Use of electronic health records (EHRs) is an important innovation for patients in jails and prisons. Efforts to incentivize health information technology, including the Medicaid EHR Incentive Program, are generally aimed at community providers; however, recent regulation changes allow participation of jail health providers. In the New York City jail system, the Department of Health and Mental Hygiene oversees care delivery and was able to participate in and earn incentives through the Medicaid EHR Incentive Program. Despite the challenges of this program and other health information innovations, participation by correctional health services can generate financial assistance and useful frameworks to guide these efforts. Policymakers will need to consider the specific challenges of implementing these programs in correctional settings.