Why do so many adolescents cheat despite judging that cheating is wrong? Two studies tested a new model of cheating in high school. In Study 1, 85 high schoolers in the Western U.S. reported their perceptions, evaluations, and motivations surrounding their own and hypothetical cheating. In Study 2, 83 teachers reported their views about cheating; we also analyzed course syllabi. About half of the adolescents reported unintentional cheating, and many judged their own cheating—but not hypothetical cheating—as acceptable. Decisions to cheat were responses to competing pressures, low value placed on the assignment, and other considerations. Study 2 revealed teacher‐student disagreements about cheating, and minimal content about academic integrity in syllabi. The findings supported the proposed model of adolescent cheating.