HIV/AIDS remains a substantial health threat to men who have sex with men. Although new HIV medications have provided great benefits for many HIV-positive individuals, they have done little to protect HIV-negative men. Consequently, changing one's sexual practices remains the most effective way to reduce risk for HIV. However, to develop an effective intervention for reducing HIV risk, it is important to fully understand risk behavior. In this article, we detail the essential elements for conducting an HIV risk assessment as well as those contextual factors that may support risk behaviors. Further, we discuss the importance of procuring an HIV test and the critical issues that may arise because of testing for HIV as well as the critical issues that may result from testing HIV-positive. Finally, we illustrate how we integrate an HIV health risk assessment into a clinical interview. © 2001 John Wiley & Sons, Inc. J Clin Psychol/In Session 57: 655–669, 2001.