Research on the association between health insurance coverage and sexual risk behavior among men who have sex with men (MSM) is sparse. We hypothesized that MSM with health insurance would be less likely to engage in risky sexual behavior based on previous research showing that insured persons increase contact with providers which can improve health knowledge, decrease tendency to engage in unhealthy behaviors, and raise awareness about health risks. As part of a study testing an online HIV prevention intervention, we collected information on health insurance and sexual behavior from MSM (n=650). Overall, men with health insurance had a 28% reduced prevalence of unprotected anal intercourse male partners (UAIMP) in the 90 days prior to the survey. Potential explanations include access to healthcare providers and awareness of sexual health. Additional research is needed to identify the mechanism through which health insurance is protective.