Data sharing and interoperability between jail systems and community health providers are critical for successful re-entry of incarcerated individuals into the mainstream community. Using a case study approach, we present an account of interoperability efforts between jail and community health systems in the County of Orange (California, USA), including the overall infrastructure comprising of the jail management system, jail health system, and the community health system. We also describe outcomes and lessons from the Jail to Community Re-entry Program implemented in the County of Orange, along with recommendations and common data elements required for effective care transitions from custody to community