This article reports on a program of research that examined the background, planning, implementation, and evaluation of an after-school preventive intervention program within an ongoing urban alternative education program targeting African American students referred to the school because of their problematic behavior in regular schools. The research undertaken involved the examination of three separate, but interrelated, investigative components: (a) the relationship of risk and protective factors to the sexual activity of individuals in the targeted population; (b) the problems associated with the implementation of an after-school preventive intervention found to be effective within a regular school setting; and (c) determination of the effectiveness of the after-school preventive intervention, the results of which were largely compromised by the problems encountered during the implementation of the intervention.