This study assessed the prevalence of self-reported HIV infection among a community sample of transgender women and identified associated contextual, experiential, and behavioral factors. Ninety-two transgender women completed a self-administered interview. Recruitment occurred through an LGBT service organization, a transgender support group, transgender advocates, and informal communications. Eighty-two percent were African American/Black. Of 83 who knew their status, 60% reported being HIV infected. High rates of childhood sexual abuse (52%), rape (53%), intimate partner violence (56%), and incarceration (57%) were reported. Many did not have health insurance (53%), were not employed full-time nor in school (63%) and had been recently homeless (49%). HIV-infected transgender women as compared to HIV-uninfected transgender women were more likely to be African American/Black (P = 0.04), and older than 34 years (P = 0.01), unemployed/not in school (P < 0.001). HIV-infected transgender women also experienced less trans-related discrimination (P = 0.03), perceived less negative psychosocial impact due to trans status (P = 0.04) and had greater happiness with their physical appearance (P = 0.01). HIV-infected transgender women may experience relatively less trans-related stress compared to their HIV-uninfected counterparts. High rates of HIV, trauma, and social marginalization raise concerns for this population and warrant the development of structural and policy-informed interventions.