Why does Microsoft Outlook keep asking for Password

I'm using an on premises Exchange server, these issues only started when that server was updated with latest patches. I'm only seeing the issue with Outlook running on Windows 11 machines, all of which are enterprise edition.

I too have not messed with my settings.

Overnight I built a brand new machine - brand new local login (thought signing in with MS account - as this is forced so heavily these days). Same issue. Was fine for about 2 hours - then suddenly. BAM - enter your password.

I might try a fresh machine with no MS account - just a local user account.

Microsoft, we all know your focus is on Office 365 and SaaS. However, please respect your customers who have paid for the local Outlook client for the great user interface that it provides. You owe your customers a duty of care and a modicum of respect (please) to look into what is causing this at the backend. Clearly changes in the backend mail settings and the way the Outlook client is trying to connect are causing issues with the Outlook local client on people's machines. These issues are not "user error". These issues we are all experiencing with our Outlook local PC client mail interface application have appeared at the same time for all of us. Please assign a small team to look into this and get it resolved for us. It is so frustrating having this issue (still) which is causing the Outlook local client product to not work correctly for all of us collectively!

Totally agree as nothing changes configuration wise the issue is there one week then not the next. No pattern.

Ms are retiring outlook software and want everyone on web outlook Google that.

So in essence it's wrong we have purchased software and it's not working. Still no way of logging a call.

In all honesty I think we are asking the wrong question. I think the question is "...what is wrong with Microsoft's mail servers...".

I use two Outlook and two Hotmail accounts for various purposes, across my MacBook, iPhone, Windows desktop and Surface laptop.

For several days I have been experiencing this really annoying situation of being prompted for passwords frequently, but inconsistently. I sometimes have to enter the password 5 or more times before it is accepted and verified. I can reliably type my passwords.

I have not messed with my settings.

I believe the issue is at the mail server end of things, maybe with corrupted databases or timeouts on security checks.

I believe all the advice Microsoft give to resolve the issue is nonsense as it assumes the issue is with the user/client end.

Microsoft please sort this problem and communicate the real issue. It has happened before and mysteriously gone again after a few weeks. I assume you found the fault in your platforms.

It is a recent update to Windows 11 or Outlook that has caused this (sometime in 2024) - I have an old laptop (Windows 11) that did not have this fault - I started it up and Outlook was fine for over 1 day. Then I let it do Windows updates, and the same issue as everyone here has described suddenly happened. For months now I've just been quitting Outlook and starting it again - it works for 10-20 mins (using the saved password) before it starts asking for my password again.