This brief provides an overview of initiatives to connect the justice-involved population to Medicaid coverage and care in the community in three states—Arizona, Connecticut, and Massachusetts—based on interviews with key stakeholders. These states are leading efforts in these areas and provide key lessons about how to coordinate across health care and corrections and the potential of such initiatives to better link individuals to the physical and behavioral services they need. Each of the case study states is connecting individuals to coverage at multiple points within the justice system. The study states also connect individuals to care in the community as they are released from jail or prison. Stakeholders and data indicate that these approaches have increased coverage, facilitated access to care, and contributed to administrative efficiencies and state savings. However, more data and time are needed to examine the effects on health and criminal justice outcomes, including recidivism rates.