diff --git a/plexpy/__init__.py b/plexpy/__init__.py
index f81216de..41316a5b 100644
--- a/plexpy/__init__.py
+++ b/plexpy/__init__.py
@@ -141,6 +141,7 @@ PLEX_SERVER_UP = None
 TRACKER = None
 
 WIN_SYS_TRAY_ICON = None
+MAC_SYS_TRAY_ICON = None
 
 SYS_TIMEZONE = None
 SYS_UTC_OFFSET = None
diff --git a/plexpy/config.py b/plexpy/config.py
index 5dc8ecd5..d2947084 100644
--- a/plexpy/config.py
+++ b/plexpy/config.py
@@ -638,7 +638,7 @@ _CONFIG_DEFINITIONS = {
     'JWT_SECRET': (str, 'Advanced', ''),
     'JWT_UPDATE_SECRET': (bool_int, 'Advanced', 0),
     'SYSTEM_ANALYTICS': (int, 'Advanced', 1),
-    'SYS_TRAY': (int, 'General', 1),
+    'SYS_TRAY_ICON': (int, 'General', 1),
 }
 
 _BLACKLIST_KEYS = ['_APITOKEN', '_TOKEN', '_KEY', '_SECRET', '_PASSWORD', '_APIKEY', '_ID', '_HOOK']
diff --git a/plexpy/macos.py b/plexpy/macos.py
index b1fc0dab..e1375bda 100644
--- a/plexpy/macos.py
+++ b/plexpy/macos.py
@@ -35,28 +35,28 @@ else:
 class MacOSSystemTray(object):
     def __init__(self):
         self.image_dir = os.path.join(plexpy.PROG_DIR, 'data/interfaces/', plexpy.CONFIG.INTERFACE, 'images')
+
         if plexpy.UPDATE_AVAILABLE:
             self.icon = os.path.join(self.image_dir, 'logo-circle-update.ico')
-            self.hover_text = common.PRODUCT + ' - Update Available!'
         else:
             self.icon = os.path.join(self.image_dir, 'logo-circle.ico')
-            self.hover_text = common.PRODUCT
 
         self.menu = [
             rumps.MenuItem('Open Tautulli', callback=self.tray_open),
             rumps.MenuItem('Start Tautulli at Login', callback=self.tray_startup),
             rumps.MenuItem('Check for Updates', callback=self.tray_check_update),
-            rumps.MenuItem('Update', callback=self.tray_update),
             rumps.MenuItem('Restart', callback=self.tray_restart),
             rumps.MenuItem('Quit', callback=self.tray_quit)
         ]
+        if not plexpy.FROZEN:
+            self.menu.insert(3, rumps.MenuItem('Update', callback=self.tray_update))
+        self.menu[1].state = plexpy.CONFIG.LAUNCH_STARTUP
 
-        self.tray_icon = None
+        self.tray_icon = rumps.App(common.PRODUCT, icon=self.icon, menu=self.menu, quit_button=None)
 
     def start(self):
         logger.info("Launching MacOS system tray icon.")
         try:
-            self.tray_icon = rumps.App(common.PRODUCT, icon=self.icon, menu=self.menu, quit_button=None)
             self.tray_icon.run()
         except Exception as e:
             logger.error("Unable to launch system tray icon: %s." % e)
@@ -65,8 +65,8 @@ class MacOSSystemTray(object):
         rumps.quit_application()
 
     def update(self, **kwargs):
-        #self.sys_tray_icon.update(**kwargs)
-        pass
+        if 'icon' in kwargs:
+            self.tray_icon.icon = kwargs['icon']
 
     def tray_open(self, tray_icon):
         plexpy.launch_browser(plexpy.CONFIG.HTTP_HOST, plexpy.HTTP_PORT, plexpy.HTTP_ROOT)
@@ -81,9 +81,6 @@ class MacOSSystemTray(object):
     def tray_update(self, tray_icon):
         if plexpy.UPDATE_AVAILABLE:
             plexpy.SIGNAL = 'update'
-        else:
-            hover_text = common.PRODUCT + ' - No Update Available'
-            self.update(hover_text=hover_text)
 
     def tray_restart(self, tray_icon):
         plexpy.SIGNAL = 'restart'
@@ -91,16 +88,22 @@ class MacOSSystemTray(object):
     def tray_quit(self, tray_icon):
         plexpy.SIGNAL = 'shutdown'
 
-    def change_tray_startup_icon(self):
-        if plexpy.CONFIG.LAUNCH_STARTUP:
-            start_icon = os.path.join(self.image_dir, 'check-solid.ico')
+    def change_tray_update_icon(self):
+        if plexpy.UPDATE_AVAILABLE:
+            self.icon = os.path.join(self.image_dir, 'logo-circle-update.ico')
         else:
-            start_icon = None
-        #self.menu_options[2][1] = start_icon
-        #self.update(menu_options=self.menu_options)
+            self.icon = os.path.join(self.image_dir, 'logo-circle.ico')
+        self.update(icon=self.icon)
+
+    def change_tray_startup_icon(self):
+        self.menu[1].state = plexpy.CONFIG.LAUNCH_STARTUP
+        self.tray_icon.menu = self.menu
 
 
 def set_startup():
+    if plexpy.MAC_SYS_TRAY_ICON:
+        plexpy.MAC_SYS_TRAY_ICON.change_tray_startup_icon()
+
     if plexpy.INSTALL_TYPE == 'macos':
         if plexpy.CONFIG.LAUNCH_STARTUP:
             try:
diff --git a/plexpy/versioncheck.py b/plexpy/versioncheck.py
index 72be1796..733e9d41 100644
--- a/plexpy/versioncheck.py
+++ b/plexpy/versioncheck.py
@@ -168,14 +168,9 @@ def check_update(scheduler=False, notify=False):
         plexpy.UPDATE_AVAILABLE = False
 
     if plexpy.WIN_SYS_TRAY_ICON:
-        image_dir = os.path.join(plexpy.PROG_DIR, 'data/interfaces/', plexpy.CONFIG.INTERFACE, 'images')
-        if plexpy.UPDATE_AVAILABLE:
-            icon = os.path.join(image_dir, 'logo-circle-update.ico')
-            hover_text = common.PRODUCT + ' - Update Available!'
-        else:
-            icon = os.path.join(image_dir, 'logo-circle.ico')
-            hover_text = common.PRODUCT + ' - No Update Available'
-        plexpy.WIN_SYS_TRAY_ICON.update(icon=icon, hover_text=hover_text)
+        plexpy.WIN_SYS_TRAY_ICON.change_tray_update_icon()
+    elif plexpy.MAC_SYS_TRAY_ICON:
+        plexpy.MAC_SYS_TRAY_ICON.change_tray_update_icon()
 
 
 def check_github(scheduler=False, notify=False):
diff --git a/plexpy/windows.py b/plexpy/windows.py
index 9c3e8c28..6f588c75 100644
--- a/plexpy/windows.py
+++ b/plexpy/windows.py
@@ -48,23 +48,22 @@ class WindowsSystemTray(object):
         else:
             start_icon = None
 
-        self.menu_options = [
+        self.menu = [
             ['Open Tautulli', None, self.tray_open, 'default'],
             ['', None, 'separator', None],
             ['Start Tautulli at Login', start_icon, self.tray_startup, None],
             ['', None, 'separator', None],
             ['Check for Updates', None, self.tray_check_update, None],
-            ['Update', None, self.tray_update, None],
             ['Restart', None, self.tray_restart, None]
         ]
+        if not plexpy.FROZEN:
+            self.menu.insert(5, ['Update', None, self.tray_update, None])
 
-        self.tray_icon = None
-        self.start()
+        self.tray_icon = SysTrayIcon(self.icon, self.hover_text, self.menu, on_quit=self.tray_quit)
 
     def start(self):
         logger.info("Launching Windows system tray icon.")
         try:
-            self.tray_icon = SysTrayIcon(self.icon, self.hover_text, self.menu_options, on_quit=self.tray_quit)
             self.tray_icon.start()
         except Exception as e:
             logger.error("Unable to launch system tray icon: %s." % e)
@@ -98,13 +97,22 @@ class WindowsSystemTray(object):
     def tray_quit(self, tray_icon):
         plexpy.SIGNAL = 'shutdown'
 
+    def change_tray_update_icon(self):
+        if plexpy.UPDATE_AVAILABLE:
+            self.icon = os.path.join(self.image_dir, 'logo-circle-update.ico')
+            self.hover_text = common.PRODUCT + ' - Update Available!'
+        else:
+            self.icon = os.path.join(self.image_dir, 'logo-circle.ico')
+            self.hover_text = common.PRODUCT + ' - No Update Available'
+        self.update(icon=self.icon, hover_text=self.hover_text)
+
     def change_tray_startup_icon(self):
         if plexpy.CONFIG.LAUNCH_STARTUP:
             start_icon = os.path.join(self.image_dir, 'check-solid.ico')
         else:
             start_icon = None
-        self.menu_options[2][1] = start_icon
-        self.update(menu_options=self.menu_options)
+        self.menu[2][1] = start_icon
+        self.update(menu_options=self.menu)
 
 
 def set_startup():