Last week I upgraded my 2013 MacBook Pro from Ventura to Sonoma. I have an external bootable SSD, so it needed to be updated too. I decided rather than re-clone it, I’d just apply the Sonoma upgrade to it.
I did that by running the Sonoma installer from the internal drive, rather than booting to the external drive first. This seemed go well, except that it didn’t accept my password on the first boot. Or any other boot, because I couldn’t get past that point.
I’ve seen this before. It was the same deal when I upgraded an external drive from Catalina to Big Sur, while booted into Catalina on my Intel Mac’s Fusion Drive. My notes say that I got it to work on a “2nd attempt”, but no more details. Maybe I just tried the same upgrade again.
Anyway, this time Google said that if you can’t get the Sonoma upgrade to work, you can accept the offer to reboot into macOS Recovery and reset the password. Which I did.
Big mistake. For two reasons: 1) It reset the password on the wrong volume! It reset it on the internal drive (which was perfectly fine), instead of on the external drive, and more importantly 2) reseting the password also wipes out your keychain, Touch ID, iCloud sync, and anything else that is secretive.
But I’m of the opinion that what macOS did is a bug. If I’m having trouble with the password, and it asks me if I want it to restart in macOS Recovery to reset it, I would expect it to restart in macOS Recovery to reset the password on the same volume that I’m already trying the password with.
And, it should tell you which volume you’re recovering. And, and, it should warn you that resetting the password has consequences. I’m still running into things it broke, a week later.
Meanwhile: the ultimate solution for my problem was to do a full ASR clone to the external drive.
Next time, I’ll try booting into the external drive, then apply the macOS update. This is definitely the way to go when macOS gives you the option of updating from System Preferences. I couldn’t do that this time because it would have jumped over Sonoma, to Sequoia.