In two studies we investigate gender differences of cheating in online versus in-person environments. Theory suggests online anonymity increases social distance and therefore results in higher cheating (Chatness et al., 2007). Cheating also increases over time (Garrett et al., 2016), but previous findings concerning gender differences are inconsistent (Gerlach et al., 2019). Study one: 137 participants (online: n=75, in-person: n=62; balanced gender distribution) completed a fine-motor tracing task in four sessions. Individuals made a performance prediction before each trial prior to competing against each other for the highest scores. Not achieving the predicted score resulted in a loss of all points for this trial. Cheating was measured as the difference between self-reported and expert-rated errors. Findings suggest greater cheating for men as compared to women in the online condition, when cheating prevented them from losing their points. In addition, cheating increased over time in the online condition, especially in men. Study two: 144 participants (online: n=71, in-person: n=63; balanced gender distribution) completed the “Difference Spotting Task”, a cognitive measure to assess cheating at the individual level (Liu et al., 2021). Cheating was measured by the number of unsolvable items a participant claims to have solved. Findings show higher cheating for men as compared to women in the online condition. This suggests that online contexts may reduce certain internal and social checks on dishonesty, such as concerns about self-image or accountability, potentially allowing some individuals to engage in cheating with fewer perceived consequences compared to in-person settings.