Current incarnations of cyber competitions emphasize network attack and defense over information assurance. Capturing or defending network assets represents an end, rather than a means to accomplish a broader mission. In this paper we present a cyber competition paradigm focused on assuring a mission. Consistent with traditional engineering competitions, competitors bring their own designed artifacts to the competition to fulfill their assigned mission. Our competition focuses on assuring orders transmitted across a cloud computing environment. We present a framework for the implementation of an assurance based competition and demonstrate the competition through a digital chess game. We distinguish our competition from existing models by awarding points for success in a competition domain distinct from, but coupled to cyberspace.