Microsoft Outlook and macOS Mail problems

[pshufd]

I've had the problem where an Outlook account hooked up to Apple Mail on macOS gives me this message that I need to re-enter the password for the mail account. So I go to enter the password but I get no new emails on the account. The only thing that works is deleting the account and adding it back again and then downloading all of the emails again. I have to do this every couple of months.

I see this in High Sierra as well as Monterey so it's not specific to a macOS version. But I couldn't find a forum for macOS hardware that was generic.

I'm happy that I have a workaround but it would be nice if this didn't regularly break. I don't know if this is a Microsoft or Apple problem or both.

 

[Amazon Rainforest]

This has happened to me too though I cannot say yours is the same problem. What I did to fix this was to log into my Outlook email account directly from a browser and see what it says. Mine said that there was some suspicious activity on my account (there wasn't). I followed the steps laid out by Microsoft to verify everything was OK with my account then all was right again. My problem was due to my use of a VPN.

 

[NoBoMac]

Might need to generate an app specific password in Outlook. Can also try setting up on Mac as Exchange if not already doing that (basically the same when dealing with outlook.com accounts).