Although progress has been made toward reducing risk-taking behavior among teens, adolescents confined in juvenile detention facilities and youths living in inner cities remain vulnerable. Reaching these populations with appropriate risk-reduction strategies continues to challenge health providers and educators. Crucial first steps in the design of relevant programs involve discovering how at-risk teens perceive risk and which risks and dangers within their communities occupy their attention. Participants in this study did not identify HIV/AIDS as a primary concern; instead, they described the dangers and risks they encountered in their home neighborhoods. Based on these findings, this discussion addresses the implications for the development of health education programs to empower teens for responsible behavior after release from detention.