This study examines the joint impact of social contexts and social influences on adolescent development by examining contextual systems, such as peers, parents, school, and community. Participants included 14,548 middle school students comprised of 78.6% White, 5.4% Biracial, 4.8% Asian, 4.8% Black, and 3.6% Hispanic. Participants completed a survey with scales assessing risk behaviors (sex, substance use, and delinquency), peer influence, parental influences, and characteristics of their school and community. Hierarchical Linear Modeling was used to consider the variation of parental and peer influences on risk behaviors while evaluating the influences of school and community. Results indicated that all Level 2 variables (school climate, positive sense of community, community resources, extracurricular involvement) influenced the school mean level risk behaviors. Results also showed that contextual variables moderated the relationship between peer and parental influence on risky behaviors, thereby acting as protective factors. The findings of the current research are important because they inform a more complex theoretical understanding of adolescent development and they identify specific contextual factors that can be fostered with appropriate programs and interventions to reduce negative development in adolescence.