Background: To date, whilst there have been many published studies exploring the links between masculinity and HIV, not much work has been done to explore how an HIV-positive diagnosis impacts men's sense of masculinity and contextualizing the masculinities as fluid and changing. Objective: To explore how human immunodeficiency virus (HIV) impacts the lives of men and their constructions of masculinity through interviews with 18 men living with HIV. Design: Qualitative study involving conveniently and purposively selected black South African adult men who lived with HIV. In-depth interviews were conducted with 18 men who resided in Johannesburg and Mthatha, South Africa. Results: Our analysis suggests that the performance of risky masculinity may influence the acquisition of HIV. Yet, it also reveals that HIV can have a significant effect on men and their masculinities. Men's constructions of harmful notions of hegemonic masculinity pre-HIV diagnosis negatively affected their help-seeking behavior and coping and adjustment to living with HIV, post-diagnosis. The dominant discourse that men are strong and healthy visibly presented challenges for men when faced with an HIV-positive status. They interpreted HIV diagnosis as a loss, a sign of failure as a man, and evidence of an inability to retain control. Being sick undermined their ability to perform roles expected of them, and this led to feelings of powerlessness, worthlessness, and distress. Conclusions: Interventions with men living with HIV need to provide safe spaces for men to critically explore gender and constructions of social identities and the pressures these place on men and implications for their health. With this approach, harmful constructions of masculinities may be challenged and mitigated, and this process may render men amenable to change.