diff --git a/AltServer/AppDelegate.swift b/AltServer/AppDelegate.swift
index 356674bc..cda869a6 100644
--- a/AltServer/AppDelegate.swift
+++ b/AltServer/AppDelegate.swift
@@ -41,6 +41,8 @@ class AppDelegate: NSObject, NSApplicationDelegate {
     
     @IBOutlet private var launchAtLoginMenuItem: NSMenuItem!
     @IBOutlet private var installMailPluginMenuItem: NSMenuItem!
+    @IBOutlet private var installAltStoreMenuItem: NSMenuItem!
+    @IBOutlet private var sideloadAppMenuItem: NSMenuItem!
     
     private weak var authenticationAppleIDTextField: NSTextField?
     private weak var authenticationPasswordTextField: NSSecureTextField?
@@ -67,6 +69,9 @@ class AppDelegate: NSObject, NSApplicationDelegate {
         
         self.appMenu.delegate = self
         
+        self.sideloadAppMenuItem.keyEquivalentModifierMask = .option
+        self.sideloadAppMenuItem.isAlternate = true
+        
         let placeholder = NSLocalizedString("No Connected Devices", comment: "")
         
         self.connectedDevicesMenuController = MenuController<ALTDevice>(menu: self.connectedDevicesMenu, items: [])
@@ -491,6 +496,28 @@ extension AppDelegate: NSMenuDelegate
         // Clearing _jitAppListMenuControllers now prevents action handler from being called.
         // self._jitAppListMenuControllers = []
     }
+    
+    func menu(_ menu: NSMenu, willHighlight item: NSMenuItem?)
+    {
+        guard menu == self.appMenu else { return }
+        
+        // The submenu won't update correctly if the user holds/releases
+        // the Option key while the submenu is visible.
+        // Workaround: temporarily set submenu to nil to dismiss it,
+        // which will then cause the correct submenu to appear.
+        
+        let previousItem: NSMenuItem
+        switch item
+        {
+        case self.sideloadAppMenuItem: previousItem = self.installAltStoreMenuItem
+        case self.installAltStoreMenuItem: previousItem = self.sideloadAppMenuItem
+        default: return
+        }
+
+        let submenu = previousItem.submenu
+        previousItem.submenu = nil
+        previousItem.submenu = submenu
+    }
 }
 
 extension AppDelegate: NSTextFieldDelegate
diff --git a/AltServer/Base.lproj/Main.storyboard b/AltServer/Base.lproj/Main.storyboard
index 1c85367a..0916dd2f 100644
--- a/AltServer/Base.lproj/Main.storyboard
+++ b/AltServer/Base.lproj/Main.storyboard
@@ -1,8 +1,8 @@
 <?xml version="1.0" encoding="UTF-8"?>
-<document type="com.apple.InterfaceBuilder3.Cocoa.Storyboard.XIB" version="3.0" toolsVersion="18122" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
+<document type="com.apple.InterfaceBuilder3.Cocoa.Storyboard.XIB" version="3.0" toolsVersion="19162" targetRuntime="MacOSX.Cocoa" propertyAccessControl="none" useAutolayout="YES">
     <dependencies>
         <deployment identifier="macosx"/>
-        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="18122"/>
+        <plugIn identifier="com.apple.InterfaceBuilder.CocoaPlugin" version="19162"/>
         <capability name="documents saved in the Xcode 8 format" minToolsVersion="8.0"/>
     </dependencies>
     <scenes>
@@ -63,8 +63,10 @@
                         <outlet property="authenticationPasswordTextField" destination="9rp-Vx-rvB" id="ZoC-DI-jzQ"/>
                         <outlet property="connectedDevicesMenu" destination="KJ9-WY-pW1" id="Mcv-64-iFU"/>
                         <outlet property="enableJITMenu" destination="la4-Sa-L3C" id="YrW-hR-uA7"/>
+                        <outlet property="installAltStoreMenuItem" destination="MJ8-Lt-SSV" id="KYp-c5-8Ru"/>
                         <outlet property="installMailPluginMenuItem" destination="3CM-gV-X2G" id="lio-ha-z0S"/>
                         <outlet property="launchAtLoginMenuItem" destination="IyR-FQ-upe" id="Fxn-EP-hwH"/>
+                        <outlet property="sideloadAppMenuItem" destination="x0e-zI-0A2" id="GJo-FY-1GO"/>
                         <outlet property="sideloadIPAConnectedDevicesMenu" destination="IuI-bV-fTY" id="QQw-St-HfG"/>
                     </connections>
                 </customObject>