As a group, delinquent youth complete less education and show poor academic outcomes compared to their non-delinquent peers. To better understand pathways to school success, this study integrated individual- and neighborhood-level data to examine academic functioning among 833 White, Black, and Hispanic male juvenile offenders (age 14-17) living in two urban communities. A multilevel path analysis confirmed that youth in relatively more affluent communities report greater access to opportunities in the areas of education and employment, and that these opportunities are associated with higher expectations to succeed and better grades. Findings highlight the importance of taking an ecological approach for understanding processes that shape school effort and achievement. Implications are discussed in the context of promoting academic success among juvenile offenders, specifically, and for understanding pathways to healthy adjustment, more generally.