A secure remote assistance session between computers that are behind firewalls and/or NAT devices is provided by an arrangement that uses a terminal services (“TS”) gateway to enable utilization of a remote desktop protocol (“RDP”) connection by a terminal services client in a reverse direction to that used in a conventional terminal services session. The connection is made via a regular TS gateway protocol mechanism by which the TS client behind a firewall establishes a connection to the remote server that is typically behind a firewall that protects a corporate network. The server then functions as the terminal services client to tunnel RDP data through the established TS gateway connection through the NAT firewall to a client. Thus, the server and client reverse roles after the TS gateway connection is made to thereby enable remote viewing of the graphical user interface that is displayed by the client in support of the remote assistance session.