overflow-y-auto">
         {projects.map((project) => {
           const projectRepos = projectRepoMap.get(project.id) || [];
diff --git a/client/src/context/AppContext.tsx b/client/src/context/AppContext.tsx
index db49f22..63879e6 100644
--- a/client/src/context/AppContext.tsx
+++ b/client/src/context/AppContext.tsx
@@ -12,29 +12,55 @@ import {
 } from '../api';
 import { AppContext } from './context';
 
+// The client and server start as separate containers with no readiness
+// handshake between them - on a stack restart the client's first request can
+// beat the server to accepting connections. Retry the initial load a few
+// times before surfacing an error, so a normal restart doesn't strand the
+// user on an empty project list.
+const INITIAL_LOAD_MAX_ATTEMPTS = 4;
+const INITIAL_LOAD_RETRY_DELAY_MS = 1000;
+
+const sleep = (ms: number) => new Promise((resolve) => setTimeout(resolve, ms));
+
 export function AppProvider({ children }: { children: ReactNode }) {
   const [projects, setProjects] = useState<Project[]>([]);
   const [repositories, setRepositories] = useState<Repository[]>([]);
   const [loading, setLoading] = useState(true);
   const [error, setError] = useState<string | null>(null);
 
-  const refreshData = async () => {
+  const loadData = async (): Promise<boolean> => {
     try {
-      setLoading(true);
       setError(null);
       const [projectList, repoList] = await Promise.all([getProjects(), getRepositories()]);
       setProjects(projectList);
       setRepositories(repoList);
+      return true;
     } catch (err) {
       setError('Failed to load data');
       console.error('Failed to load data:', err);
-    } finally {
-      setLoading(false);
+      return false;
     }
   };
 
+  const refreshData = async () => {
+    setLoading(true);
+    await loadData();
+    setLoading(false);
+  };
+
   useEffect(() => {
-    refreshData();
+    const loadWithRetry = async () => {
+      setLoading(true);
+      for (let attempt = 1; attempt <= INITIAL_LOAD_MAX_ATTEMPTS; attempt++) {
+        const succeeded = await loadData();
+        if (succeeded) break;
+        if (attempt < INITIAL_LOAD_MAX_ATTEMPTS) {
+          await sleep(INITIAL_LOAD_RETRY_DELAY_MS * attempt);
+        }
+      }
+      setLoading(false);
+    };
+    loadWithRetry();
   }, []);
 
   const handleAddProject = async (name: string, description?: string) => {