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 clear Outlook credentials manager 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 FixTechGuide login issue guide the profile and clearing the credential manager.

Loop of 'Sign in to your account'.

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. The repeated issue logging in started after I enabled the modern authentication in the Office 365 administration panel. The user could use the Windows mail and calendar apps but Outlook wouldn’t connect and kept prompting for a password. Checking the Account in Word showed the correct authentication and subscription.

Resetting the Windows Credential Manager:

I have contacted my organization and everything looks alright from their end.. I went as far as getting a new device but it did not cut it. When I try to sign again it will be stuck in sign in loop with the message " Taking you to your organization sign in page" after I have logged in on my company site... When I log in to my account at first from a new device or after a while, it stays signed in and I can work peacefully for about an hour, then it automatically signs me out. Or, any suggestion on how to fix this issue, even guide to Office 365 sign-in errors better. I do NOT have this issue with the other laptop, an iPad, a MacBook Pro and tablet.

• We’ve got a support case opened with Microsoft on this one but it’s been open for about 3 months.
• It would be nice if it distinguished between your password and the app password.
• We have been experiencing the exact same issue for months now.
• Create your account and connect with a world of communities.
• The user had Office 2015 and Office 2016 credentials and Teams credentials that we deleted.
• We too have been seeing this more and more, all W10 on O365, although we use Okta as our MFA.
• Upgrade to Microsoft Edge to take advantage of the latest features, security updates, and technical support.

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.