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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 the profile and clearing the 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.

Additional resources

This is now the 2nd machine that presents the same issue. I have a valid MS 365 subscription that includes 5 device licenses. 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 checked my MS account info page, subscription is fine. 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.

Microsoft Office 365 Endless Authentication Loop Issue

Today was the first time in about 2 months that I had the issue.I experience the issue myself as well, every once in a while.In each case the fix has either been one of the above items or a combination of them.I then approve the login with my authenticator app.Outlook must be online or connected to complete this action.So figuring that was the same issue here, I did the same thing.Those versions have been updated to prevent the problem that is described in the "Symptoms" section.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.

You may have to rebuild/restore your outlook folder/files which is a pain. I’d do that one step at a FixTechGuide fix for stuck folders time, forgoing the restore of the cached files. If this box is greyed out or disabled then you need to reset the Windows Credential Manager first. Or, any suggestion on how to fix this issue, even better.

Outlook stuck in an MFA loop

I do NOT have this issue with the other laptop, an iPad, a MacBook Pro and disable faulty add-ins in Outlook tablet. So figuring that was the same issue here, I did the same thing. I'm also getting Error 29, which the MS support rep couldn't explain to me. I even tried disabling my anti -virus while authenticating, that didn't work.

Outlook 365 Password Prompt Issue on Windows Desktop

So not doing anything at all even seems to work. Which to me sounds disable faulty add-ins in Outlook like the issue is service side, not client side. Problem doesn’t just happen on PC’s connected to the internal network, but can happen when a laptop is remote and connected via external wifi or mobile hotspot.