Some prior studies have found that, for boys, earlier puberty is linked to higher crime and delinquency, while other studies have found that earlier puberty is associated with greater social competence and beneficial psychosocial development. The current study suggests that these seemingly contradictory results actually represent two divergent pathways by which earlier pubertal timing can affect adjustment. Which pathway boys take is highly dependent on psychosocial context. Using a sample of 310 African American boys and their primary caregivers tracked across three waves of data collection from ages 10.55–18.84 from the Family and Community Health Study (FACHS), the current study utilizes Latent Moderated Structural Equation Modeling (LMS) to analyze effects of interactions between pubertal timing and social contextual factors on criminal behavior and social competence. Results suggest that criminogenic effects of early puberty are contingent on deviant peer group, poor school experience, harsh parenting, and neighborhood disorganization, whereas the association between earlier puberty and social competence is attenuated by harsh parenting. Results suggest that modeling both positive and negative development outcomes together may give a clearer picture of the developmental consequences of pubertal timing for boys. In addition, this study shows the importance of social context in shaping the meaning and consequences of biological variables like pubertal timing.