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

• FYI outlook 2013 requires a registry setting to work with MA.
• 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.

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. Troubleshoot Office 365 Sync and Login Issues 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

Close and open your web browser again and go into repair corrupted OST in Outlook SuiteFiles. You will most likely need to enter your Microsoft 365 credentials again so ensure you tick any box that says remember my credentials but it should now work for all future documents you open and not require your credentials. Upgrade to Microsoft Edge to take advantage of the latest features, security updates, and technical support. I regret that you are experiencing issues with your Microsoft installation.

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 inbox repair tool alternative 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.