This article describes challenges of conducting an HIV prevention program involving 40 male and female participants ages 12-18 in Hammanskraal, South Africa, aimed at increasing awareness and knowledge of laws protecting children's sexual health rights and access to services through a culturally based "study circle" format. Challenges highlighted by the project included Institutional Review Board approval of youth consent procedures, cooperation and coordination with local policymakers, the need to modify presentation materials to youths' comprehension levels, availability of youth-based sexual health service providers, and cultural ambiguity over parental involvement in youth health care decisions and laws pertaining to sexual relationships among minors.