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
    2023-03-29T01:25:28+00:00

    16.4 did not fix the issue as our Apple engineer claimed it would.

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  2. Anonymous
    2023-03-28T18:40:05+00:00

    This is interesting and may help some others? We don't specifically use InTune, though we do have various conditional access rules, but they generally apply to everybody and we've only really seen this issue with one VIP user.

    I do see that iOS 16.4 appears to be generally available, so I'm definitely going to try that on my replica "problematic" iPhone.

    FWIW, I've still yet to be able to reproduce the issue on a fresh install iOS 16.3.2 iPhone with NOTHING else except the Mail profile, so that does indicate that some other interaction of the apps or settings or iCloud user profile may be involved here. (And this is also the reason I've not been able to get any further with Apple as they won't proceed any further on our open ticket until I can reproduce the issue on the "fresh install" iPhone.)

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  3. Anonymous
    2023-03-27T19:30:30+00:00

    I had a similar experience after setting up my email account on an extra phone for testing a couple months ago then iOS mail on my normal phone started working. I did not tie that together until reading this since I had been changing a lot of things testing. Anyone else using Intune conditional access policies for email? We require intune to mark the phone as compliant with our requirements or email won't work. All the phones are compliant and reporting normally. I have been doing some testing around this the last week but nothing conclusive yet. Early reports of people excluded from the conditional access policy reported email working better.

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  4. Anonymous
    2023-03-22T14:50:29+00:00

    I tried what you suggested, got the error almost immediately. I'm in the process of paying Apple for enterprise engineering support.

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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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