This case study examines Long Beach, California’s experience piloting Connections to Care (C2C), a program designed to better connect people leaving the Long Beach municipal jail to social services in the community. Key features of the program were an embedded clinician in jail that provided release plans and referrals to services if needed and a graduate student fellow that coordinated transportation services, facilitated regular case-conferencing calls amongst local partners, and identified people eligible for homeless services. The program also benefited from the assistance of community health workers who typically shared lived experience of being incarcerated which helped them build rapport with C2C clients. The case study also highlights the unique challenges and potential solutions in facilitating a “warm handoff” when faced with a short window to make the connection. This case study provides lessons for other localities seeking to better coordinate services for people who frequently cycle in and out of jail, such as the importance of building local capacity to leverage county resources, having a “champion” in a local agency, and investing the necessary time to establish data-sharing agreements between key partners.