Objective: This study examined the relationships between community violence exposure and two related, but meaningfully distinct, academic outcomes: school engagement and academic achievement (grade point average, GPA). Psychological symptoms were investigated as mediators of these relationships. Method: One-hundred and eighteen youth reported on community violence exposure and school engagement twice during adolescence, and both parents and adolescents reported on psychological symptoms. Cumulative GPA was also acquired from participants. A path model and hierarchical multiple regression analyses were used to assess these relationships longitudinally. Results: Earlier community violence exposure inversely predicted later school engagement, but earlier school engagement did not predict later community violence exposure. School engagement mediated the association between community violence exposure and school GPA. Internalizing and externalizing symptoms, but not posttraumatic stress symptoms, mediated the association between community violence and school engagement. Conclusions: When adolescents are exposed to community violence, they may become vulnerable to a cascade of events including psychological symptoms and decreased connectedness to school, which ultimately can lead to overall poor academic achievement. The more proximal, changeable experiences of school connectedness and psychological symptoms offer targets for interventions offsetting long-term adverse academic consequences in violence-exposed youth. (PsycINFO Database Record (c) 2013 APA, all rights reserved)