The correlation between victimization and offending (i.e., the victim–offender overlap) is one of the most documented empirical findings in delinquency research, leading researchers to investigate potential contingencies in this relationship. A small number of studies have found evidence of contextual variation in the victim–offender overlap, but these studies have produced conflicting results as to whether urban context amplifies or attenuates this relationship. To add clarity to this body of literature, the present study uses a nationally representative sample of adolescents from the National Longitudinal Study of Adolescent Health (Add Health) to investigate potential variation in the victim–offender overlap across school context. Results indicate that victimization is positively and significantly related to offending in all school contexts but that the relationship between victimization and offending is stronger in non-urban schools than in urban schools. Results also indicate that negative emotionality may play a key role in unpacking the mechanisms through which context moderates the victim–offender overlap.