Sensation seeking is a personality trait that is robustly correlated with delinquent behavior in adolescence. The current study tested specific contextual factors hypothesized to facilitate, exacerbate or attenuate this risk factor for adolescent delinquency. Individual differences in sensation seeking, peer deviance, parental monitoring and self-reported delinquent behavior were assessed in a sample of 470 adolescents. Peer deviance partially mediated the effects of sensation seeking and parental monitoring on adolescent delinquency. We also found evidence for a three-way interaction between sensation seeking, peer deviance and parental monitoring, such that the highest rates of delinquency occurred from the concurrence of high sensation seeking, high peer deviance, and low levels of parental monitoring. Results highlight the importance of considering peer- and family-level processes when evaluating personality risk and problematic adolescent behavior.