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
    2023-03-07T18:32:44+00:00

    Negative, still seems to be occurring. I've tried disabling syncing for Notes, "Reminders" (Tasks), separately, and together with no change. We realistically can't disable Contacts or Calendar, so if they are somehow involved, we might as well switch to using the Outlook app.

    Every time I think it's resolved, I am about to declare victory, then open the Mail app to send a few outbound test messages and experience the "Cannot Send Mail | An error occurred while delivering this message."

    I even found an old iPhone that was tied to this user's account (granted, it had been off for some time), and found some stale messages stuck in their iOS Mail Outbox. I cleared those out in hopes that maybe this was the needle in the haystack, but I still got an error again this morning, so I doubt it was related.

    I've tried attaching the iPhone with the issue to XCode on a Mac and combing through the logfiles, but it logs so... much... stuff... since I have no idea what I'm looking for, I'm drowning in what I think are 99.99% red herrings.

    Going to consider recommending the user make due for now until the next iOS update or consider switching to iOS Outlook.

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  2. Anonymous
    2023-03-07T18:39:50+00:00

    One of our users is the big boss, they don't like the Outlook app. I don't blame them so that's not an option for us. I've also noticed the two users sometimes get duplicate emails sent from the iPad or iPhone. Have you noticed that?

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  3. Anonymous
    2023-03-07T19:01:46+00:00

    Interestingly, we have the same situation in that it's our VIP who is impacted by this, so, yeah, not thrilled with the prospect of a "forced" change to Outlook as that may not go over well.

    One possibly unique aspect of their mailbox is that it's pretty big and has been around for quite a while, so we're talking something like 80GB and 50,000 calendar items (of which we only sync 6 months), so that's one aspect of this particular user that is a bit of an outlier and may explain why we haven't seen this with anybody else yet.

    I don't think I've seen an instance of duplicates yet, but we did have a couple of wonky instances of emails winding up in some sort of garbled Base64 encoding format, which I've also never seen before, and attribute that behavior to whatever other bug seems to be causing this issue.

    The unfortunate thing is that I can't tell whether it's an Apple Mail issue, ActiveSync issue, or Microsoft 365 issue and I'm sure the finger pointing would be instant. Plus it happens so sporadically, I can't reproduce it often enough to truly capture the issue and draw any conclusions.

    So frustrating.

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  4. Anonymous
    2023-03-08T22:16:08+00:00

    Microsoft said it's Apple, I spoke at length with them and tried everything we could... Trying Apple again. Fourth time...

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  5. Anonymous
    2023-03-08T22:33:13+00:00

    OK, that's helpful as I haven't yet tried opening a case with Apple, but will do the same.

    It has to be Apple because I miraculously found an iPhone 13 Pro with iOS 15 still on it and I cannot reproduce this bug using the same user account, yet can often reproduce it on the 14 Pro with iOS 16.3.1

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