Problem with Exchange account and MFA after Monterey 12.6.4 update

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Problem with Exchange account and MFA after Monterey 12.6.4 update

I've had a terrible time with Mac Mail and Calendar connecting to my school Exchange account after the update to Monterey 12.6.4. I keep getting prompted to enter my login credentials and go through the Duo Mobile authentication process successfully only to be prompted again for the same credentials anywhere from immediately to a few minutes. This basically makes Mac Mail and Calendar useless for this account. As a workaround, I installed Microsoft Outlook desktop app and that seems to work fine. I also have another machine running 12.6.3 without trouble.

I've tried deleting and re-adding the exchange account, restarting and all the usual tricks. For whatever reason it seems like the authentication just doesn't stick. Is anyone else seeing this problem? Something changed that broke for me and I prefer the Mac apps to Outlook. Any suggestions?

Posted on Mar 30, 2023 12:01 AM

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Answer 1

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Selling_England_by_the_Pound Author

Level 1

12 points

Apr 1, 2023 1:07 AM in response to Selling_England_by_the_Pound

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. In any case, if I created a test user with directory on startup drive - no problems. 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. So something in the 12.6.4 update broke the keychain for users with home directories not residing on the startup disk. I fixed the problem by going through the painful and hours long process of rolling back to Monterey 12.6.3. 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 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. It would be nice for there to be a fix, but who would know if it ever got implemented in a future update?

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Answer 2

Tom Ritch

Level 2

284 points

Apr 6, 2023 9:37 AM in response to Selling_England_by_the_Pound

I think your problem is a manifestation of an issue that has been known since macOS 12.5.1, discussed here:

https://discussions.apple.com/thread/254143123

It seems on updating macOS inserts an alias in the file path to user spaces located off the System Disk.

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 ... /Volumes/ to reveal file paths suggested for the externally located User Space. 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.

The solution is while in the admin account on the System Disk, delete the alias. Reboot your Mac and again log in to the admin account on the System Disk. 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. Restart your Mac. You should be able to log in to your User Space as before the upgrade to 12.4.

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Answer 3

Apr 22, 2023 3:25 PM in response to Selling_England_by_the_Pound

Good news to report. I had enough extra time to devote to a possible hosed install of 12.6.5, so I did attempt the upgrade from 12.6.3 to 12.6.5 from an account with a user directory on the startup disk. First, I made sure my main account which has the relocated user directory was logged out. After the upgrade you'll reboot into the account you started the upgrade from. I logged out of that account and into the account with the relocated user directory and all seems well. Hope this thread anyone else experiencing this problem. The reliable solution seems to perform the upgrade from an account with user directory on the startup disk.

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Answer 4

Tom Ritch

Level 2

284 points

Apr 9, 2023 2:20 PM in response to Selling_England_by_the_Pound

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. 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. Realizing that essentially the same thing had happened, then fixing it, took about half a day each time.

I understand about not wanting to spend any more time on this problem, and I do not know what you did to roll back to 12.6.3. However, beware; you may still have a problem even if it is not bothering you right now. If the problem was due to an alias being created and incorrectly inserted in the file path as discussed, that alias is probably still there and could surprise you, causing trouble in the future.

Unless you know your cleanup while rolling back to 12.6.3 deleted the alias, I recommend you boot from a user space on the startup disk, check for unwanted aliases, and if present delete them as described. This is quick and easy to do, could confirm the mechanism of your earlier issue, and might prevent future headaches.

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Answer 5

Tom Ritch

Level 2

284 points

Apr 11, 2023 8:40 AM in response to Tom Ritch

On https://www.macintouch.com/post/30244/macos-13-3-trap-for-relocated-home-directory/#more-30244 Lee Mendoza reports the update to 13.3.1 resolved this issue in macOS Ventura. Maybe they also got it right this time in macOS Monterey.

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Answer 6

Apr 8, 2023 12:11 PM in response to Tom Ritch

That is interesting, but I do not think this is the case for my situation as I had successfully and dutifully updated my machine from Monterey 12.6.1 thru 12.6.3 without any trouble at all with the same relocated user directory (and performing the update from that user). Only 12.6.4 broke my setup and this is first time in many years of using this kind of configuration that I ever ran into trouble. I read somewhere that updating from an account that resides on the startup drive may avoid the problem entitrely, but after all the time required to recover from this bug, I don't have the will or time to give it a try. It will be interesting to see if Apple even attempts to fix this bug. I'll be staying with 12.6.3 in the meantime.

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Answer 7

Tom Ritch

Level 2

284 points

Apr 10, 2023 2:00 PM in response to Selling_England_by_the_Pound

I did not test updating directly from my relocated user space.

I did test rebooting into a user space on my startup disk before updating. The update ran smoothly. Afterwards the computer was poised to log in to the user space on the startup disk. I logged in, then logged out and logged in to my relocated user space.

All with no problem.

If anyone tries the update from a relocated user space and has trouble, please let us know. Then try the workaround posted above and let us know how that goes.

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Answer 8

Apr 11, 2023 9:36 AM in response to Tom Ritch

Thanks for the update. Glad to hear there are a few reports of success with the new update. I'll need to wait until the weekend to give it a try and I will got the route of installing from a user with home directory on the startup disk to be safe.

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Answer 9

Apr 10, 2023 12:57 PM in response to Selling_England_by_the_Pound

Anyone willing to try Monterey 12.6.5 to see if Apple fixed the problem with relocated user directories?

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Problem with Exchange account and MFA after Monterey 12.6.4 update

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