Previous research indicates high rates of HIV infection among male-to-female transgender persons. Although HIV incidence is high, there is a dearth of information on how male-to-female transgender persons are at risk for HIV; furthermore, little to no research has been conducted on how male-to-female persons manage living with HIV. In Fall 2003, I conducted 20 in-depth interviews with a group of male-to-female transgender individuals from a community clinic in New York City. The primary aims of this study were to:explore the relationship between gender roles and HIV risk behaviors within the contexts of transgender-related stigmatization and violence, drug use, and survival sex and to identify facilitators and barriers to health care. Data indicate that there is a very real need to better train medical professionals to deal with transgender health care needs. Although most of the participants were happy with the services they received at the clinic, they also described a number of incidents and preferences that impeded their access to proper health care prior to arriving at this clinic. Of particular concern is the ability of doctors to provide a wide range of services ranging from hormone therapy to HIV medication.