Imprisonment provides opportunities for the diagnosis and successful treatment of HIV, however, the benefits of antiretroviral therapy are frequently lost following release due to suboptimal access and utilization of health care and services. In response, some have advocated for development of intensive case-management interventions spanning incarceration and release to support treatment adherence and community re-entry for HIV-infected releasees. We conducted a randomized controlled trial of a motivational Strengths Model bridging case management intervention (BCM) beginning approximately 3 months prior to and continuing 6 months after release versus a standard of care prison-administered discharge planning program (SOC) for HIV-infected state prison inmates. The primary outcome variable was self-reported access to post-release medical care. Of the 104 inmates enrolled, 89 had at least 1 post-release study visit. Of these, 65.1% of BCM and 54.4% of SOC assigned participants attended a routine medical appointment within 4 weeks of release (P > 0.3). By week 12 post-release, 88.4% of the BCM arm and 78.3% of the SOC arm had at attended at least one medical appointment (P = 0.2), increasing in both arms at week 24–90.7% with BCM and 89.1% with SOC (P > 0.5). No participant without a routine medical visit by week 24 attended an appointment from weeks 24 to 48. The mean number of clinic visits during the 48 weeks post release was 5.23 (SD = 3.14) for BCM and 4.07 (SD = 3.20) for SOC (P > 0.5). There were no significant differences between arms in social service utilization and re-incarceration rates were also similar. We found that a case management intervention bridging incarceration and release was no more effective than a less intensive pre-release discharge planning program in supporting health and social service utilization for HIV-infected individuals released from prison.