We aimed to explore continuity of health care and health barriers, facilitators, and opportunities for people at the time of release from a provincial correctional facility in Ontario, Canada. We conducted focus groups in community-based organizations in a city in Ontario, Canada: a men’s homeless shelter, a mental health service organization, and a social service agency with programs for people with substance use disorders. We included adults who spoke English well enough to participate in the discussion and who had been released from the provincial correctional facility in the previous year. We conducted three focus groups with 18 total participants. Participants had complex health needs on release, including ongoing physical and psychological impacts of time in custody. They identified lack of access to high quality health care; lack of housing, employment, social services, and social supports; and discrimination on the basis of incarceration history as barriers to health on release. Access to health care, housing, social services, and social supports all facilitated health on release. To address health needs on release, participants suggested providing health information in jail, improving discharge planning, and developing accessible clinics in the community. This pilot study identified opportunities to support health at the time of release from jail, including delivery of programs in jail, linkage with and development of programs in the community, and efforts to support structural changes to prevent and address discrimination. These data will inform ongoing work to support health and continuity of care on release from a provincial correctional facility.