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Also, at the time, that user did not have MFA turned on. 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.

Additional resources

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. I checked my MS account info page, subscription is fine. 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.

Microsoft Office 365 Endless Authentication Loop Issue

We’ve got a support case opened with Microsoft on this one but it’s been open for about 3 months.There doesn’t appear to be any pattern to the issue occurring or the problem being limited to any specific computer or user.We are looking at using conditional access policies where a user with a Domain joined PC is not prompted for MFA.I checked my MS account info page, subscription is fine.When we opened the old, existing profile it didn’t ask for ANY authentication, it just started working.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.The user could use the Windows mail and calendar apps but Outlook wouldn’t connect and kept prompting for a password.

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. By chatting and providing personal info, you understand and agree to our Terms of fix MFA prompts not working Service and Privacy Policy. I disabled the Zoom and Adobe PDF plugins and it stopped prompting me immediately. My client’s Outlook will only continuously ask for the password after MFA is enforced and Office.com has been logged in. It would be nice if it distinguished between your password and the app password.

Outlook stuck in an MFA loop

I do NOT have this issue with the other laptop, an iPad, a MacBook Pro and fix MFA prompts not working 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

So not doing anything at all even seems to work. Which to me sounds FixTechGuide email error solutions like the issue is service side, not client side. 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.