diff --git a/backend/apps/outputs/outputs.py b/backend/apps/outputs/outputs.py
index fa7c445d..c40571b4 100644
--- a/backend/apps/outputs/outputs.py
+++ b/backend/apps/outputs/outputs.py
@@ -497,6 +497,7 @@ def runtime_status_payload(workspace_id: str, instance: int = 1) -> dict:
         "running": rt.running,
         # 'spawned' vs 'serving': ready flips only once the primary port answered the bind poll (and un-flips when the process dies or is frozen).
         "ready": rt.ready,
+        "boot_failed": bool(getattr(rt, "boot_failed", False)),
         # True when the app is served as a built bundle with no dev-server process (ENG-209).
         "serve_static": rt.serve_static,
         "port": rt.port,
diff --git a/backend/apps/outputs/runtime.py b/backend/apps/outputs/runtime.py
index fb84b9cd..5cd042f4 100644
--- a/backend/apps/outputs/runtime.py
+++ b/backend/apps/outputs/runtime.py
@@ -113,6 +113,8 @@ class AppRuntime:
         self.serve_static: bool = False
         # New-mode only: flips True once something is actually listening on frontend_port (we kick off a background poll task in p_start_new_mode). frontend_url returns null until this flips, so the preview pane doesn't try to navigate to an unbound port and show a "Site can't be reached" error mid-npm-install.
         self.p_frontend_ready: bool = False
+        # Set when the bind poll gave up; the status payload carries it so the card can stop spinning honestly.
+        self.boot_failed = False
         # True only while a live bind-poll task owns the global vite boot lock; start() releases it otherwise.
         self.p_boot_lock_handed_off: bool = False
         # True while the process tree is SIGSTOP'd in the idle pool. A frozen vite still holds its port but can't answer it, so frontend_url must stay null while suspended (else the webview loads a dead port = the ERR_FAILED on fast app-switching).
@@ -427,6 +429,8 @@ class AppRuntime:
                     pass
                 await asyncio.sleep(FRONTEND_BIND_POLL_INTERVAL)
             # Timed out; keep the runtime up (Terminal might show useful errors) but surface why the preview never appeared.
+            # boot_failed reaches the CARD: the log line lands in a Terminal most users never open, so the spinner span "Starting preview" forever (Alex's report).
+            self.boot_failed = True
             self.p_broadcast(LogLine(
                 "runtime",
                 f"[runtime] frontend did NOT bind on port {port} after "
diff --git a/backend/main.py b/backend/main.py
index bf613c2d..2dcfdc8b 100644
--- a/backend/main.py
+++ b/backend/main.py
@@ -315,6 +315,7 @@ async def websocket_runtime_logs(websocket: WebSocket, workspace_id: str, instan
                 # The property is the one honest gate (crashed/suspended vite -> None, static -> serve URL); a duplicate running check here nulled every serve-static app's URL, whose card then waited forever on a process that never exists (the "Starting preview" wedge).
                 "frontend_url": rt.frontend_url,
                 "is_new_mode": rt.is_new_mode,
+                "boot_failed": bool(getattr(rt, "boot_failed", False)),
             },
         }
 
diff --git a/frontend/src/app/pages/Dashboard/cards/DashboardViewCard.tsx b/frontend/src/app/pages/Dashboard/cards/DashboardViewCard.tsx
index 4d3193c2..3c3e2776 100644
--- a/frontend/src/app/pages/Dashboard/cards/DashboardViewCard.tsx
+++ b/frontend/src/app/pages/Dashboard/cards/DashboardViewCard.tsx
@@ -87,6 +87,21 @@ interface Props {
 }
 
 // The app card's loading state while its runtime spins up. One soft pulse, calm copy, and an honest hint only after 9s, a freshly-imported app installs its deps on first open, which is the slow case worth explaining instead of leaving the user staring at a dead screen.
+const BootFailedBody: React.FC<{ onRetry: () => void }> = ({ onRetry }) => {
+  const c = useClaudeTokens();
+  return (
+    <Box sx={{ width: '100%', height: '100%', display: 'flex', flexDirection: 'column', alignItems: 'center', justifyContent: 'center', gap: 1.25, px: 3, textAlign: 'center' }}>
+      <Typography sx={{ fontSize: '0.875rem', color: c.text.primary }}>Preview didn't start</Typography>
+      <Typography sx={{ fontSize: '0.75rem', color: c.text.muted, maxWidth: 260 }}>
+        The app's dev server never came up. The Terminal tab has the exact error.
+      </Typography>
+      <Box role="button" onClick={onRetry} sx={{ mt: 0.5, px: 1.5, py: 0.5, borderRadius: 1, border: `1px solid ${c.border.medium}`, cursor: 'pointer', fontSize: '0.8rem', color: c.text.primary, '&:hover': { bgcolor: c.bg.elevated } }}>
+        Try again
+      </Box>
+    </Box>
+  );
+};
+
 const BootingBody: React.FC = () => {
   const c = useClaudeTokens();
   const [slow, setSlow] = useState(false);
@@ -1012,7 +1027,7 @@ const DashboardOutputPreview: React.FC<{
   const tokens = useClaudeTokens();
   const dispatch = useAppDispatch();
   const workspaceId = output.workspace_id ?? null;
-  const { frontendUrl, isNewMode, isHydrating } = useRuntimePreviewUrl({
+  const { frontendUrl, isNewMode, isHydrating, bootFailed } = useRuntimePreviewUrl({
     workspaceId,
     enabled: !!workspaceId,
     onLog: onRuntimeLog,
@@ -1111,6 +1126,9 @@ const DashboardOutputPreview: React.FC<{
   }
 
   if (isBooting) {
+    if (bootFailed) {
+      return <BootFailedBody onRetry={() => { const tok = getAuthToken(); void fetch(`${API_BASE}/outputs/workspace/${workspaceId}/runtime/restart?instance=${instance}`, { method: 'POST', headers: tok ? { Authorization: `Bearer ${tok}` } : {} }).catch(() => {}); }} />;
+    }
     return <BootingBody />;
   }
 
diff --git a/frontend/src/shared/hooks/useRuntimePreviewUrl.ts b/frontend/src/shared/hooks/useRuntimePreviewUrl.ts
index 4186ba7e..6b0993ac 100644
--- a/frontend/src/shared/hooks/useRuntimePreviewUrl.ts
+++ b/frontend/src/shared/hooks/useRuntimePreviewUrl.ts
@@ -15,6 +15,8 @@ export interface RuntimePreviewState {
   isNewMode: boolean;
   // True until the runtime:status frame lands; prevents placeholder flash on remount when Vite is up.
   isHydrating: boolean;
+  // The bind poll gave up: the spinner must become an honest failure state, not spin forever.
+  bootFailed: boolean;
 }
 
 export interface RuntimePreviewOptions {
@@ -31,6 +33,7 @@ export function useRuntimePreviewUrl(opts: RuntimePreviewOptions): RuntimePrevie
   const [frontendUrl, setFrontendUrl] = useState<string | null>(null);
   const [isNewMode, setIsNewMode] = useState(false);
   const [isHydrating, setIsHydrating] = useState(true);
+  const [bootFailed, setBootFailed] = useState(false);
   // Pin latest onLog so callback identity changes don't tear down/respawn the runtime.
   const onLogRef = useRef(onLog);
   onLogRef.current = onLog;
@@ -80,6 +83,7 @@ export function useRuntimePreviewUrl(opts: RuntimePreviewOptions): RuntimePrevie
               const fu = msg.data?.frontend_url ?? null;
               setFrontendUrl(fu || null);
               setIsNewMode(!!msg.data?.is_new_mode);
+              setBootFailed(!!msg.data?.boot_failed && !fu);
               setIsHydrating(false);
             } else if (msg.event === 'runtime:log') {
               const stream = msg.data?.stream || 'stdout';
@@ -120,7 +124,7 @@ export function useRuntimePreviewUrl(opts: RuntimePreviewOptions): RuntimePrevie
     };
   }, [workspaceId, enabled, instance]);
 
-  return { frontendUrl, isNewMode, isHydrating };
+  return { frontendUrl, isNewMode, isHydrating, bootFailed };
 }
 
 export interface PickPreviewUrlOptions {