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Adolescents who become involved in the juvenile legal system are at significant risk of lifelong juvenile and criminal legal system involvement. While we understand many individual risk factors related to adolescent recidivism, contextual risk factors (CRFs) are less often examined. This analysis focused on a sample of youth from the western United States who had been arrested at least once (n = 293). Using a hierarchical logistic regression, we examined CRFs that may be associated with adolescent recidivism (defined as more than one arrest during adolescence). CRFs were selected using an ecological perspective and entered into the model in order of proximity to the adolescent. Categories included family (parent/child dyadic coercion, parental monitoring, family conflict), peer (peer coercion, deviant peer association, peer deviant talk), school (learning environment, perceived danger, perceived antisocial behavior), and sociodemographic (family income, race, gender). The final model explained 26% of the variance in recidivism likelihood, with the peer and sociodemographic spheres explaining significant variance in recidivism. Specifically, higher deviant peer association and lower family income were significantly associated with recidivism likelihood. These findings stress the importance of context in recidivism risk and encourage attention to these factors in decision-making in the juvenile legal system.