Scope and Method of Study: This study examined adolescents' perceptions of contextual risks (neighborhood risk or peer delinquent behavior) and connectedness (neighborhood cohesion, family cohesion, mothers' support, and fathers' support) in association with adolescents' reports of delinquent behavior in a predominately Latino and African American sample of 9th and 10th grade students. Data were collected from 688 adolescents (mean age of 14.9; 23.5% African American, 53.1% Latino, 14.2% Caucasian) in three states. Hierarchical multiple regression analyses were used to separately examine--for neighborhood risk and peer delinquent behavior--a theoretical model which posited that (a) risks would be positively associated, while aspects of connectedness would be negatively associated to adolescents' reports of delinquent behavior and (b) aspects of connectedness would moderate the association between the risk and adolescents' delinquent behavior-. Slope analysis was used to determine significance of moderating associations.Findings and Conclusions: In both the neighborhood risk and peer delinquent behavior models, risk was positively associated, while aspects of connectedness were negatively associated with adolescents' delinquent behavior. In the neighborhood risk model, mothers' support moderated the deleterious association with delinquent behavior, particularly for boys. For youth reporting high family cohesion, fathers' support afforded protection against delinquent behavior. In the peer delinquent behavior model, boys were at greater risk for delinquent behavior when reporting high peer delinquent behavior. The positive association of peer delinquent behavior and adolescent delinquent behavior was moderated by fathers' support x gender, showing the greatest protective potential for boys. In sum, connectedness at the parental and family levels buffers the risks of peer delinquent behavior and neighborhood risk for adolescents' delinquent behavior. Future research can include an investigation into additional domains of connectedness (e.g., school, peer) within various risk contexts. For prevention and intervention programming, the need for the inclusion of parents and family in treatment is highlighted