Microsoft Enterprise Exchange Problems on iOS 16

Anonymous
2022-10-19T18:56:28+00:00

Since the update to iOS16 and the change to modern authentication, I cannot get my business Exchange account to work properly on the native iOS Mail app for any iPhone or iPad device.

This problem has persisted since iOS16.0 through 16.0.3 and even the forthcoming iOS 16.1 RC. Push mail, or Fetch mail, no longer works. And when in the Mail app for the iOS device, it either gets stuck on "Checking for Mail" or it eventually fails with an error saying “Cannot Get Mail: The connection to the server failed”. It randomly will start fetching mail again, though not through Push or Fetch, only to get stuck at random intervals with "Cannot Get Mail: The connection to the server failed."

I've tried deleting and re-adding the account, resetting all settings on the devices, and even reinstalling iOS 16 fresh and re-adding the accounts. All to no avail. We've checked the Azure AD for error messages during these failures, and we cannot find any errors.

Absent an iOS 16 bug that may or may not be addressed, is there anything I am missing to fix this? I do not want to use the Outlook app, because I manage multiple accounts through the Mail app and do not want to be using multiple apps just to manage mail.

Outlook | Outlook for mobile | Outlook for iOS | For home

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  1. Anonymous
    2023-03-08T23:09:41+00:00

    It's only been an issue since iOS 16 came out for us.

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  2. Anonymous
    2023-03-09T20:38:22+00:00

    Did you connect with Apple? They took logs from my phone and the senior tech passed them on to engineering. More people would help!

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  3. Anonymous
    2023-03-14T14:11:44+00:00

    Apple asked me to reinstall iOS 16.3.1 from scratch and try recreating the issue, so I'll work on that today and (likely) reopen the ticket when I can get it to happen again.

    Obviously this wouldn't really be an ideal situation as it would require manually matching all settings, apps, and data from a new device to the old device, but I'm willing to play along for testing.

    I suggested that perhaps they'd want to collect logs from the problematic device, but they weren't interested UNTIL I first tried wiping it and reinstalling iOS 16.3.1 from scratch.

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  4. Anonymous
    2023-03-14T14:20:41+00:00

    Yuk, I'm in the log collection part with them now...

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  5. Anonymous
    2023-03-22T13:49:52+00:00

    For better or for worse, since setting up a brand new (not restoring from an iCloud or local backup ) iPhone with iOS 16.3.1 and only setting up the user Microsoft 365 Mail profile (I didn't even login to their iCloud account), I have been unable to reproduce this issue over the last ~5 days on either the new "test" iPhone OR, most interestingly, on the formerly problematic iPhone 14 Pro with iOS 16.3.1.

    In other words, either the process of setting up a brand new Mail profile (only) on a brand new device "did something" to fix this issue for us or Microsoft "did something" over the last ~5 days on the ActiveSync/Microsoft 365 side to fix this issue, or I've just been super lucky and haven't been able to reproduce it.

    DustinOKC - If you've got a spare iPhone with iOS 16.3.1 you can wipe, is it worth trying the same on your side? Have you noticed any decrease in instances of this error over the last ~5 days?

    EDIT minutes after posting:

    As if it could read my post and just to spite me, I just now got another "Cannot Send Mail | An error occurred while delivering this message" on the fully restored/original profile iPhone 14 Pro, though it's been nearly 5 days. This shoots down my hunch that Microsoft (or Apple) "did something" on their end to correct this. I still have yet to reproduce this issue on the nearly black/stock iPhone with only the Microsoft 365 Mail profile, so am unable to yet get any further with Apple.

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