Health insurance options available through the Affordable Care Act (ACA) offer new opportunities to enroll individuals involved in the criminal justice system into coverage and provide access to physical and behavioral health services critical to their successful reentry into the community. Many individuals involved in the criminal justice system are now eligible for Medicaid under the ACA, including many young, low-income males who did not previously qualify for Medicaid. With one exception, federal law prohibits using federal Medicaid funds to pay for medical care provided to incarcerated individuals. However, Medicaid enrollment processes can begin prior to an individual’s release from incarceration, as there is no federal prohibition on incarcerated individuals being enrolled in Medicaid and federal law requires states to permit individuals to apply for the program at any time. Drawing on interviews with state officials, this toolkit highlights the efforts of selected states [Colorado, Illinois, New Mexico, Ohio, Rhode Island, Washington, and Wisconsin] to enroll in health coverage individuals involved with the criminal justice system. The toolkit is designed to provide state officials with actionable information about policies and practices available to connect justice- involved individuals to health care coverage through Medicaid." Access is provided to the sections of the Toolkit: the ACA, Medicaid, and justice-involved individuals; policy and process changes; enrollment as part of pre-release planning; post-release outreach; beyond eligibility and enrollment strategies; cross-agency coordination and partnerships; looking forward—future issues to address; state-specific strategies; Webinar: "Corrections and Medicaid Partnerships: Strategies to Enroll Justice-Involved Populations--Efforts in Colorado, New Mexico and Wisconsin"; and links to additional resources. Also presented is the interactive chart "Enrollment Process" which explains where, when, who, how, and whether individuals leave the facility with a Medicaid card. This resource is also available as a PDF chart.