In 2022, the City of Denver launched the Housing to Health Pay for Success project. The project provides supportive housing to people experiencing chronic homelessness and high rates of arrest and who are at high risk for avoidable and high-cost health services paid for through Medicaid. This early implementation brief provides an overview of the first 18 months of implementation, from July 2022 to December 2023, during which the Housing to Health project focused on outreach and enrolling eligible participants into permanent supportive housing. Findings from early project implementation reveal the Housing to Health project has built the foundations required for future results, including strong outreach, quality supportive housing and services, intentional navigation of the criminal legal and health care systems, and promising housing retention. Future reports will analyze the project’s long-term impact on housing stability, days in jail, and health care utilization and cost.