The aim of this analysis was to examine gay men's sexual risk practice to determine patterns of risk management. Ten cross-sectional surveys of gay men were conducted six-monthly from February 1996 to August 2000 at Sydney gay community social, sex-on-premises and sexual health sites (average n = 827). Every February during this period, five identical surveys were conducted at the annual Gay and Lesbian Mardi Gras Fair Day (average n = 1178). Among the minority of men who had unprotected anal intercourse which involved ejaculation inside with a serodiscordant regular partner, there was a clear pattern of sexual positioning. Few regular couples were both receptive and insertive. Most HIV-positive men were receptive and most HIV-negative men were insertive. Among the minority of men who had unprotected anal intercourse which involved ejaculation inside with casual partners, there was also a pattern of sexual positioning. Whereas many casual couples were both receptive and insertive (especially those involving HIV-positive respondents), among the remainder HIV-positive men tended to be receptive and HIV-negative men tended to be insertive. These patterns of HIV-positive/receptive and HIV-negative/insertive suggest strategic risk reduction positionings rather than mere sexual preferences among a minority of gay men. If so, they point not to complacency but to an ever more complex domain of HIV prevention.