As the global youth population grows exponentially across Africa, there is increasing recognition of the risky health behaviors impeding boys’ healthy transitions through puberty. This study in Tanzania sought to capture boys’ voiced experiences of transitioning through adolescence, and the masculinity norms shaping boys’ engagement in risky behaviors. A critical finding was the gap in parent-son communication around pubertal body changes and avoidance of risk behaviors. Findings also suggest influences from globalization and modernization are changing boys’ pubertal experiences and introducing new challenges for parents attempting to provide guidance. Given evidence from high-income countries indicating parents can serve as protective factors for young people during the transition through adolescence, additional research is needed to understand current parent-son dynamics and potential interventions.