Many states have expanded Medicaid eligibility to reach a wider array of vulnerable and historically uninsured populations. While Medicaid cannot pay for medical services provided in prisons or jails, people who are arrested and incarcerated can enroll in Medicaid and become eligible for benefits in the community. Given the high prevalence of mental health issues, substance abuse, and chronic health conditions among criminal justice populations, providing health care services to them could improve public health and public safety outcomes. This brief highlights initiatives in Connecticut and Rhode Island to ensure continuous access to needed medication for justice-involved people.