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macOS Mail.app and Outlook

The problem with mail on macOS has been dragging on for a long time. Technical support cannot advise anything, only promising that the problems will be eliminated ... someday, but this is not certain.

The crux of the problem is that by adding an Exchange account to the Mail application, Exchange works correctly from several hours to several days. Then it writes that it cannot connect to the server and that's it. Only deleting the account from the mac and re-configuring it helps.

I decided to switch to Outlook on a 365 subscription. It’s even worse, a minute after the launch, the connection is lost, in the settings the server itself changes to the wrong one. For example, the correct server is https://my.company.com, and the mail works, but spontaneously changes to https://srv-my.company.com and that's it, it doesn't connect until you fix it to the correct one and restart the application. But after launch, it also lives for about a minute and breaks down again.

Everything works fine on Windows, it works fine through the browser, it works fine on the iPhone, and even in the Mail application on iPhone it never broke.

What could be the problem?

MacBook Air (2020 or later)

Posted on Sep 16, 2021 5:42 AM

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Question marked as Top-ranking reply

Posted on Sep 16, 2021 8:24 AM

Because Windows is very forgiving and because iOS is external likely using ActiveSync tech with Microsoft Intune which configures things differently. It's very complex to set things up correctly with 365. This is an Apple Support Community we do not support 365 configuration. You'll need to check with your IT department about the autodiscover changing the server connection. On a properly configured system you would enter your work email and password and it would just magically connect from Outlook. The autodiscover is changing the server connection to one that doesn't work. Something is misconfigured somewhere. In Windows enterprise environments, a Mac typically acts like the canary in a coal mine. The Macs may have problems that Windows do not. But that doesn't mean that things are properly configured. More often than not, fixing the Mac problem results in a better overall system for everyone.



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Question marked as Top-ranking reply

Sep 16, 2021 8:24 AM in response to NickTK

Because Windows is very forgiving and because iOS is external likely using ActiveSync tech with Microsoft Intune which configures things differently. It's very complex to set things up correctly with 365. This is an Apple Support Community we do not support 365 configuration. You'll need to check with your IT department about the autodiscover changing the server connection. On a properly configured system you would enter your work email and password and it would just magically connect from Outlook. The autodiscover is changing the server connection to one that doesn't work. Something is misconfigured somewhere. In Windows enterprise environments, a Mac typically acts like the canary in a coal mine. The Macs may have problems that Windows do not. But that doesn't mean that things are properly configured. More often than not, fixing the Mac problem results in a better overall system for everyone.



macOS Mail.app and Outlook

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