There has been an ongoing debate between the relative deterrent power of certainty and severity on deceptive and criminal activity, certainty being the likelihood of capture and severity being the magnitude of the potential punishment. This paper is a review of the current body of research regarding risk assessment and deception in games, specifically regarding certainty and severity. The topics of game theoretical foundations, balance, and design were covered, as were heuristics and individual differences in deceptive behavior. Using this background knowledge, this study implemented a methodology through which the risk assessments of certainty and severity can be compared behaviorally in a repeated conflict context. It was found that certainty had a significant effect on a person’s likelihood to lie, while severity did not. Exploratory data was collected using the dark triad personality quiz, though it did not ultimately show a pattern.