The present contribution examines two factors, as well as their interplay, prominently discussed in the literature on cheating: The basic personality trait of Honesty-Humility from the HEXACO personality model and cues of being watched when given the possibility to cheat. In two studies (Study 1 N = 192, Study 2 N = 957), we applied economically incentivized cheating paradigms (a dice-rolling paradigm and a coin-toss paradigm) and replicated the previously found negative relation between Honesty-Humility and cheating behavior. We further demonstrated that this relation holds beyond the dark personality traits of narcissism, Machiavellianism, psychopathy, and sadism (i.e., the Dark Tetrad). In fact, Honesty-Humility fully absorbed the positive correlations of Dark Tetrad dimensions and cheating. However, we failed to obtain statistically significant results with respect to the other analyzed factor: manipulating being watched by presenting stylized watching eyes when individuals could cheat did not significantly affect cheating behavior. We further found no significant interaction between the personality factors and the presentation of stylized eyes. The findings are discussed with regard to current debates in the fields of cheating and personality as well as when being watched alters behavior.