Thanos

@Vero thanks for the swift reply! With your suggestion I understood and fixed the problem in the end: The login list already contained an "Alfred 4" app which was no longer there since the upgrade (moooonths ago). After I did that, the checkbox selection was persisted properly and Alfred 5 could add itself again in the Login Item list. So perhaps it's a good suggestion for Alfred to able to manage that version conflict or warn about what to do manually when it happens. Thanks a lot!

OS: Sonoma 14.1.1 Alfred: 5.1.4 [2195] Things I've tried: - deleting any Alfred directories I've found (e.g. in ~/Library/Application\ Support) - deleting the app - "Clear application cache" from the app itself - Re-"Request for permissions" using the app itself But I can always replicate it: disappointedly manually running alfred from the spotlight or application menu open alfred preferences (via alfred or toolbar) check the "Startup: Launch Alfred at login" button. (even waiting a bit) click "Quit Alfred" restart using 1. and see the option unchecked again On restart Alfred is also not running again. So it's not just the checkbox that's not showing but the start on login functionality is also not as expected. Can I see application logs somewhere?