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

Please help can't afford a new computer if I throw this one against the wall. 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’. Office 2016 is already Modern Authentication aware so APP passwords are not required.

Microsoft Office 365 Endless Authentication Loop Issue

• Microsoft Outlook 2016 and some recent builds of Outlook 2013 are not affected by this issue.
• We have been experiencing the exact same issue for months now.
• If this box is greyed out or disabled then you need to reset the Windows Credential Manager first.
• We had the issue where Outlook 2016 kept prompting for a password for an Office 365 user whose laptop was connected to their Office 365 account using Windows 10 Pro.
• This is now the 2nd machine that presents the same issue.

You may have to rebuild/restore your outlook folder/files which is a pain. I’d do that one step at a clear Outlook credentials manager 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 FixTechGuide Outlook repair tutorial 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

You can reply to reactivate the question if you decide you want to continue. Let's Fix Outlook and Office365 Sync Issues start by answering a few simple questions to understand the problem. We have been experiencing the exact same issue for months now. I experience the issue myself as well, every once in a while. On the off chance that none of these things solve this issue for you, please contact our support team at