So, we have a few users that log in using the remote web workplace which translates RDP3389 connections via a TS gateway and tunnels them to 443 in a secure connection.
Like I said.. we have a *few* users that do this. Most use a VPN connection.
Today, I had an issue where the users were unable to authenticate. Caused me a little bit of trouble, but eventually I found it to be that that IIS had Windows authentication denied. Changed to allowed, Fixed.