Despite much research, skepticism remains over the possibility of profiling scholastic cheaters. However, several relevant predictor variables and newer diagnostic tools have been overlooked. We remedy this deficit with a series of three studies. Study 1 was a large-scale survey of a broad range of personality predictors of self-reported cheating. Significant predictors included the Dark Triad (Machiavellianism, narcissism, psychopathy) as well as low agreeableness and low conscientiousness. Only psychopathy remained significant in a multiple regression. Study 2 replicated this pattern using a naturalistic, behavioral indicator of cheating, namely, plagiarism as indexed by the Internet service Turn-It-In. Poor verbal ability was also an independent predictor. Study 3 examined possible motivational mediators of the association between psychopathy and cheating. Unrestrained achievement and moral inhibition were successful mediators whereas fear of punishment was not. Practical implications for researchers and educators are discussed.