This study examined the link between developmental risk and protective factors and risky sexual activity among 222 urban African American youth attending an alternative education program (AEP) because of problematic behavior. Self-report information provided by these AEP participants revealed that, for the risk and protective factors examined, the extent of their involvement in delinquent activity, including substance use, and the less parental monitoring they received were the principal correlates of both the likelihood of the initiation and extent of their engagement in risky sexual activity. Findings of the study also illustrate the feasibility of the early identification of individuals likely to be at increased risk for the development of sexually-related short and long-term adverse health outcomes.