Permanent supportive housing (PSH) is affordable housing paired with supportive services designed to enable residents, often those at risk of homelessness or who have serious mental illness or other disabilities, to live in the community and achieve long-term housing stability. Permanent supportive housing has been shown to improve the health of residents, many of whom experience complex health conditions, as well as reduce their health care costs. Funding for PSH, particularly for the supportive services they offer, is seriously threatened in Illinois. Medicaid funding is one option for funding supportive services that improve health outcomes for PSH residents, and new opportunities are arising that would make it easier for PSH providers to access Medicaid. Increasing access to Medicaid for supportive housing providers would not only help PSH providers keep their doors open, but would improve the health of some of the hardest-to-serve and most vulnerable healthcare consumers. This study uses surveys, interviews, and policy research to document barriers to accessing Medicaid for PSH providers, describe organizational capacities necessary to become a Medicaid biller, and provide lessons learned from PSH providers that have gone through the process of becoming certified to bill Medicaid. In addition, the report makes recommendations for changes to policy and practice that would expand access to Medicaid for PSH providers in Illinois.