Despite substantial research on cheating, how and when individual predispositions figure into cheating behavior remains unclear. In Study 1, we investigated to what extent Honesty-Humility predicted cheating behavior. As expected, individuals high on Honesty-Humility were less likely to cheat than were individuals low on this trait. In Study 2, integrating arguments from personality research about traits with arguments from behavioral ethics about moral primes, we examined how Honesty-Humility and situational primes interacted to affect cheating. We found an interaction indicating that individuals high on Honesty-Humility consistently did not cheat much across situational primes, whereas individuals low on Honesty-Humility cheated more when exposed to immoral primes than when exposed to moral primes. Our research invites reflection about the interplay of individual differences in Honesty-Humility and situational cues in predicting cheating, including the design of anti-cheating systems and the context in which these person and situation factors interact.