This document summarizes efforts to advocate for Medicaid coverage of case management services for individuals experiencing chronic homelessness in Massachusetts. It describes two pilot projects that collected data showing improved housing and health outcomes for individuals receiving case management. Key stakeholders cultivated relationships and presented the data to state officials, advocating for Medicaid to cover case management. Their efforts have led to expanded coverage of these services for more individuals. The document recommends other communities collect similar data and develop partnerships to pursue Medicaid coverage of case management for the chronically homeless.