The decade since highly active anti-retroviral therapy (HAART) arrived has been a time of change for gay men in the West. HIV incidence rates have been levelling off--and in some cities, increasing markedly--for the first time since the early years of the pandemic. New sexual subcultures have found expression, including Internet chat rooms, 'poz-only' sex parties, 'barebacking' and crystal methamphetamine use. These circumstances force a re-evaluation of HIV prevention targeting gay communities. We examine the antecedents of current HIV-prevention dilemmas in findings from a qualitative study of gay men who were personally and professionally engaged in HIV/AIDS in Sydney, Australia, in 1997-1998, immediately after the 'protease moment'. The men's lives were characterized by constant and difficult negotiation of gay subjectivities. They did not find a place of uniform belonging in the gay community; rather, ambivalence--toward the gay community and HIV prevention--and fragmentation emerged as themes. Our findings suggest that by the late 1990s, the ethos of safe sex developed in the early HIV/AIDS period was no longer a unifying cultural value. We explore the conditions that led to this shift and the implications for HIV prevention in the 21st century.