The central goal of this longitudinal study was to develop a laboratory-based index of children's covert cheating behavior that distinguished normative rule violations from those that signal risk for antisocial behavior. Participants (N = 215 children) were drawn from a community population and oversampled for externalizing behavior problems (EXT). Cheating behavior was measured using two resistance-to-temptation tasks and coded for extent of cheating, latency to cheat, and inappropriate positive affect. Mothers rated internalized conduct and three forms of self-regulation: inhibitory control, impulsivity, and affective distress. Mothers and teachers reported EXT concurrently (T1) and 4 years later, when children averaged 10 years of age (T2). Children categorized as severe cheaters manifested lower inhibitory control, greater impulsivity, and lower levels of internalized conduct at T1. Children in this group also manifested higher levels of EXT in home and school settings at T1 and more EXT in the school setting at T2, even after accounting for T1 ratings. (Contains 5 tables.)