Your question is RDP Fails After Reboot. Take a moment with it on the right.
Talk me through your thinking if you like. When you're confident, submit your answer and I'll grade it like a real screen (7/10 or better passes).
You have just added a route in Server 2008 to allow RDP sessions from inbound traffic. You have tested it and it works. You then install security updates and reboot, and now cannot RDP to the server. What would you check?