Using classic Outlook for Windows in business environments
I have been having this problem on three laptops, two Dells and an HP, all three running Windows 11 Pro or Home with older versions of Outlook and Office. They all started doing this recently. I get a pop-up, I put in my password, it pops up again, I close it out, then Outlook says it needs a password on the bottom right, I click on that, the pop-up comes again, I put in my password again, this time, Outlook connect, but I cannot close out the pop-up - I have to just move it out of sight or else it will disconnect again. Every once in a while, I will see that it is "Trying to Connect..." and will do the whole thing over again.
Like someone else said, I had this problem several years ago where it kept asking for my password and I think I was basically locked out for some time. I think it happened after an update. I did get an update recently on my main computer.
This time I have figured out a work-around, but it is painful and I really need Outlook to stay online. Last time, it resolved itself after several weeks. I am sure it is a Microsoft thing.