diff --git a/apps/desktop/src/window/DesktopApplicationMenu.test.ts b/apps/desktop/src/window/DesktopApplicationMenu.test.ts
index 612ec441ba99b..9d4e26f64d515 100644
--- a/apps/desktop/src/window/DesktopApplicationMenu.test.ts
+++ b/apps/desktop/src/window/DesktopApplicationMenu.test.ts
@@ -83,7 +83,7 @@ const layerDesktopWindow = (selectedAction: Deferred.Deferred<string>) =>
     createMain: Effect.die("unexpected createMain"),
     ensureMain: Effect.die("unexpected ensureMain"),
     revealOrCreateMain: Effect.die("unexpected revealOrCreateMain"),
-    activate: Effect.void,
+    activate: Deferred.succeed(selectedAction, "activate").pipe(Effect.asVoid),
     createMainIfBackendReady: Effect.void,
     showConnectingSplash: Effect.void,
     handleBackendReady: () => Effect.void,
@@ -205,6 +205,30 @@ describe("DesktopApplicationMenu", () => {
     }),
   );
 
+  it.effect("reopens the main window from File > Open Window on macOS", () =>
+    Effect.gen(function* () {
+      const selectedAction = yield* Deferred.make<string>();
+      const applicationMenuTemplate =
+        yield* Deferred.make<readonly Electron.MenuItemConstructorOptions[]>();
+
+      yield* configureMenu(selectedAction, applicationMenuTemplate, { platform: "darwin" });
+
+      const fileMenu = (yield* Deferred.await(applicationMenuTemplate)).find(
+        (item) => item.label === "File",
+      );
+      if (!Array.isArray(fileMenu?.submenu)) {
+        throw new Error("Expected File menu submenu to be an array.");
+      }
+      const openWindow = fileMenu.submenu.find((item) => item.label === "Open Window");
+      if (typeof openWindow?.click !== "function") {
+        throw new Error("Expected Open Window menu item to have a click handler.");
+      }
+
+      openWindow.click({} as Electron.MenuItem, undefined, {} as KeyboardEvent);
+      assert.equal(yield* Deferred.await(selectedAction), "activate");
+    }),
+  );
+
   it.effect("never binds Cmd/Ctrl+W to closing the window", () =>
     Effect.gen(function* () {
       for (const platform of ["darwin", "linux", "win32"] as const) {
diff --git a/apps/desktop/src/window/DesktopApplicationMenu.ts b/apps/desktop/src/window/DesktopApplicationMenu.ts
index 44d2c234f8358..f2a6b6307e5a2 100644
--- a/apps/desktop/src/window/DesktopApplicationMenu.ts
+++ b/apps/desktop/src/window/DesktopApplicationMenu.ts
@@ -64,6 +64,11 @@ const runMainContentsCommand = Effect.fn("desktop.menu.runMainContentsCommand")(
   yield* desktopWindow.runMainContentsCommand(command);
 });
 
+const activateMainWindow = Effect.gen(function* () {
+  const desktopWindow = yield* DesktopWindow.DesktopWindow;
+  yield* desktopWindow.activate;
+}).pipe(Effect.withSpan("desktop.menu.activateMainWindow"));
+
 const checkForUpdatesFromMenu = Effect.gen(function* () {
   const updates = yield* DesktopUpdates.DesktopUpdates;
   const electronDialog = yield* ElectronDialog.ElectronDialog;
@@ -191,7 +196,12 @@ export const make = Effect.gen(function* () {
         label: "File",
         submenu: [
           ...(environment.platform === "darwin"
-            ? []
+            ? [
+                {
+                  label: "Open Window",
+                  click: () => runMenuEffect("open-window", activateMainWindow),
+                },
+              ]
             : [
                 {
                   label: "Settings...",