So I had a chance to check it out and it appears as if the installation of Windows is corrupted. I checked some of the core files (termsrv.dll) using a hex editor. They're not matching up with standard versions. It's not a problem with authentication (usernames/FQDN/etc.) The event viewer starts throwing errors regarding RDP as soon as the computer starts. (Not initializing properly.) I've sent him a stock copy of Windows 7 Pro SP1 64 Bit Retail. Might do an "in-place upgrade"/repair or full reformat. Computer is relatively new.