From early in the epidemic, education has been central to HIV prevention, treatment, and care. This paper reflects on lessons learned over the last 30 years. It signals the limits of high level international commitments to education and HIV and the strategies of information-giving and life skills development adopted in their wake. It argues for the adoption of a more genuinely educational approach to HIV, sex, and sexuality education in which difficult questions are raised, diversity is recognized, and options are provided for a differentiated yet effective response. The lead currently offered by community organizations and the social media should be built upon in developing forms of HIV education that are more honest and contextually relevant than previously.