![]() Instead for the update to 12.5.1 and each since then, unfortunately I have confirmed that an inappropriate alias is created near the root level, and causes problems. I also have heard that updating from an account on the startup disk avoids the problems, but so far I have not remembered to try that. It would be nice for there to be a fix, but who would know if it ever got implemented in a future update? I know Apple engineers do not read these forums, but there seems to be no reason why the minor point update should have broken my setup other than some oversight. Anyway, since there have been no replies to this issue, I thought I post this info to help anyone else running into trouble with Monterey 12.6.4 on a Mac with user directory on a non-startup disk. I fixed the problem by going through the painful and hours long process of rolling back to Monterey 12.6.3. So something in the 12.6.4 update broke the keychain for users with home directories not residing on the startup disk. However if I create a new test user and move their home directory to an external drive, upon logging in for the first time, I get errors that the default keychains cannot be created, asked if I want to reset them, and a continual loop of reset/error dialogs. In any case, if I created a test user with directory on startup drive - no problems. I've done some significant troubleshooting of this issue and have concluded that the problem with the Monterey 12.6.4 update and the authentication issues I was having is related to the fact that my user directory does not reside on the startup disk which is an unusual but useful configuration probably only used by a handful of people. You should be able to log in to your User Space as before the upgrade to 12.4. Go to System Preferences / Users & Groups, unlock, and Option-click the user with a User Space relocated off the System Disk, and Choose to set the path to your relocated user space. Reboot your Mac and again log in to the admin account on the System Disk. The solution is while in the admin account on the System Disk, delete the alias. The erroneous alias will have the same name and be in the same place as the legitimate folder, but can be identified because it has the icon of a folder rather than a disk. Volumes/ to reveal file paths suggested for the externally located User Space. The issue can be revealed by booting into an admin account which is located on the System Disk, then using Finder / Go / Go To Folder. It seems on updating macOS inserts an alias in the file path to user spaces located off the System Disk. I think your problem is a manifestation of an issue that has been known since macOS 12.5.1, discussed here:
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