Worldwide, HIV has disproportionally affected incarcerated populations since early in the epidemic. Current trends in the Caribbean demonstrate that correctional facilities house most at-risk individuals. The experience of incarceration and the HIV epidemic in the Caribbean are as diverse as the region. In this paper we present descriptive information from Puerto Rico and Jamaica as two unique examples of current efforts to address HIV among prisoners. While different, these countries provide a comparison of correctional health care in a sexually driven epidemic versus one where injecting drug use plays a major role, bridging cultural differences, and contrasting approaches in the provision of HIV services relevant for other Caribbean countries. While the evidence of effective interventions within correctional facilities in the Caribbean is limited, the knowledge gained through the services implemented and research completed in different countries can facilitate the process of developing and testing new interventions. The experience of these islands and coordinating lessons learned and innovations from throughout the region can assist in developing a resourceful way forward.