diff --git a/apps/desktop/package.json b/apps/desktop/package.json
index 0754c0d1c..553d52797 100644
--- a/apps/desktop/package.json
+++ b/apps/desktop/package.json
@@ -15,7 +15,7 @@
   },
   "dependencies": {
     "effect": "catalog:",
-    "electron": "40.6.0",
+    "electron": "40.7.0",
     "electron-updater": "^6.6.2"
   },
   "devDependencies": {
diff --git a/apps/desktop/src/main.ts b/apps/desktop/src/main.ts
index c3dba6016..2556fc3fc 100644
--- a/apps/desktop/src/main.ts
+++ b/apps/desktop/src/main.ts
@@ -14,6 +14,7 @@ import {
   nativeTheme,
   protocol,
   shell,
+  MenuItem,
 } from "electron";
 import type { MenuItemConstructorOptions } from "electron";
 import * as Effect from "effect/Effect";
@@ -277,6 +278,8 @@ let updateCheckInFlight = false;
 let updateDownloadInFlight = false;
 let updaterConfigured = false;
 let updateState: DesktopUpdateState = initialUpdateState();
+const updateStateListeners = new Set<(state: DesktopUpdateState) => void>();
+updateStateListeners.add(() => emitUpdateState());
 
 function resolveUpdaterErrorContext(): DesktopUpdateErrorContext {
   if (updateDownloadInFlight) return "download";
@@ -559,18 +562,77 @@ async function checkForUpdatesFromMenu(): Promise<void> {
   }
 }
 
+const CHECK_FOR_UPDATES_MENU_ITEM_LABEL_DEFAULT = "Check for Updates...";
+const CHECK_FOR_UPDATES_MENU_ITEM_LABEL_CHECKING = "Checking for Updates...";
+const CHECK_FOR_UPDATES_MENU_ITEM_LABEL_IDLE = CHECK_FOR_UPDATES_MENU_ITEM_LABEL_DEFAULT;
+const CHECK_FOR_UPDATES_MENU_ITEM_LABEL_DISABLED = "Updates unavailable";
+const CHECK_FOR_UPDATES_MENU_ITEM_LABEL_DOWNLOADING = "Downloading update...";
+const CHECK_FOR_UPDATES_MENU_ITEM_LABEL_DOWNLOADED = "Update downloaded";
+const CHECK_FOR_UPDATES_MENU_ITEM_LABEL_AVAILABLE = "Update available";
+const CHECK_FOR_UPDATES_MENU_ITEM_LABEL_UP_TO_DATE = "You're up to date!";
+const CHECK_FOR_UPDATES_MENU_ITEM_LABEL_ERROR = "Update check failed";
+function makeCheckForUpdatesMenuItem(): MenuItem {
+  return new MenuItem({
+    label: CHECK_FOR_UPDATES_MENU_ITEM_LABEL_DEFAULT,
+    click: async () => await handleCheckForUpdatesMenuClick(),
+  });
+}
+const checkForUpdatesMenuItemInAppMenu = makeCheckForUpdatesMenuItem();
+const checkForUpdatesMenuItemInHelpMenu = makeCheckForUpdatesMenuItem();
+
+function updateCheckForUpdatesMenuItem(menuItem: MenuItem, state: DesktopUpdateState): void {
+  switch (state.status) {
+    case "checking":
+      menuItem.label = CHECK_FOR_UPDATES_MENU_ITEM_LABEL_CHECKING;
+      menuItem.enabled = false;
+      break;
+    case "available":
+      menuItem.label = CHECK_FOR_UPDATES_MENU_ITEM_LABEL_AVAILABLE;
+      menuItem.enabled = false;
+      break;
+    case "downloading":
+      menuItem.label = CHECK_FOR_UPDATES_MENU_ITEM_LABEL_DOWNLOADING;
+      menuItem.enabled = false;
+      break;
+    case "downloaded":
+      menuItem.label = CHECK_FOR_UPDATES_MENU_ITEM_LABEL_DOWNLOADED;
+      menuItem.enabled = false;
+      break;
+    case "disabled":
+      menuItem.label = CHECK_FOR_UPDATES_MENU_ITEM_LABEL_DISABLED;
+      menuItem.enabled = false;
+      break;
+    case "error":
+      menuItem.label = CHECK_FOR_UPDATES_MENU_ITEM_LABEL_ERROR;
+      menuItem.enabled = false;
+      break;
+    case "up-to-date":
+      menuItem.label = CHECK_FOR_UPDATES_MENU_ITEM_LABEL_UP_TO_DATE;
+      menuItem.enabled = false;
+      break;
+    case "idle":
+      menuItem.label = CHECK_FOR_UPDATES_MENU_ITEM_LABEL_IDLE;
+      menuItem.enabled = true;
+      break;
+  }
+}
+
+updateStateListeners.add((state) => {
+  updateCheckForUpdatesMenuItem(checkForUpdatesMenuItemInAppMenu, state);
+  updateCheckForUpdatesMenuItem(checkForUpdatesMenuItemInHelpMenu, state);
+});
+
+let applicationMenu: Menu | null = null;
+
 function configureApplicationMenu(): void {
-  const template: MenuItemConstructorOptions[] = [];
+  const template: (MenuItemConstructorOptions | MenuItem)[] = [];
 
   if (process.platform === "darwin") {
     template.push({
       label: app.name,
-      submenu: [
+      submenu: Menu.buildFromTemplate([
         { role: "about" },
-        {
-          label: "Check for Updates...",
-          click: () => handleCheckForUpdatesMenuClick(),
-        },
+        checkForUpdatesMenuItemInAppMenu,
         { type: "separator" },
         {
           label: "Settings...",
@@ -585,7 +647,7 @@ function configureApplicationMenu(): void {
         { role: "unhide" },
         { type: "separator" },
         { role: "quit" },
-      ],
+      ]),
     });
   }
 
@@ -625,16 +687,12 @@ function configureApplicationMenu(): void {
     { role: "windowMenu" },
     {
       role: "help",
-      submenu: [
-        {
-          label: "Check for Updates...",
-          click: () => handleCheckForUpdatesMenuClick(),
-        },
-      ],
+      submenu: Menu.buildFromTemplate([checkForUpdatesMenuItemInHelpMenu]),
     },
   );
 
-  Menu.setApplicationMenu(Menu.buildFromTemplate(template));
+  applicationMenu = Menu.buildFromTemplate(template);
+  Menu.setApplicationMenu(applicationMenu);
 }
 
 function resolveResourcePath(fileName: string): string | null {
@@ -727,7 +785,9 @@ function emitUpdateState(): void {
 
 function setUpdateState(patch: Partial<DesktopUpdateState>): void {
   updateState = { ...updateState, ...patch };
-  emitUpdateState();
+  for (const listener of updateStateListeners) {
+    listener(updateState);
+  }
 }
 
 function shouldEnableAutoUpdates(): boolean {
diff --git a/bun.lock b/bun.lock
index b8e36149f..334eaeb79 100644
--- a/bun.lock
+++ b/bun.lock
@@ -17,7 +17,7 @@
       "version": "0.0.10",
       "dependencies": {
         "effect": "catalog:",
-        "electron": "40.6.0",
+        "electron": "40.7.0",
         "electron-updater": "^6.6.2",
       },
       "devDependencies": {
@@ -1012,7 +1012,7 @@
 
     "effect": ["effect@https://pkg.pr.new/Effect-TS/effect-smol/effect@8881a9b", { "dependencies": { "@standard-schema/spec": "^1.1.0", "fast-check": "^4.5.3", "find-my-way-ts": "^0.1.6", "ini": "^6.0.0", "kubernetes-types": "^1.30.0", "msgpackr": "^1.11.8", "multipasta": "^0.2.7", "toml": "^3.0.0", "uuid": "^13.0.0", "yaml": "^2.8.2" } }],
 
-    "electron": ["electron@40.6.0", "", { "dependencies": { "@electron/get": "^2.0.0", "@types/node": "^24.9.0", "extract-zip": "^2.0.1" }, "bin": { "electron": "cli.js" } }, "sha512-ett8W+yOFGDuM0vhJMamYSkrbV3LoaffzJd9GfjI96zRAxyrNqUSKqBpf/WGbQCweDxX2pkUCUfrv4wwKpsFZA=="],
+    "electron": ["electron@40.7.0", "", { "dependencies": { "@electron/get": "^2.0.0", "@types/node": "^24.9.0", "extract-zip": "^2.0.1" }, "bin": { "electron": "cli.js" } }, "sha512-oQe76S/3V1rcb0+i45hAxnCH8udkRZSaHUNwglzNAEKbB94LSJ1qwbFo8+uRc2UsYZgCqSIMRcyX40GyOkD+Xw=="],
 
     "electron-to-chromium": ["electron-to-chromium@1.5.313", "", {}, "sha512-QBMrTWEf00GXZmJyx2lbYD45jpI3TUFnNIzJ5BBc8piGUDwMPa1GV6HJWTZVvY/eiN3fSopl7NRbgGp9sZ9LTA=="],