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Add Resolve Office 365 Authentication Loop Issues Expert Q&A

Ben Huot 2026-01-12 12:42:17 -05:00
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Content<br>
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
I cannot find the phone number again to contact MS Office support (eventually they were helpful, but only after insisting they help!), I'm in the Netherlands so if someone has a phone number, I'd love to get it again.Before you access it, back up the registry for restoration in case problems occur.On the off chance that none of these things solve this issue for you, please contact our support team atClear the Windows Credential manager or recreate the users Outlook profile.The connection to Microsoft Exchange is unavailable.We checked with Word that the account was connected–it was and the we opened Outlook and it immediately connected.
When we opened the old, existing profile it didn’t ask for ANY authentication, it just started working. Modifying the Outlook profile by using the "Profiles" registry path is not supported and may cause your Outlook profile to be in an unsupported state. [Microsoft Outlook Email Repair Tool Online](https://gitlab.innive.com/helenegarling) Serious problems might occur if you modify the registry incorrectly. Before you access it, back up the registry for restoration in case problems occur. We are looking at using conditional access policies where a user with a Domain joined PC is not prompted for MFA.
Outlook stuck in an MFA loop
I do NOT have this issue with the other laptop, an iPad, a MacBook Pro and [expert Outlook tips by FixTechGuide](https://git.epochteca.com/maritzamays958/diagnose-office-activation-conflicts9518/-/issues/4) 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
Microsoft Outlook 2016 and some recent builds of Outlook 2013 are not affected by this issue. Those versions have been updated to prevent the problem that is described in the "Symptoms" section. These versions have the Logon network security setting disabled or removed from the Microsoft Exchange email account [fixtechguide mailbox repair Steps](https://gitlab.mpeeo.com:443/harrietpederso) settings. It requests me to login to my microsoft account. I then approve the login with my authenticator app. Then i get rerouted to the login page again to repeat the process.