I experience the issue myself as well, every once in a while. Tried CC cleaner to clean up registry and everything -- also keep in mind this Troubleshoot Office 365 Sync and Login Issues is a fairly recent reinstall of windows. I am unable to stay signed in to my work account on Teams, Outlook, Office365 for more than 5 minutes.

Outlook credential prompt loop

In the instances that this occurs the effected user is not new to MFA but has been running it for at least months. The problem appears to randomly affect users (I’ve had it affect myself once too), and the only solution appears to one of (or a combination of) the options in the OP. Out of 140 staff the problem seems to occur once every 2-3 weeks on average. In this case are you saying that there is a password prompt for the users credentials? Clear the Windows Credential manager or recreate the users Outlook profile. In fact if you just turned on MFA and you were not using MFA before you usually end up having to rebuild Fix Outlook and Office365 Sync Issues the profile and clearing the credential manager.

Loop of 'Sign in to your account'.

I had this exact issue on another machine, that after 2.5 hours on the phone with MS support (via Zoom), the solution was to uninstall MS Office 365 and reinstall it. Yeap, you describe it exactly and unfortunately we still don’t have an answer. Closed the window without entering anything and Outlook returned to ‘Connected to Exchange’. I created a new Outlook profile, and then the old one started working. I wonder if the compuer cached a new logon token or something that the old Outlook profile could use. Also, during the new profile creation, I was only prompted for a password and not for MFA.

Resetting the Windows Credential Manager:

If you are saying that they are getting multiple MFA prompts then this is an out of sync issue with the wrong code being used. We’ve got a support case opened with Microsoft on this one but it’s been online Outlook email repair utility open for about 3 months. Unfortunately when the problem occurs they’ve asked us to ring straight away but of course you can never get them instantly (we’ve just been given someone’s direct number now). To make a long story short we’ve since been asked to collect Outlook logs and install Fiddler to capture additional logging. Initially, this account didn't have MFA turned on, and I was able to log in.

• Unfortunately when the problem occurs they’ve asked us to ring straight away but of course you can never get them instantly (we’ve just been given someone’s direct number now).
• This is now the 2nd machine that presents the same issue.
• There doesn’t appear to be any pattern to the issue occurring or the problem being limited to any specific computer or user.
• I disabled the Zoom and Adobe PDF plugins and it stopped prompting me immediately.
• On the main machine where I have been using the suite, now my account is deactivated and if I try to authenticate, it looks like it works but then get the "Fix", "Authenticate", "Activate" or "Resolve" buttons, all of which do nothing.
• I’d do that one step at a time, forgoing the restore of the cached files.

Changing Outlook Security Settings:

If this box is greyed out or disabled then you need to reset the Windows Credential Manager first. @Microsoft, given the level of attention the community has given this issue, I hope you come up with an update soon. We have been experiencing the exact same issue for months now.