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Prior research shows that certain personality traits as well as exposure to delinquent peers increase offending risk (Pratt et al., 2010; Jones et al., 2011). Moreover, prior work has shown that personality traits and delinquent peers are related in a causal process, such that traits affect the formation of delinquent peer relationships which then serve to encourage criminal behavior (e.g., Chapple, 2005). The current study seeks to expand this line of work by investigating the mediating role of delinquent peers between the Big Five personality traits and offending. In addition, it examines the conditional nature of these indirect effects (often referred to as “moderated mediation”). To this end, several research questions are posed. First, do delinquent peers mediate the relationship between the Big Five personality traits and offending? Second, are these indirect effects contingent on delinquent peer influence? Third, and relatedly, are these indirect effects contingent of resistance to delinquent peer influence? These research questions are addressed using a sample of adjudicated youth in the Pathways to Desistance Study.