The research objectives of this study are to describe the re-entry experiences of people recently released from jail who were living with HIV/AIDS, and to identify factors that influence their access to primary care and adherence to a treatment regimen. The research used a mixed-method, qualitative and quantitative research design. The findings indicate that the overall instability in the lives of many of the former inmates studied hampered their ability to attend to their HIV/AIDS-related health care needs. Most former inmates returned to the community with co-occurring problems related to housing and substance abuse. Complicating their access to health care were fragmented health care and correctional systems. The study highlights the need for coordination and collaboration between correctional facilities and community-based health care and human service providers that leads to a deliberative and planned transition from jail to service systems in the community.