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
    2023-03-07T18:22:27+00:00

    KM we are having the same issue, did you ever get the send issue resolved? It's only happening on two of our users and we've tried EVERYTHING I can think of!

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  3. Anonymous
    2023-02-28T19:57:42+00:00

    We just upgraded an older device to iOS 16.3.1 and began to experience this and instances of sporadic "Cannot Send Mail | An error occurred while delivering this message." Other symptoms include being unable to load various items in the expected formatting and instead see it in a Base64 encoded format, etc.

    We've tried deleting and re-adding the the Microsoft 365 account, forced logouts, password resets, etc. and while modern authentication appears to be working fine, not just one, but TWO brand new iPhone 14 Pros with iOS 16.3.1 exhibit the same symptoms for one particular user.

    Each time I think it's fixed, I'll get a sporadic "Cannot Send Mail | An error occurred while delivering this message."

    I am now going to try disabling Notes syncing to see if that works for us, thanks for the tip.

    EDIT: Upon some testing, disabling Notes did not seem to do the trick for us, so I'm going to start by disabling syncing one by one to see if we can find a correlation. Next is Reminders (Tasks).

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  4. Anonymous
    2023-01-24T18:57:26+00:00

    I'm finding the same issue with refusal to authenticate Exchange on the native iOS 16.3 e-mail app as well. Unable to verify account information is all I keep getting after the MFA.

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  5. Anonymous
    2023-01-15T08:38:31+00:00

    Ever figure out a work around for this?

    Having this issue ever since I updated to 16.2 ios ?

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