When a macOS upgrade appears to go well but won’t maintain startup items and other changes, try migration or even reinstalling.
Apple has improved macOS’s upgrade process tremendously over the years. With recent releases, it’s rare something goes pear-shaped and prevents an upgrade from completing. However, you can sometimes wind up in an in-between state, as one reader found. Your accounts migrated with all their data, but on each restart, macOS loses changes to startup items, System Preferences settings, and even app registrations. The startup volume passes all tests with flying colors: safe mode, First Aid in Disk Utility, reinstalling the operating system from macOS Recovery, and the like.
At this stage, you have only two options:
- Use Migration Assistant to essentially “reinstall” your main user or any affected macOS users.
- Erase the drive and perform a fresh migration omitting network and other settings.
- Erase, reinstall macOS, create a new user, migrate apps, and manually copy over your user files.
In all cases, you don’t change any of your files or make any deletions. The problem appears to be in how macOS tracks what it should be consulting at startup.
Read more at MacWorld.com