Does anyone else run into this problem? Whenever I update macOS on my 27-inch iMac, the first boot afterward is a disaster because the Mac somehow logs in before I enter my admin password and tries to open everything that was open before (I never select the checkbox to open previously open items after restarting, but I do have a LOT of login items). As a result, because my keychain is still locked, all sorts of apps and system processes ask for a password that they would normally get from the keychain. So I’m inundated by dialogs asking for my login password, perhaps 20-30 all told, and all sorts of things don’t work.
The only way to recover is to fight off all the dialogs—many just come back repeatedly if I click Cancel—and restart the Mac again. This can take a while, since apps are in a bad state when they can’t access password-protected resources and services, but once I managed to force the Mac to restart, it comes up perfectly the next time.
This has been going on for ages, and I always forget to ask about it because it only happens five or six times a year, but installing macOS 10.14.4 just reminded me of how freaking annoying it is. It’s only on this Mac, and I assume there’s some .plist that’s corrupt, but I haven’t been able to figure out what.