diff --git a/packages/app/src/app/_layout.tsx b/packages/app/src/app/_layout.tsx
index 00342cbdb..d82627d0a 100644
--- a/packages/app/src/app/_layout.tsx
+++ b/packages/app/src/app/_layout.tsx
@@ -329,6 +329,7 @@ function HostRuntimeBootstrapProvider({ children }: { children: ReactNode }) {
       store,
       daemonStartService,
       shouldStartDaemon: shouldStartBuiltInDaemon,
+      onGateError: (message) => daemonStartService.recordError(message),
     });
   }, []);
 
@@ -355,9 +356,11 @@ function HostRuntimeBootstrapProvider({ children }: { children: ReactNode }) {
   }, [anyOnlineHostServerId, daemonStartError, daemonStartIsRunning, hasGivenUpWaitingForHost]);
 
   const retry = useCallback(() => {
+    const daemonStartService = getDaemonStartService({ store: getHostRuntimeStore() });
     startDaemonIfGateAllows({
-      daemonStartService: getDaemonStartService({ store: getHostRuntimeStore() }),
+      daemonStartService,
       shouldStartDaemon: shouldStartBuiltInDaemon,
+      onGateError: (message) => daemonStartService.recordError(message),
     });
   }, []);
 
diff --git a/packages/app/src/app/host-runtime-bootstrap.test.ts b/packages/app/src/app/host-runtime-bootstrap.test.ts
index d12dd1939..e3968ef37 100644
--- a/packages/app/src/app/host-runtime-bootstrap.test.ts
+++ b/packages/app/src/app/host-runtime-bootstrap.test.ts
@@ -70,6 +70,27 @@ describe("startHostRuntimeBootstrap", () => {
     expect(daemonStartService.start).not.toHaveBeenCalled();
   });
 
+  it("surfaces gate rejection to onGateError without starting the daemon", async () => {
+    const store = createFakeStore();
+    const daemonStartService = createFakeDaemonStartService();
+    const onGateError = vi.fn();
+
+    startHostRuntimeBootstrap({
+      store,
+      daemonStartService,
+      shouldStartDaemon: async () => {
+        throw new Error("settings file unreadable");
+      },
+      onGateError,
+    });
+    await vi.waitFor(() => {
+      expect(onGateError).toHaveBeenCalledTimes(1);
+    });
+
+    expect(daemonStartService.start).not.toHaveBeenCalled();
+    expect(onGateError).toHaveBeenCalledWith(expect.stringContaining("settings file unreadable"));
+  });
+
   it("does not await the daemon-start promise", () => {
     const store = createFakeStore();
     let resolveStart: ((value: { ok: true }) => void) | undefined;
diff --git a/packages/app/src/app/host-runtime-bootstrap.ts b/packages/app/src/app/host-runtime-bootstrap.ts
index f8de3593f..b75cd01fe 100644
--- a/packages/app/src/app/host-runtime-bootstrap.ts
+++ b/packages/app/src/app/host-runtime-bootstrap.ts
@@ -17,6 +17,7 @@ export interface StartHostRuntimeBootstrapInput {
   store: HostRuntimeBootstrapStore;
   daemonStartService: HostRuntimeBootstrapDaemonStartService;
   shouldStartDaemon: HostRuntimeBootstrapStartGate;
+  onGateError?: (message: string) => void;
 }
 
 export function startHostRuntimeBootstrap(input: StartHostRuntimeBootstrapInput): void {
@@ -24,26 +25,35 @@ export function startHostRuntimeBootstrap(input: StartHostRuntimeBootstrapInput)
   startDaemonIfGateAllows({
     daemonStartService: input.daemonStartService,
     shouldStartDaemon: input.shouldStartDaemon,
+    onGateError: input.onGateError,
   });
 }
 
 export function startDaemonIfGateAllows(input: {
   daemonStartService: HostRuntimeBootstrapDaemonStartService;
   shouldStartDaemon: HostRuntimeBootstrapStartGate;
+  onGateError?: (message: string) => void;
 }): void {
-  if (typeof input.shouldStartDaemon === "boolean") {
-    if (input.shouldStartDaemon) {
+  const gate = input.shouldStartDaemon;
+  if (typeof gate === "boolean") {
+    if (gate) {
       void input.daemonStartService.start();
     }
     return;
   }
 
-  void Promise.resolve(input.shouldStartDaemon()).then((shouldStartDaemon) => {
-    if (shouldStartDaemon) {
-      void input.daemonStartService.start();
-    }
-    return;
-  });
+  void Promise.resolve()
+    .then(() => gate())
+    .then((shouldStartDaemon) => {
+      if (shouldStartDaemon) {
+        void input.daemonStartService.start();
+      }
+      return null;
+    })
+    .catch((error) => {
+      const message = error instanceof Error ? error.message : String(error);
+      input.onGateError?.(`Failed to evaluate desktop daemon settings: ${message}`);
+    });
 }
 
 export const WELCOME_ROUTE: Href = "/welcome";
diff --git a/packages/app/src/runtime/daemon-start-service.test.ts b/packages/app/src/runtime/daemon-start-service.test.ts
index fc642b639..b01ccd841 100644
--- a/packages/app/src/runtime/daemon-start-service.test.ts
+++ b/packages/app/src/runtime/daemon-start-service.test.ts
@@ -188,6 +188,21 @@ describe("DaemonStartService", () => {
     expect(service.getLastError()).toBeNull();
   });
 
+  it("recordError surfaces an external error and notifies subscribers", () => {
+    const fake = createFakeStore();
+    const service = new DaemonStartService({
+      store: fake.store,
+      startDesktopDaemon: async () => makeStatus(),
+    });
+    const notifications = vi.fn();
+    service.subscribe(notifications);
+
+    service.recordError("settings file unreadable");
+
+    expect(service.getLastError()).toBe("settings file unreadable");
+    expect(notifications).toHaveBeenCalledTimes(1);
+  });
+
   it("stops notifying after a subscriber unsubscribes", async () => {
     const fake = createFakeStore();
     let notifications = 0;
diff --git a/packages/app/src/runtime/daemon-start-service.ts b/packages/app/src/runtime/daemon-start-service.ts
index b11fbb0b4..e9437931f 100644
--- a/packages/app/src/runtime/daemon-start-service.ts
+++ b/packages/app/src/runtime/daemon-start-service.ts
@@ -53,6 +53,10 @@ export class DaemonStartService {
     return this.lastError;
   }
 
+  recordError(message: string): void {
+    this.setLastError(message);
+  }
+
   isRunning(): boolean {
     return this.inFlightCount > 0;
   }