diff --git a/apps/desktop/src/window/DesktopWindow.test.ts b/apps/desktop/src/window/DesktopWindow.test.ts
index 497b315ef5225..8d1cfb05ccd29 100644
--- a/apps/desktop/src/window/DesktopWindow.test.ts
+++ b/apps/desktop/src/window/DesktopWindow.test.ts
@@ -9,6 +9,7 @@ import * as Layer from "effect/Layer";
 import * as Logger from "effect/Logger";
 import * as Option from "effect/Option";
 import * as Ref from "effect/Ref";
+import * as SubscriptionRef from "effect/SubscriptionRef";
 import * as Schema from "effect/Schema";
 import * as TestClock from "effect/testing/TestClock";
 
@@ -583,8 +584,8 @@ describe("DesktopWindow", () => {
       }),
   );
 
-  it.effect.each(["before", "after"] as const)(
-    "keeps a closed startup window closed until activation %s backend readiness",
+  it.effect.each(["before", "after", "after a restart of"] as const)(
+    "keeps a closed main window closed until activation %s backend readiness",
     (activation) =>
       Effect.gen(function* () {
         const fake = makeFakeBrowserWindow();
@@ -594,10 +595,14 @@ describe("DesktopWindow", () => {
           const windows = yield* DesktopWindow.DesktopWindow;
           yield* windows.ensureMain;
           fake.windowListeners.get("ready-to-show")?.();
+          if (activation === "after a restart of") {
+            yield* windows.handleBackendReady(new URL("http://127.0.0.1:3773"));
+          }
           fake.isDestroyed.mockReturnValue(true);
           fake.windowListeners.get("closed")?.();
           assert.isTrue(Option.isNone(yield* Ref.get(mainWindow)));
-          if (activation === "after") {
+          if (activation === "after a restart of") yield* windows.handleBackendNotReady;
+          if (activation !== "before") {
             yield* windows.handleBackendReady(new URL("http://127.0.0.1:3773"));
             assert.equal(yield* Ref.get(createCount), 1);
           }
@@ -610,6 +615,76 @@ describe("DesktopWindow", () => {
       }),
   );
 
+  it.effect.each([
+    ["a revealing menu action", { reveal: true }, 2],
+    ["a non-revealing menu action", { reveal: false }, 1],
+  ] as const)(
+    "after %s during a restart, a closed main window follows the backend",
+    ([, options, expectedCreates]) =>
+      Effect.gen(function* () {
+        const fake = makeFakeBrowserWindow();
+        const createCount = yield* Ref.make(0);
+        const mainWindow = yield* Ref.make<Option.Option<Electron.BrowserWindow>>(Option.none());
+        yield* Effect.gen(function* () {
+          const windows = yield* DesktopWindow.DesktopWindow;
+          yield* windows.handleBackendReady(new URL("http://127.0.0.1:3773"));
+          fake.isDestroyed.mockReturnValue(true);
+          fake.windowListeners.get("closed")?.();
+          yield* windows.handleBackendNotReady;
+          yield* windows.dispatchMenuAction("open-settings", options);
+          assert.equal(yield* Ref.get(createCount), 1);
+          fake.isDestroyed.mockReturnValue(false);
+          yield* windows.handleBackendReady(new URL("http://127.0.0.1:3773"));
+          assert.equal(yield* Ref.get(createCount), expectedCreates);
+        }).pipe(Effect.provide(layerTest({ window: fake.window, createCount, mainWindow })));
+      }),
+  );
+
+  it.effect("a Dock click after a revealing menu action during a restart opens the window", () =>
+    Effect.gen(function* () {
+      const fake = makeFakeBrowserWindow();
+      const createCount = yield* Ref.make(0);
+      const mainWindow = yield* Ref.make<Option.Option<Electron.BrowserWindow>>(Option.none());
+      yield* Effect.gen(function* () {
+        const windows = yield* DesktopWindow.DesktopWindow;
+        yield* windows.handleBackendReady(new URL("http://127.0.0.1:3773"));
+        fake.isDestroyed.mockReturnValue(true);
+        fake.windowListeners.get("closed")?.();
+        yield* windows.handleBackendNotReady;
+        yield* windows.dispatchMenuAction("open-settings", { reveal: true });
+        assert.equal(yield* Ref.get(createCount), 1);
+        fake.isDestroyed.mockReturnValue(false);
+        yield* windows.activate;
+        assert.equal(yield* Ref.get(createCount), 2);
+        yield* windows.handleBackendReady(new URL("http://127.0.0.1:3773"));
+        assert.equal(yield* Ref.get(createCount), 2);
+      }).pipe(Effect.provide(layerTest({ window: fake.window, createCount, mainWindow })));
+    }),
+  );
+
+  it.effect("reopens a closed main window when a restart recovers from a startup failure", () =>
+    Effect.gen(function* () {
+      const fake = makeFakeBrowserWindow();
+      const createCount = yield* Ref.make(0);
+      const mainWindow = yield* Ref.make<Option.Option<Electron.BrowserWindow>>(Option.none());
+      yield* Effect.gen(function* () {
+        const windows = yield* DesktopWindow.DesktopWindow;
+        const state = yield* DesktopState.DesktopState;
+        yield* windows.handleBackendReady(new URL("http://127.0.0.1:3773"));
+        fake.windowListeners.get("closed")?.();
+        yield* windows.handleBackendNotReady;
+        yield* SubscriptionRef.set(state.primaryBackendStartup, {
+          _tag: "Failing",
+          reason: "readiness timed out",
+          managedPolicy: false,
+          output: "",
+        });
+        yield* windows.handleBackendReady(new URL("http://127.0.0.1:3773"));
+        assert.equal(yield* Ref.get(createCount), 2);
+      }).pipe(Effect.provide(layerTest({ window: fake.window, createCount, mainWindow })));
+    }),
+  );
+
   it.effect.each(["renderer", "backend"] as const)(
     "reveals the painted boot shell when %s becomes ready first",
     (first) =>
diff --git a/apps/desktop/src/window/DesktopWindow.ts b/apps/desktop/src/window/DesktopWindow.ts
index 43404e2d6cfb9..6c5a7f3faaab0 100644
--- a/apps/desktop/src/window/DesktopWindow.ts
+++ b/apps/desktop/src/window/DesktopWindow.ts
@@ -5,6 +5,7 @@ import * as Fiber from "effect/Fiber";
 import * as Layer from "effect/Layer";
 import * as Option from "effect/Option";
 import * as Ref from "effect/Ref";
+import * as SubscriptionRef from "effect/SubscriptionRef";
 import * as Schema from "effect/Schema";
 import * as Semaphore from "effect/Semaphore";
 
@@ -393,8 +394,11 @@ export const make = Effect.gen(function* () {
   const electronApp = yield* ElectronApp.ElectronApp;
   const rendererHistory = yield* DesktopRendererHistory.DesktopRendererHistory;
   const backendReadyRef = yield* Ref.make(false);
-  let backendHasStarted = false;
-  let mainClosedDuringStartup = false;
+  // Backend readiness repeats after every restart, and on macOS the app outlives its last
+  // window, so a window the user closed stays closed until they activate the app.
+  let mainClosed = false;
+  // A revealing request that arrived while the backend was down opens the window once it is back.
+  let revealWhenReady = false;
   const splashWindowRef = yield* Ref.make<Option.Option<Electron.BrowserWindow>>(Option.none());
   const context = yield* Effect.context<DesktopWindowRuntimeServices>();
   const runFork = Effect.runForkWith(context);
@@ -998,7 +1002,7 @@ export const make = Effect.gen(function* () {
     }
 
     window.on("closed", () => {
-      if (!backendHasStarted) mainClosedDuringStartup = true;
+      mainClosed = true;
       clearDevelopmentLoadRetry();
       clearBoundsPersist();
       void runPromise(electronWindow.clearMain(Option.some(window)));
@@ -1010,7 +1014,8 @@ export const make = Effect.gen(function* () {
   const createMain = Effect.gen(function* () {
     const window = yield* createWindow();
     if (Option.isSome(window)) {
-      mainClosedDuringStartup = false;
+      mainClosed = false;
+      revealWhenReady = false;
       yield* logWindowInfo("main window created");
     }
     return window;
@@ -1106,7 +1111,10 @@ export const make = Effect.gen(function* () {
   ) {
     if (yield* Ref.get(desktopState.quitting)) return;
     const existingWindow = yield* reveal ? focusedMainWindow : electronWindow.main;
-    if (Option.isNone(existingWindow) && (!reveal || (yield* waitingForBackend))) return;
+    if (Option.isNone(existingWindow) && (!reveal || (yield* waitingForBackend))) {
+      if (reveal) revealWhenReady = true;
+      return;
+    }
     const window = Option.isSome(existingWindow) ? existingWindow : yield* ensureMain;
     if (Option.isNone(window) || window.value.isDestroyed()) return;
     const targetWindow = window.value;
@@ -1141,7 +1149,7 @@ export const make = Effect.gen(function* () {
         yield* revealMain(existingWindow.value);
         return;
       }
-      if (mainClosedDuringStartup) {
+      if (mainClosed) {
         yield* ensureMain;
         return;
       }
@@ -1158,10 +1166,12 @@ export const make = Effect.gen(function* () {
     createMainIfBackendReady,
     showConnectingSplash,
     handleBackendReady: Effect.fn("desktop.window.handleBackendReady")(function* (httpBaseUrl) {
-      backendHasStarted = true;
       yield* Ref.set(backendReadyRef, true);
       yield* logWindowInfo("backend ready", { source: "http", url: httpBaseUrl.href });
-      if (!mainClosedDuringStartup) yield* createMainIfBackendReady;
+      // A startup failure surfaced the recovery window, which closes only into a main window.
+      const recovering =
+        (yield* SubscriptionRef.get(desktopState.primaryBackendStartup))._tag === "Failing";
+      if (!mainClosed || revealWhenReady || recovering) yield* createMainIfBackendReady;
     }),
     handleBackendNotReady: Ref.set(backendReadyRef, false).pipe(
       Effect.withSpan("desktop.window.handleBackendNotReady"),