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 recreate Outlook profile step by step 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

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. On the off chance that none of these things solve this issue for you, please contact our fix Outlook after Windows update issues support team at

Loop of 'Sign in to your account'.

Which to me sounds like the issue is service side, not client side. A vast community of Microsoft Office365 users that are working together to support the product and others. 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. In each case the fix has either been one of the above items or a combination of them. There doesn’t appear to be any pattern to the issue occurring or the problem being limited to any specific computer or user.

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 FixTechGuide Outlook repair tutorial 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.
• I am unable to stay signed in to my work account on Teams, Outlook, Office365 for more than 5 minutes.
• 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.
• Today was the first time in about 2 months that I had the issue.
• We too have been seeing this more and more, all W10 on O365, although we use Okta as our MFA.

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.