
KarmanC.85240 (Customer) asked a question.
Hi there, we recently integrated O365 with Okta SSO and for the most part, everything is working as expected.
There is one issue we are facing, we have have admin accounts in the domain and synced to Okta as well. The user is logged into another PC with their admin credentials through RDP, then tries to access the portal. It looks like the Okta authentication is fine but will be stuck in a loop when sending to the Azure Portal. I've checked the assigned username and it matches.
When visiting http://<>/IWA/authenticated.aspx it shows the correct credentials but no sign on logs from Azure.

This can be caused by Windows Server's Loopback Security Check mechanism prevents access to a web application using the FQDN if an attempt to access it:
1.Takes place from the same server that hosts the application, and
2.Has a hostname that does not match the FQDN.
In order to resolve the issue can perform one of the solution provided on this KB : https://support.microsoft.com/en-us/help/926642/error-message-when-you-try-to-access-a-server-locally-by-using-its-fqd