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This study examined HIV-related health risk behaviors–unprotected anal intercourse, alcohol intoxication, and drug use–and their association with stigma in a sample of transgender women. We conducted a cross-sectional survey of 191 transgender women recruited through purposive sampling in San Francisco, CA. Unprotected anal intercourse, alcohol intoxication, and illicit drug use were significantly intercorrelated, suggesting the presence of a “syndemic” among these HIV-related behavioral health risks. In multivariable analyses controlling for sociodemographic and individual health characteristics, stigma was independently associated with greater levels of unprotected anal intercourse, illicit drug use, and a composite index of the 3 risk behaviors. Findings highlight a need for interventions to address stigma and the social context of unprotected sex, alcohol intoxication, and drug use, which may contribute to HIV risk among transgender women.