In response to higher perceived risks of HIV infection in the education sectors, many sub-Sahara African countries have school- and community-based HIV/AIDS awareness (SCBHA) and school-based HIV/AIDS support (SBHS) initiatives. Using ordinal logistic and Rasch scaling, this study utilizes the Southern and Eastern Africa Consortium for Monitoring Educational Quality (SACMEQ) data to predict the strength and direction of the associations between school- and community-based initiatives and the perceived risk of HIV infection reported by head teachers. Findings indicate SCBHA and SBHS significantly predict the odds of the perceived risk of HIV/AIDS infection. Sociodemographic and contextual factors confound some of the associations.