diff --git a/src/locales/en/messages.json b/src/locales/en/messages.json
index a735d7bca2..ee14578616 100644
--- a/src/locales/en/messages.json
+++ b/src/locales/en/messages.json
@@ -770,7 +770,10 @@
       }
     }
   },
-  "updateAvailableDesc": {
+  "restartToUpdate": {
+    "message": "Restart To Update"
+  },
+  "restartToUpdateDesc": {
     "message": "Version $VERSION_NUM$ is ready to install. You must restart Bitwarden to complete the installation. Do you want to restart and update now?",
     "placeholders": {
       "version_num": {
@@ -782,10 +785,19 @@
   "updateAvailable": {
     "message": "Update Available"
   },
+  "updateAvailableDesc": {
+    "message": "An update was found. Do you want to download it now?"
+  },
   "update": {
     "message": "Update"
   },
   "later": {
     "message": "Later"
+  },
+  "noUpdatesAvailable": {
+    "message": "No updates are currently available. You are using the latest version."
+  },
+  "updateError": {
+    "message": "Update Error"
   }
 }
diff --git a/src/main/menu.main.ts b/src/main/menu.main.ts
index 9b75c0b343..4828166366 100644
--- a/src/main/menu.main.ts
+++ b/src/main/menu.main.ts
@@ -5,6 +5,7 @@ import {
     dialog,
     ipcMain,
     Menu,
+    MenuItem,
     MenuItemConstructorOptions,
     shell,
 } from 'electron';
@@ -20,6 +21,11 @@ export class MenuMain {
         private i18nService: I18nService, private messagingService: MessagingService) { }
 
     init() {
+        this.updaterMain.updateMenuItem = {
+            label: this.i18nService.t('checkForUpdates'),
+            click: () => this.updaterMain.checkForUpdate(true),
+        };
+
         const template: MenuItemConstructorOptions[] = [
             {
                 label: this.i18nService.t('file'),
@@ -308,10 +314,7 @@ export class MenuMain {
         if (process.platform === 'darwin') {
             const firstMenuPart: MenuItemConstructorOptions[] = [
                 { role: 'about' },
-                {
-                    label: this.i18nService.t('checkForUpdates'),
-                    click: () => this.updaterMain.checkForUpdate(),
-                },
+                this.updaterMain.updateMenuItem,
             ];
 
             template.unshift({
@@ -345,10 +348,7 @@ export class MenuMain {
             template[template.length - 1].submenu =
                 (template[template.length - 1].submenu as MenuItemConstructorOptions[]).concat([
                     { type: 'separator' },
-                    {
-                        label: this.i18nService.t('checkForUpdates'),
-                        click: () => this.updaterMain.checkForUpdate(),
-                    },
+                    this.updaterMain.updateMenuItem,
                     {
                         label: this.i18nService.t('about'),
                         click: () => {
diff --git a/src/main/updater.main.ts b/src/main/updater.main.ts
index e5aed96983..23d4d52a5e 100644
--- a/src/main/updater.main.ts
+++ b/src/main/updater.main.ts
@@ -1,4 +1,7 @@
-import { dialog } from 'electron';
+import {
+    dialog,
+    MenuItemConstructorOptions,
+} from 'electron';
 import { autoUpdater } from 'electron-updater';
 
 import { WindowMain } from './window.main';
@@ -9,30 +12,95 @@ const UpdaterCheckInitalDelay = 5 * 1000; // 5 seconds
 const UpdaterCheckInterval = 12 * 60 * 60 * 1000; // 12 hours
 
 export class UpdaterMain {
+    updateMenuItem: MenuItemConstructorOptions;
+
+    private doingUpdateCheck = false;
+    private doingUpdateCheckWithFeedback = false;
+
     constructor(private windowMain: WindowMain, private i18nService: I18nService) { }
 
     async init() {
         global.setTimeout(async () => await this.checkForUpdate(), UpdaterCheckInitalDelay);
         global.setInterval(async () => await this.checkForUpdate(), UpdaterCheckInterval);
 
+        autoUpdater.on('error', (error) => {
+            if (this.doingUpdateCheckWithFeedback) {
+                dialog.showErrorBox(this.i18nService.t('updateError'),
+                    error == null ? "unknown" : (error.stack || error).toString());
+            }
+
+            this.reset();
+        });
+
         autoUpdater.on('update-downloaded', (info) => {
+            this.updateMenuItem.label = this.i18nService.t('restartToUpdate');
+
             const result = dialog.showMessageBox(this.windowMain.win, {
                 type: 'info',
-                title: this.i18nService.t('updateAvailable'),
-                message: this.i18nService.t('updateAvailable'),
-                detail: this.i18nService.t('updateAvailableDesc', info.version),
-                buttons: [this.i18nService.t('update'), this.i18nService.t('later')],
+                title: this.i18nService.t('restartToUpdate'),
+                message: this.i18nService.t('restartToUpdate'),
+                detail: this.i18nService.t('restartToUpdateDesc', info.version),
+                buttons: [this.i18nService.t('restart'), this.i18nService.t('later')],
                 cancelId: 1,
                 defaultId: 0,
                 noLink: true,
             });
+
             if (result === 0) {
                 autoUpdater.quitAndInstall();
             }
         });
+
+        autoUpdater.on('update-available', () => {
+            if (this.doingUpdateCheckWithFeedback) {
+                const result = dialog.showMessageBox(this.windowMain.win, {
+                    type: 'info',
+                    title: this.i18nService.t('updateAvailable'),
+                    message: this.i18nService.t('updateAvailable'),
+                    detail: this.i18nService.t('updateAvailableDesc'),
+                    buttons: [this.i18nService.t('yes'), this.i18nService.t('no')],
+                    cancelId: 1,
+                    defaultId: 0,
+                    noLink: true,
+                });
+
+                if (result === 0) {
+                    autoUpdater.downloadUpdate();
+                } else {
+                    this.reset();
+                }
+            }
+        });
+
+        autoUpdater.on('update-not-available', () => {
+            if (this.doingUpdateCheckWithFeedback) {
+                dialog.showMessageBox(this.windowMain.win, {
+                    message: this.i18nService.t('noUpdatesAvailable'),
+                });
+            }
+
+            this.reset();
+        });
     }
 
-    async checkForUpdate() {
-        return await autoUpdater.checkForUpdatesAndNotify();
+    async checkForUpdate(withFeedback: boolean = false) {
+        if (this.doingUpdateCheck) {
+            return;
+        }
+
+        this.updateMenuItem.enabled = false;
+        this.doingUpdateCheck = true;
+        this.doingUpdateCheckWithFeedback = withFeedback;
+
+        if (withFeedback) {
+            await autoUpdater.checkForUpdates();
+        } else {
+            await autoUpdater.checkForUpdatesAndNotify();
+        }
+    }
+
+    private reset() {
+        this.updateMenuItem.enabled = true;
+        this.doingUpdateCheck = false;
     }
 }