Since the introduction of highly active antiretroviral therapy, people living with HIV/AIDS (PLWHA) are living longer, into older age, and therefore presenting a host of new challenges for health and social service providers. However, not all PLWHA are likely to experience similar transitions into older age. In particular, research has yet to fully investigate the health and psychosocial well-being of older HIV-positive gay men. Drawing from an Australian population-based sample of 693 HIV-positive gay men, the present study assesses the overall health and well-being of this older group compared to their younger counterparts. While older men reported greater comorbidity and were more likely to be living in poverty, other health and well-being indicators suggest this group to be coping comparatively well as they continue to age with HIV. These findings provide new directions for meeting the present and future needs and challenges of older HIV-positive gay men.