I've been experiencing an issue with several M365 tenants where users with iPhones who use the Apple Mail client are constantly being prompted to authenticate their accounts throughout the day. This is causing frustration as their calendars and mail don't sync properly. I've checked the authentication logs, but nothing stands out as the cause. Has anyone else dealt with this problem, and if so, what solutions worked for you?
5 Answers
Over the weekend, I faced a similar issue and ended up deleting and recreating the Exchange account in the iOS Mail settings, which seemed to fix the issue. It might be that a token expired and needed refreshing for authentication to work correctly.
I've run into this issue as well. It seems like the problem may stem from Apple Mail's reliance on EWS, which is being phased out. That's why some tenants work fine while others struggle. Honestly, the best option right now is to switch to the Outlook app if you’re looking for a smoother experience.
We encountered the same frustration. We sync company contacts using Cirasync, and every now and then, users can't see their contacts across devices because of the ‘Re-enter password’ prompt. It usually resolves itself afterward, but it can be annoying for users.
I’d strongly suggest using the Outlook app. There are various guides out there about this, and I modified some conditional access policies too. Be sure to check which CA rules apply when users log in from their iPhones.
I appreciate the tips! I did recommend using the Outlook app, but some users are resistant since they rely on multiple calendars and want to manage notifications effectively. It’s a bit of a balancing act.
Make sure to check the sign-in logs for any irregularities. It could help in pinpointing the issue. Using device compliance can lead to a smoother authentication experience overall.
Thanks for clarifying! I get the EWS situation, but it’s weird that it’s inconsistent across tenants. I’m still trying to wrap my head around why that happens.