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Differential association theory and the closely linked differential coercion / social support theory both suggest that peers can exert both criminogenic and non-criminogenic influences on individuals. While prior work demonstrates that peers provide both supportive and detrimental influences to reentering persons, little is known about how each dimension affects reentry outcomes independently or interdependently. Using reentry data, this study investigates the role of both peer support and peer criminality on substance use and criminal offending over time. Mixed-effects models demonstrate that peer criminality relates to significantly higher odds of substance use and criminal offending. Peer support, on the other hand, relates to significantly lower odds of substance use and criminal offending. Interaction terms between peer support and peer crime suggest the two constructs exert independent, but not interactive, influences on recidivism. The results, which support both differential association and social support perspectives, demonstrate that although peer criminality exerts a more robust effect on recidivism, peer support must be understood as an important mechanism that drives desistance independently of a peer’s offending behaviors.