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  • Kai Bonney
  • 1141493
  • Issues
  • #1

Closed
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Created Nov 30, 2025 by Kai Bonney@kaibonney72296Maintainer

Resolve Office 365 Authentication Loop Issues Expert Q&A

Content

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

Please help can't afford a new computer if I throw this one against the wall. Yeap, you describe it exactly and unfortunately we still don’t have an answer. Closed the window without entering anything and Outlook returned to ‘Connected to Exchange’. Office 2016 is already Modern Authentication aware so APP passwords are not required.

Microsoft Office 365 Endless Authentication Loop Issue

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.Checking the Account in Word showed the correct authentication and subscription.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.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.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.

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 Outlook Not Sending or Receiving Email 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 connection status shows disconnected 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 Outlook Login Issues Troubleshooting 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.

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