I have Outlook 365 installed on Windows 11 Pro. Automatic updates are turned on. There is zero chance that Outlook is corrupt. Reinstalling Outlook 365 is out of the question. This PC runs 24/7 and Outlook 365 is configured to get email from 15 different email accounts every 3 minutes. 6 email accounts are from a private hosting company, 6 email accounts are @gmail.com, and 3 are hosted by MS (@live.com or @hotmail.com).
For no apparent reason, one or more of the Microsoft hosted email's login (live or hotmail) will be rejected by the server. Initially, I did the obvious thing thinking that somehow the wrong password was getting sent and manually entered it. I quickly found that wasn't the issue. In an attempt to rule out some kind of online security issue with MS servers, I went online and created an APP Password for all of these MS accounts. This had zero effect on the failure frequency. Sometimes all accounts work for a day, then one will start failing at the password, then that one will start working and another might fail for a few days. Just maddening.
On suspicion that I was being limited by MS servers for checking email too often, I broke the offending email accounts to a different send/receive group in outlook and extended the time from 3 minutes to 15 minutes. I tried several variations of this. The sporadic failure rate continued just the same.
These failures on MS accounts started about 6 months ago.
I have zero problems getting mail from the other 12 accounts.
Unless for some reason Microsoft hosted email accounts (@live.com, @hotmail.com, @outlook.com, etc.) are handled differently inside of Outlook 365, this feels like a MS server-side issue.
If Outlook is running as it needs to be for me to get emails in a timely manner, an Outlook popup message raises over top of the application I'm working with every 3 minutes asking for my password for the failed account. My options are to either disable the failing account from the send/receive group, or turn Outlook off. Neither are good.
Is there some kind of extensive Outlook diagnostic report I can generate and share?
***Moved From Outlook / Windows / Classic Outlook for Windows / For business***