diff --git a/client/desktop/app-handlers/updater/auto-updater/index.js b/client/desktop/app-handlers/updater/auto-updater/index.js
index 1d80a336246793..050c81abbb57a3 100644
--- a/client/desktop/app-handlers/updater/auto-updater/index.js
+++ b/client/desktop/app-handlers/updater/auto-updater/index.js
@@ -47,17 +47,23 @@ class AutoUpdater extends Updater {
 			autoUpdater.allowPrerelease = true;
 			autoUpdater.allowDowngrade = false;
 		}
+
+		// Tracks whether an auto-update check was initiated via menu selection.
+		this.isUserRequested = false;
 	}
 
-	ping() {
+	ping( isUserRequested ) {
 		if ( process.env.DEBUG ) {
 			dialogDebug( 'DEBUG is set: skipping auto-update check' );
 			return;
 		}
 		dialogDebug( 'Checking for update' );
 		autoUpdater.checkForUpdates();
+		this.isUserRequested = isUserRequested;
 	}
 
+	// ignore (available), confirm (available), cancel (available)
+	// not available ( do nothing ) - user initiated
 	onAvailable( info ) {
 		log.info( 'New update is available: ', info.version );
 		bumpStat( 'wpcom-desktop-update-check', `${ getStatsString( this.beta ) }-needs-update` );
@@ -66,6 +72,10 @@ class AutoUpdater extends Updater {
 	onNotAvailable() {
 		log.info( 'No update is available' );
 		bumpStat( 'wpcom-desktop-update-check', `${ getStatsString( this.beta ) }-no-update` );
+		if ( this.isUserRequested ) {
+			this.notifyNotAvailable();
+		}
+		this.isUserRequested = false;
 	}
 
 	onDownloaded( info ) {
@@ -93,6 +103,7 @@ class AutoUpdater extends Updater {
 	}
 
 	onCancel() {
+		this.isUserRequested = false;
 		bumpStat( 'wpcom-desktop-update', `${ getStatsString( this.beta ) }-update-cancel` );
 	}
 
diff --git a/client/desktop/app-handlers/updater/index.js b/client/desktop/app-handlers/updater/index.js
index 3b8632863b7f92..062185e6cf4c55 100644
--- a/client/desktop/app-handlers/updater/index.js
+++ b/client/desktop/app-handlers/updater/index.js
@@ -15,19 +15,19 @@ const log = require( 'desktop/lib/logger' )( 'desktop:updater' );
 
 let updater = false;
 
-module.exports = function () {
+function init() {
 	log.info( 'Updater config: ', Config.updater );
 	if ( Config.updater ) {
 		app.on( 'will-finish-launching', function () {
 			const beta = settings.getSetting( 'release-channel' ) === 'beta';
 			log.info( `Update channel: '${ settings.getSetting( 'release-channel' ) }'` );
 			if ( platform.isOSX() || platform.isWindows() || process.env.APPIMAGE ) {
-				log.info( 'Auto Update' );
+				log.info( 'Initializing auto updater...' );
 				updater = new AutoUpdater( {
 					beta,
 				} );
 			} else {
-				log.info( 'Manual Update' );
+				log.info( 'Initializing manual updater...' );
 				updater = new ManualUpdater( {
 					downloadUrl: Config.updater.downloadUrl,
 					apiUrl: Config.updater.apiUrl,
@@ -47,4 +47,13 @@ module.exports = function () {
 	} else {
 		log.info( 'Skipping Update – no configuration' );
 	}
-};
+}
+
+function getUpdater() {
+	return updater;
+}
+
+// !! Syntax: assignment via intermediary module const is
+// necessary to support both unnamed (default) and named exports !!
+const main = ( module.exports = init );
+main.getUpdater = getUpdater;
diff --git a/client/desktop/lib/menu/app-menu.js b/client/desktop/lib/menu/app-menu.js
index d848ccc5bf59f4..28804293c24648 100644
--- a/client/desktop/lib/menu/app-menu.js
+++ b/client/desktop/lib/menu/app-menu.js
@@ -13,6 +13,8 @@ const WindowManager = require( 'desktop/lib/window-manager' );
 const platform = require( 'desktop/lib/platform' );
 const AppQuit = require( 'desktop/lib/app-quit' );
 const debugMenu = require( './debug-menu' );
+const { getUpdater } = require( 'desktop/app-handlers/updater' );
+const log = require( 'desktop/lib/logger' )( 'desktop:menu' );
 
 /**
  * Module variables
@@ -118,6 +120,15 @@ module.exports = function ( app, mainWindow ) {
 				label: 'Show All',
 				role: 'unhide',
 			},
+			{
+				type: 'separator',
+			},
+			{
+				label: 'Check For Updates',
+				click: function () {
+					checkForUpdates();
+				},
+			},
 			{
 				type: 'separator',
 			}
@@ -126,3 +137,13 @@ module.exports = function ( app, mainWindow ) {
 
 	return menuItems;
 };
+
+function checkForUpdates() {
+	log.info( `User clicked 'Check For Updates'` );
+	const updater = getUpdater();
+	if ( updater ) {
+		updater.ping( true );
+	} else {
+		log.error( 'Updater not set' );
+	}
+}
diff --git a/client/desktop/lib/updater/index.js b/client/desktop/lib/updater/index.js
index 2a67407b177ba9..f228b667fb4376 100644
--- a/client/desktop/lib/updater/index.js
+++ b/client/desktop/lib/updater/index.js
@@ -75,6 +75,17 @@ class Updater extends EventEmitter {
 		}
 	}
 
+	notifyNotAvailable() {
+		const mainWindow = BrowserWindow.getFocusedWindow();
+
+		const notAvailableDialogOptions = {
+			buttons: [ 'OK' ],
+			message: 'There are currently no updates available.',
+		};
+
+		dialog.showMessageBox( mainWindow, notAvailableDialogOptions );
+	}
+
 	setVersion( version ) {
 		this._version = version;
 	}