Approximately 17% of individuals living with HIV/AIDS pass through the correctional system each year. Jails provide a unique opportunity to diagnose and treat HIV infection among high-risk, transient populations with limited access to medical services. In 2007, the US Health Resources and Services Administration funded a multi-site demonstration project entitled Enhancing Linkages to HIV Primary Care in Jail Settings that aims to improve diagnosis and treatment services for HIV-positive jail detainees and link them to community-based medical care and social services upon release. We performed an evaluation of the Rhode Island demonstration site entitled Community Partnerships and Supportive Services for HIV-Infected People Leaving Jail (COMPASS). Through in-depth qualitative interviews among 20 HIV-positive COMPASS participants in Rhode Island, we assessed how COMPASS impacted access to health care and social services utilization. Most individuals were receiving HIV treatment and care services upon enrollment, but COMPASS enhanced linkage to medical care and follow-up visits for HIV and other co-morbidities for most participants. Several participants were successfully linked to new medical services as a result of COMPASS, including one individual newly diagnosed with HIV and another who had been living with HIV for many years and was able to commence highly active antiretroviral therapy (HAART). While many individuals reported that COMPASS support prevented substance abuse relapse, ongoing substance abuse nevertheless remained a challenge for several participants. Most participants enrolled in one or more new social services as a result of COMPASS, including Medicaid, Supplemental Security Income, food assistance, and housing programs. The primary unmet needs of COMPASS participants were access to mental health services and stable housing. Intensive case management of HIV-positive jail detainees enhances access to medical and social support services and helps prevent relapse to substance abuse. Expanding intensive case management programs, public housing, and mental health services for recently released HIV-positive detainees should be public health priorities.