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Many people in jail have serious health needs that can contribute to a cycle of relapse and recidivism, but a recent pilot in Connecticut found that those who left jail with Medicaid coverage availed themselves of outpatient services, prescription medicines, and behavioral health care, often within one month of release. This report details how jail staff worked with Medicaid to implement an enrollment procedure and describes the challenges in conducting enrollment with pretrial detainees given their short stays in jail. Findings suggest that suspending rather than terminating Medicaid coverage when people enter jail, as well as automatically reinstating Medicaid upon release, can increase continuity of care for this high-risk population. Doing so may enhance the health prospects of individuals leaving jail and potentially reduce recidivism, while also minimizing the burden on hospitals of preventable emergency room visits.