Despite significant financial and human resources mobilized to manage current infections and prevent new cases HIV prevalence remains high in South Africa. The intractability of HIV has resulted in calls for the implementation of novel HIV prevention strategies (UNAIDS 2013) such as Voluntary Medical Adult Male Circumcision (VMAMC) as a part of a comprehensive HIV prevention intervention. Whether traditionally practiced or not male circumcision is powerfully implicated in meanings of masculinity in South Africa. The national rollout of VMAMC tensions traditional masculinity against various biomedical apprehensions particularly in the language and logic of HIV prevention. As such this paper explores how this tension is negotiated in participants perceptions of VMAMC as a South African public health intervention. Semistructured repeat interviews conducted with 30 adult men from Johannesburg were analyzed using a Straussian grounded theory approach. Three primary categories revealed that meanings of masculinity within the context of VMAMC are underpinned (a) by adopting an active role in the fight against HIV in South Africa (b) as understanding the tension between tradition and medicine and/or (c) by using tradition as a means to reappropriate or reject the practice. These categories suggest that the removal of the foreskin cannot simply be reduced to a biomedical practice on or related to male bodies assumed to be unmediated by culture and history. These findings hold significant implications for the implementation of a national VMAMC HIV prevention program in South Africa.