Windows, Outlook - Authentication Prompts

Brass Contributor

Hey Team, 


We have an interesting issue for a user when they try to access their office 365, EXO Mailbox. I don't know if this is a Office 365, EXO or Windows issue. 


Here is the basic issue: When a user goes to sign into his office 365 account (E1) using his licensed (license key) copy of Office - he receives a Modern Auth Prompt, which then stops. and hangs. 


This is an example of what we see: 


modern auth 2.PNG


That's all we see. That is after the user types in his username and password. The Domain is federated, we OKTA as our IDP. 


I spot checked the even viewer and didn't see anything obvious. anything that said Authentication or Authentication Interface, was blank and had no events. 


I am needing some assistance in the best way to troubleshoot this issue, since it could be either a Microsoft Problem or an OKTA Problem. 


The above was recently tried on a brand new computer, with no saved credentials. Also this used to work up until about last month (different computer). But multiple computers, profiles etc have been tried and we have the same issue. 





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