While the HIV epidemic is resurging in gay communities worldwide, HIV notification rates remain stable in NSW. This outcome demonstrates the success of a well-funded partnership approach to preventing HIV infection in gay men in NSW. However, population rates of new diagnoses of HIV are similar to those seen in comparable countries and sexual risk-taking may be increasing. As the HIV epidemic has evolved, prevention in gay men has become more complex and must effectively engage with an increasing diversity of risk reduction strategies. These strategies reflect the continual adaptation of the gay community to evolving understandings of the HIV epidemic and the diverse ways in which gay men balance pleasure and prevention.