This study recruited 559 youths from detention centers (mean age was 15.4 years; 50.1% of detainees were girls) to investigate pathways that link witnessing community violence in the 12 months before detainment to drug and sexual risk behaviors in the two months preceding detainment. Through the use of audio-computer-assisted technology, data were collected on demographics, family factors, peer influences, religiosity, witnessing community violence, and drug and sexual risk behaviors. When controlling for demographics and family variables, the authors found positive associations between witnessing community violence and drug and sexual risk behaviors. Witnessing community violence was directly linked to sexual risk behaviors and indirectly associated with these risk behaviors and substance use through gang membership and perceived risky peer norms. Findings suggest that interventions targeting change in peer affiliations and perceived norms may be an effective strategy for reducing risky drug and sexual behaviors among detained youths.