Fix constant sign-in prompt for Microsoft

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The user could use the Windows mail and calendar apps but Outlook wouldn’t connect and kept prompting for a password.



credential loop in Microsoft 365

But by mistake, I turned on MFA for the admin account, and then when I logged in again, it prompted me to use Microsoft Authenticator. The bad thing is this account was not registered with Microsoft Authenticator, so I couldn't see any codes inbox repair tool alternative in the authenticator. And there were no other login options, and I was stuck in a login loop. 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.

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 Office 365 Sync Errors Fix support team at

credential loop in Microsoft 365

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.

credential loop in Microsoft 365

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 Office 365 Sync Errors Fix better. I do NOT have this issue with the other laptop, an iPad, a MacBook Pro and tablet.

  • If this box is greyed out or disabled then you need to reset the Windows Credential Manager first.
  • I created a new Outlook profile, and then the old one started working.
  • 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.
  • Out of 140 staff the problem seems to occur once every 2-3 weeks on average.
  • But by mistake, I turned on MFA for the admin account, and then when I logged in again, it prompted me to use Microsoft Authenticator.
  • 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.
  • I'm also getting Error 29, which the MS support rep couldn't explain to me.
  • I experience the issue myself as well, every once in a while.
  • I’ve seen this happen when the time and or date is wrong on the machine.


Changing Outlook Security Settings:



Hi, my office 365 account used to work with my desktop apps, I have confirmed with my admin system twice already that I have the appropriate license and everything is enabled but i keep getting stuck in this loop. We are looking at using conditional access policies where a user with a Domain joined PC is not prompted for MFA. Right now we have it set to prompt when a user is not on any of our corporate networks or they are using a mobile device. The 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.
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