Mail.app not syncing with Exchange (again)

Question

Mail.app not syncing with Exchange (again)

In Fall of 2020 Mail.app stopped pulling in mail from Exchange. There was a long thread about this at the time. The issue seemed to have something to do with Apple and Microsoft not signing certificates properly and the issue resolved after a couple of weeks. Well, it's back. Now changes made in Mail.app to mail in an Exchange account will not register in Exchange. Changes in iOS sync with Exchange, and those changes are synced in Mail.app, but anything I do in Mail.app on any of my devices will not sync with Exchange. Whether this is a certificate thing again or something else I don't know but it's beyond frustrating to have this return.

This began again in Monterey 12.3 and has continued since.

Posted on Apr 17, 2022 6:22 AM

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Answer 1

Apr 18, 2022 8:44 AM in response to Steven Jones3

Hello Steven Jones3,

We would suggest that you try to isolate what is causing the problem by starting the system in safe mode.

Here are the steps from How to use safe mode on your Mac - Apple Support:

1. Turn on or restart your Mac, then immediately press and hold the Shift key as your Mac starts up.

2. Release the key when you see the login window, then log in to your Mac.

3. You might be asked to log in again. On either the first or second login window, you should see ”Safe Boot” in the upper-right corner of the window.

The computer will take longer to start in safe mode, and the screen may have some distorted video as it starts up. This is normal. Once you are logged in, use the system and test to see if the issue continues.

If everything seems to work as expected, go ahead and restart the computer normally and test again. Starting in safe mode forces the computer to run some disk checks similar to First Aid. This can resolve some issues.

Cheers.

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Answer 2

Gena_D

Community Specialist

Apr 18, 2022 9:13 AM in response to Steven Jones3

Thanks for getting back with us about this, Steven Jones3.

Since this behavior was not resolved with the previous article, further assistance may be needed. We want to make sure you reach the right team for help with your Mail issue, so we recommend that you contact Apple Support directly. Depending on your region, you may be able to reach them here: Get Support.

Thank you for participating in the Apple Support Communities and have a wonderful day.

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Answer 3

Apr 18, 2022 8:55 AM in response to srbwanderer

Thanks, but... if only that would do it. This has been an ongoing and intermittent issue not only for me (see https://discussions.apple.com/thread/251942769?page=1 for just one example). None of what you suggested works, and most of the fixes I've seen appear to be only temporary. I can only conjecture that there is an issue with a certificate shared between Apple and Microsoft or an issue with how Mail.app and Exchange handle large mailboxes or possibly individual email messages that somehow cause this behavior.

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Answer 4

Apr 18, 2022 9:47 AM in response to Gena_D

I just got in touch with them and was told they can't help with this.

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Mail.app not syncing with Exchange (again)

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