School enrollment, mobility, and occupation are each important factors to consider when examining HIV (human immunodeficiency virus) infection risk among youth in sub-Saharan Africa. Through an analysis of narrative life histories from 30 HIV-positive and 30 HIV-negative youth (aged 15-24 years), matched on gender, age, and village and purposively selected and interviewed from the Rakai Community Cohort Study, this article shows the complex connection between leaving school, mobility, and occupation with implications for HIV risk. We identified a pattern of risk factors that was present in many more HIV-positive than HIV-negative youth life stories. These HIV-positive youth shared a similar pathway during their transition to adulthood: After leaving school, they moved in search of occupations; they then engaged in risky occupations before eventually returning to their home village. Linking the lines of inquiry on school enrollment, mobility, and risky occupations, our findings have important implications for adolescent health research, practice, and policy in Uganda and across sub-Saharan Africa and the developing world.