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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. To locate and view the registry setting for Anonymous Authentication in the Outlook profile, follow these steps. This issue can occur if the Logon network security setting on the Security tab of the Microsoft Exchange dialog box is set to a value other than Anonymous Authentication. Today was the first time in about 2 months that I had the issue. It happened right before lunch, locked my machine, went out for lunch, came back, and logged in, this time successfully.

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

It requests me to login to my microsoft account.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.

You may have to rebuild/restore your outlook folder/files which is a pain. I’d do that one step at a modern authentication troubleshooting 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

I do NOT have this issue with the other laptop, an iPad, a MacBook Pro and diagnose Office activation conflicts 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 reset cached Exchange mode 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.