A gaming cloud gaming system and a method of initiating a gaming session. One embodiment of the gaming cloud gaming system includes a computing system having: (1) an entry point operable to receive a game session request and generate instructions for establishing a connection between a client and a game server, and (2) a dynamically configurable reverse proxy operable to proxy for the game server and configured to employ the instructions to create a route to a randomly selected port on the game server through which the connection is makeable.