The Medicaid Inmate Exclusion Policy (MIEP) prohibits using federal funds for ambulatory care services and medications (including for infectious diseases) for incarcerated persons. More than one quarter of states, including California and Massachusetts, have asked the federal government for authority to waive the MIEP. To improve health outcomes and continuation of care, those states seek to cover transitional care services provided to persons in the period before release from incarceration. The Massachusetts Sheriffs’ Association, Massachusetts Department of Correction, Executive Office of Health and Human Services, and University of Massachusetts Chan Medical School have collaborated to improve infectious disease healthcare service provision before and after release from incarceration. They seek to provide stakeholders working at the intersection of criminal justice and healthcare with tools to advance Medicaid policy and improve treatment and prevention of infectious diseases for persons in jails and prisons by removing MIEP barriers through Section 1115 waivers.