Previous research suggests that incarceration can have a negative effect on health. These health effects have an especially profound impact on HIV-positive individuals. As such, the current study investigates how incarceration affects the health of 12 African American HIV-positive formerly incarcerated males recruited via an AIDS Service Organization. Individuals were enrolled via purposive sampling and engaged in a series of indepth interviews over a yearlong period (n = 46). Participants ranged in age from 33 to 61 years. Most had finished high school, were not employed at time of first and last interview, and most were primarily residing at a homeless shelter. The time incarcerated ranged among participants from 3 months to 3 years. Findings suggest that health is impacted via limited and delayed access to medication, stigma, and poor quality of medical care while incarcerated. Health continues to worsen after release, largely due to incarceration's impact on individuals' social context. Macro-level policy limits opportunity to fulfill basic needs such as housing and hinders one's ability to be gainfully employed. Moreover, stigma, loss of social support, and a delay in accessing HIV-related services deleteriously impacts individuals' mental and physical health status. Implications for practice, policy and future research are also discussed.