This paper uses the qualitative unstructured interviews and Focus Group Discussions (FGD) to understand how Bamasaaba men conceptualise masculinity in response to safe medical male circumcision (SMMC) in Ugandan. Results were obtained from cultural leaders, clan leaders, traditional surgeons, medical officers, 2016 initiates, focus groups and the key informant, a representative of Inzu ya Masaaba. Processing the audio recorded responses and data analysis involved transcribing, interpreting, coding, and categorising using Atlas Ti software. The results of the study suggest ambivalence. The historical and political attempts to abolish TMC have evoked resistance, with most holding firmly to TMC as the only means by which Bamasaaba boys can acquire the status of manhood. However, some men see health values in medicalised male circumcision practices and believe that medicalisation has caused positive adaptations to TMC for purposes of enhanced hygiene and safety.