Before Connecticut’s 2016 Medicaid policy change, people placed in the state’s halfway houses as part of their reentry preparation had to return to jails and prisons to receive health care. This qualitative brief describes how residents and staff experienced and perceived the transition to Medicaid in access to care, health care usage, and program operations. We found that access to community-based care is a substantial improvement, because returning to jail deterred residents from seeking care and was logistically burdensome. Residents appreciated easier access to care and higher care quality, while staff perceived less burden with no additional risk. Yet, Medicaid income eligibility limits, provider availability, and halfway house pass policies have posed challenges. We suggest ways to improve links to community-based care and are conducting ongoing research assessing whether Medicaid access affected rates of health care usage and criminal reoffending.