Certain populations of people living with HIV (PLWH) are at greater risk for falling out of care, including PLWH with a history of incarceration. This is associated with increased risk of morbidity and mortality. In the current retrospective cohort study, we examined patient-level information for 340 PLWH who had transferred HIV care services from prison or from other community-based or private HIV primary care providers to a large urban HIV clinic in the southeastern United States. Results indicated that, compared to those transferring care from another community-based or private medical provider, PLWH transferring care from prison were significantly less likely to be retained in care than PLWH transferring care from other providers, even after controlling for other factors. HIV primary care social workers, who are trained to provide case management services, can help provide PLWH with a coordinated continuum of care that addresses the complex issues faced post-release.