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Pivoting from an era of mass incarceration, the number of individuals being released alongside high recidivism rates remains a concern. In efforts to curb these trends, prior research predominantly focuses on isolating individual-level attributes that correlate with elevated levels of reoffending. Evidence suggests these studies may be over-emphasizing individual explanations at the cost of overlooking the influence of community context and risk. This research revisits and further examines the connections between people, places, and reoffending during reentry. Using panel data from the Serious and Violent Offender Reentry Initiative, this study first assesses the effects of community- and individual-level risk on the likelihood of reoffending, post-release. It then examines the extent to which community risks increase the likelihood of reoffending, net the effect of individual factors. Finally, it explores whether community-level risks interact with individual attributes that, in turn, influence the likelihood of recidivism. Estimates from hierarchical and propensity score matching models reveal that the isolated effect of residing in higher risk communities increases the likelihood of reoffending during reentry, net the significant effect of individual-level risks. Results also suggest that community-level risks interact with and amplify the effect of individual risks in their relation to reoffending after release.