Adolescents are vulnerable to becoming involved in problematic behaviors, disengaging academically, and dropping out of school. This study was designed to evaluate the protective role of self-perceived school attachment and family involvement on the development of these negative behaviors during adolescence. The Social and Health Assessment (SAHA) survey was conducted among 652 predominantly minority, inner-city adolescents during their transition from middle to high school in order to examine school attachment, perceived teacher support, parental control, and exposure to community violence as predictors of engagement in violent activities, development of aggressive beliefs, perception of school climate, and academic motivation one year later. Family and school factors appeared to be differentially associated with the negative outcomes. School attachment was associated with lower levels of violent delinquency and aggressive beliefs, as well as with academic motivation. Perceived teacher support was associated with positive perceptions of school climate and with academic motivation. Parental control was associated with lower levels of violent activity and with higher levels of academic motivation. Violence exposure was related to violent delinquency and negative perception of school climate. School attachment, teacher support, parental control, and violence exposure must all be incorporated into school reform efforts intended to break the inner city cycle of violence.