Windows Server 2008 r2: Updating RDP 6.1 to 7.1

Well, unfortunately no one was able to help and it came time where I had to deal with it so I played with it a little bit more and ultimately found something that seems to work, so I'll post it here in case it helps someone else.

My remote connection was connecting directly to the IP address of my server instead of the name in the trusted SSL certificate. So, when I changed my remote connection settings to connect to the trusted name instead of the IP address it worked fine. My assumption is that when you connect directly to the IP address, the RDP-TCP manager looks for a certificate that matches and if it doesn't find one, then it defaults back to the auto-generated one (and if that doesn't exist, then it re-creates it). So, now when I set it to the 3rd party trusted certificate and then connect using the FQDN of that certificate, it stays put.

So, now the scan passes without any flags and I'm good to go.

In order to have more than 2 users at one time on one Windows Server 2008 server using Remote Desktop Services, you must install the Remote Desktop Services role, and purchase the appropriate licensing.

The behavior you're describing occurs when you have USERACCOUNTA and multiple users try to log on to the server as USERACCOUNTA - by default Remote Desktop on 2008 and later allow for one session/account. This includes the console session, BTW. To get around this you uncheck the "restrict each user to a single session" check box in Remote Desktop Session Host Configuration (instructions from Microsoft here).