This study examines whether the relationship between violence exposure and school engagement is mediated by psychological problem behaviors and whether such relationships are gendered. Five hundred and sixty-three high school African American adolescents (ages 13–19 years) completed questionnaires that assessed two types of violence exposure (community violence and marital conflict), psychological problem behaviors (e.g., posttraumatic stress disorder symptoms, anxiety, withdrawal, and aggressive behaviors), and school engagement (i.e., student–teacher connectedness and grade point average [GPA] obtained from school records). For male adolescents, psychological problem behaviors collectively mediated the relationship between community violence exposure and student–teacher connectedness. For female adolescents, both community violence and marital conflict exposure were negatively related to both GPA and student–teacher connectedness via aggressive behavior. Findings suggest that the differential impact of type of violence exposure and its sequela based on gender should be considered when addressing low school engagement among African American youth.