diff --git a/Tautulli.py b/Tautulli.py
index c7faad29..53514f96 100755
--- a/Tautulli.py
+++ b/Tautulli.py
@@ -251,8 +251,6 @@ def main():
     elif common.PLATFORM == 'Darwin':
         macos.set_startup()
 
-    logger.info("Tautulli is ready!")
-
     # Open webbrowser
     if plexpy.CONFIG.LAUNCH_BROWSER and not args.nolaunch and not plexpy.DEV:
         plexpy.launch_browser(plexpy.CONFIG.HTTP_HOST, plexpy.HTTP_PORT,
@@ -269,6 +267,8 @@ def main():
 
 
 def wait():
+    logger.info("Tautulli is ready!")
+
     # Wait endlessly for a signal to happen
     while True:
         if not plexpy.SIGNAL:
diff --git a/plexpy/macos.py b/plexpy/macos.py
index 98a51903..0f657d9e 100644
--- a/plexpy/macos.py
+++ b/plexpy/macos.py
@@ -51,8 +51,8 @@ class MacOSSystemTray(object):
             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.menu.insert(5, rumps.MenuItem('Update', callback=self.tray_update))
+        self.menu[2].state = plexpy.CONFIG.LAUNCH_STARTUP
 
         self.tray_icon = rumps.App(common.PRODUCT, icon=self.icon, menu=self.menu, quit_button=None)