diff --git a/apps/code/src/renderer/features/sessions/service/service.test.ts b/apps/code/src/renderer/features/sessions/service/service.test.ts
index a48d2e94d..3337d15c0 100644
--- a/apps/code/src/renderer/features/sessions/service/service.test.ts
+++ b/apps/code/src/renderer/features/sessions/service/service.test.ts
@@ -2649,6 +2649,96 @@ describe("SessionService", () => {
       );
     });
 
+    const mockPreBootFailedSession = (overrides: Partial<AgentSession> = {}) =>
+      mockSessionStoreSetters.getSessionByTaskId.mockReturnValue(
+        createMockSession({
+          isCloud: true,
+          cloudStatus: "failed",
+          status: "disconnected",
+          ...overrides,
+        }),
+      );
+
+    it("refuses to resume when the previous run failed before the agent booted", async () => {
+      const service = getSessionService();
+      mockPreBootFailedSession({
+        cloudErrorMessage: "Sandbox could not be provisioned",
+      });
+
+      await expect(service.sendPrompt("task-123", "retry?")).rejects.toThrow(
+        "Sandbox could not be provisioned",
+      );
+      expect(mockAuthenticatedClient.runTaskInCloud).not.toHaveBeenCalled();
+    });
+
+    it("falls back to a generic message when the failed run has no error", async () => {
+      const service = getSessionService();
+      mockPreBootFailedSession();
+
+      await expect(service.sendPrompt("task-123", "retry?")).rejects.toThrow(
+        /Cloud run couldn't start/,
+      );
+      expect(mockAuthenticatedClient.runTaskInCloud).not.toHaveBeenCalled();
+    });
+
+    it("still resumes when a previously running agent failed mid-execution", async () => {
+      const service = getSessionService();
+      mockSessionStoreSetters.getSessionByTaskId.mockReturnValue(
+        createMockSession({
+          isCloud: true,
+          cloudStatus: "failed",
+          status: "connected",
+          cloudBranch: "feature/mid-run",
+        }),
+      );
+      mockAuthenticatedClient.getTaskRun.mockResolvedValue({
+        id: "run-123",
+        task: "task-123",
+        team: 123,
+        branch: "feature/mid-run",
+        runtime_adapter: "claude",
+        model: "claude-sonnet-4-20250514",
+        reasoning_effort: null,
+        environment: "cloud",
+        status: "failed",
+        log_url: "https://example.com/logs/run-123",
+        error_message: "agent crashed",
+        output: {},
+        state: {},
+        created_at: "2026-04-14T00:00:00Z",
+        updated_at: "2026-04-14T00:00:00Z",
+        completed_at: "2026-04-14T00:05:00Z",
+      });
+      mockAuthenticatedClient.getTask.mockResolvedValue(createMockTask());
+      mockAuthenticatedClient.runTaskInCloud.mockResolvedValue(
+        createMockTask({
+          latest_run: {
+            id: "run-456",
+            task: "task-123",
+            team: 123,
+            branch: "feature/mid-run",
+            runtime_adapter: "claude",
+            model: "claude-sonnet-4-20250514",
+            reasoning_effort: null,
+            environment: "cloud",
+            status: "queued",
+            log_url: "https://example.com/logs/run-456",
+            error_message: null,
+            output: {},
+            state: {},
+            created_at: "2026-04-14T00:06:00Z",
+            updated_at: "2026-04-14T00:06:00Z",
+            completed_at: null,
+          },
+        }),
+      );
+
+      const result = await service.sendPrompt("task-123", "try again");
+
+      expect(result.stopReason).toBe("queued");
+      expect(mockAuthenticatedClient.runTaskInCloud).toHaveBeenCalledTimes(1);
+    });
+
     it("attempts automatic recovery on fatal error", async () => {
       const service = getSessionService();
       const mockSession = createMockSession({
diff --git a/apps/code/src/renderer/features/sessions/service/service.ts b/apps/code/src/renderer/features/sessions/service/service.ts
index 4a8953a9a..8a42c9ff7 100644
--- a/apps/code/src/renderer/features/sessions/service/service.ts
+++ b/apps/code/src/renderer/features/sessions/service/service.ts
@@ -1660,6 +1660,15 @@ export class SessionService {
     }
 
     if (isTerminalStatus(session.cloudStatus)) {
+      // If the agent never booted (no `run_started`), resuming spins another
+      // sandbox that hits the same provisioning failure — surface the error
+      // instead of looping.
+      if (session.cloudStatus === "failed" && session.status !== "connected") {
+        throw new Error(
+          session.cloudErrorMessage ??
+            "Cloud run couldn't start. Check that GitHub is connected for this project, then try again.",
+        );
+      }
       return this.resumeCloudRun(session, prompt);
     }
 
diff --git a/apps/code/src/renderer/features/task-detail/components/TaskInput.tsx b/apps/code/src/renderer/features/task-detail/components/TaskInput.tsx
index 1590b396a..ab2fa468a 100644
--- a/apps/code/src/renderer/features/task-detail/components/TaskInput.tsx
+++ b/apps/code/src/renderer/features/task-detail/components/TaskInput.tsx
@@ -76,6 +76,7 @@ export function TaskInput({
     trpcReact.folders.getMostRecentlyAccessedRepository.queryOptions(),
   );
   const {
+    lastUsedLocalWorkspaceMode,
     setLastUsedLocalWorkspaceMode,
     lastUsedWorkspaceMode,
     setLastUsedWorkspaceMode,
@@ -115,7 +116,6 @@ export function TaskInput({
   );
 
   const [selectedDirectory, setSelectedDirectory] = useState("");
-  const workspaceMode = lastUsedWorkspaceMode || "local";
   const adapter = lastUsedAdapter;
   const prefillRequestKey = initialPromptKey ?? initialPrompt;
 
@@ -167,12 +167,6 @@ export function TaskInput({
     }
   }, [mostRecentRepo?.path, selectedDirectory]);
 
-  const setWorkspaceMode = (mode: WorkspaceMode) => {
-    setLastUsedWorkspaceMode(mode);
-    if (mode !== "cloud") {
-      setLastUsedLocalWorkspaceMode(mode);
-    }
-  };
   const setAdapter = (newAdapter: AgentAdapter) =>
     setLastUsedAdapter(newAdapter);
 
@@ -185,6 +179,20 @@ export function TaskInput({
     refreshRepositories,
     hasGithubIntegration,
   } = useUserRepositoryIntegration();
+
+  // Stay optimistic while the integration list resolves to avoid flicker.
+  const cloudAvailable = isLoadingRepos || hasGithubIntegration;
+  const workspaceMode: WorkspaceMode =
+    !cloudAvailable && lastUsedWorkspaceMode === "cloud"
+      ? lastUsedLocalWorkspaceMode
+      : lastUsedWorkspaceMode || "local";
+
+  const setWorkspaceMode = (mode: WorkspaceMode) => {
+    setLastUsedWorkspaceMode(mode);
+    if (mode !== "cloud") {
+      setLastUsedLocalWorkspaceMode(mode);
+    }
+  };
   const {
     repositories: visibleCloudRepositories,
     isPending: cloudRepositoriesLoading,
@@ -606,6 +614,7 @@ export function TaskInput({
               onChange={setWorkspaceMode}
               selectedCloudEnvironmentId={selectedCloudEnvId}
               onCloudEnvironmentChange={setSelectedCloudEnvId}
+              cloudAvailable={cloudAvailable}
               size="1"
             />
             {workspaceMode === "worktree" && (
diff --git a/apps/code/src/renderer/features/task-detail/components/WorkspaceModeSelect.tsx b/apps/code/src/renderer/features/task-detail/components/WorkspaceModeSelect.tsx
index 08c8c8b77..ed0579027 100644
--- a/apps/code/src/renderer/features/task-detail/components/WorkspaceModeSelect.tsx
+++ b/apps/code/src/renderer/features/task-detail/components/WorkspaceModeSelect.tsx
@@ -36,6 +36,7 @@ interface WorkspaceModeSelectProps {
   overrideModes?: WorkspaceMode[];
   selectedCloudEnvironmentId?: string | null;
   onCloudEnvironmentChange?: (envId: string | null) => void;
+  cloudAvailable?: boolean;
 }
 
 const LOCAL_MODES: {
@@ -67,6 +68,7 @@ export function WorkspaceModeSelect({
   overrideModes,
   selectedCloudEnvironmentId,
   onCloudEnvironmentChange,
+  cloudAvailable = true,
 }: WorkspaceModeSelectProps) {
   const cloudModeEnabled =
     useFeatureFlag("twig-cloud-mode-toggle") || import.meta.env.DEV;
@@ -80,9 +82,9 @@ export function WorkspaceModeSelect({
     openSettings("cloud-environments", "create");
   }, [openSettings]);
 
-  const showCloud = overrideModes
-    ? overrideModes.includes("cloud")
-    : cloudModeEnabled;
+  const showCloud =
+    cloudAvailable &&
+    (overrideModes ? overrideModes.includes("cloud") : cloudModeEnabled);
 
   const localModes = useMemo(
     () =>