In the light of the potential negative consequences of dishonest behaviors for individuals and societies, researchers from diﬀerent disciplines have aimed to investigate situation and person factors shaping the occurrence and extent of such behaviors. The present study investigates the roles of a situation factor, the baseline probability of observing a favorable outcome, and a person factor, trait Honesty-Humility from the HEXACO Model of Personality, in shaping dishonest behavior. Next to main eﬀects, a person-situation interaction between these factors was tested. Across three studies with 5,297 participants overall, we ﬁnd that a higher baseline probability of observing a favorable outcome and lower levels in Honesty-Humility are linked to more dishonest behavior, whereas there was no strong evidence for an interaction between these factors. By testing the assumed eﬀects in two diﬀerent cheating paradigms, this study additionally allows to disentangle previously found eﬀects of (a) the distance between an observed and the favorable outcome and (b) the baseline probability of observing a favorable outcome.