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

• 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.
• Checking the Account in Word showed the correct authentication and subscription.
• FYI outlook 2013 requires a registry setting to work with MA.
• These versions have the Logon network security setting disabled or removed from the Microsoft Exchange email account settings.
• I have a valid MS 365 subscription that includes 5 device licenses.
• Have looked all over and people have all sorts of possible solutions, but nothing we found to resolve the issue and get a new issue daily and just keep going through until it eventually works.
• The user had Office 2015 and Office 2016 credentials and Teams credentials that we deleted.

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

The FixTechGuide mailbox repair steps user had Office 2015 and Office 2016 credentials and Teams credentials that we deleted. We checked with Word that the account was connected–it was and the we opened Outlook and it immediately connected. We too have been seeing this more and more, all W10 on O365, although we use Okta as our MFA. Have looked all over and people have all sorts of possible solutions, but nothing we found to resolve the issue and get a new issue daily and just keep going through until it eventually works. I’ve seen this happen when the time and or date is wrong on the machine. It’s not caused by an out of sync MFA prompt as I have personally looked at a number of cases with the user as stepped through it.

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 MFA prompts not working 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