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A range of healthcare organizations in the US from Medicaid programs to health insurance companies to hospitals have expressed increased interest in addressing social determinants of health in the 21st century. One example of this is almost half of state Medicaid programs’ use of Section 1115 waivers to address beneficiaries’ social struggles, in particular homelessness. These waivers are intriguing because they involve not only referrals to but also direct payments for social services, employ healthcare organizations to provide social care, and expand Medicaid benefits amidst threats to the program. Drawing on primary documents and interviews with professionals from government agencies, health insurance companies, community-based organizations, and housing advocacy groups, I examine the strengths, tensions, and challenges of addressing housing insecurity through one waiver program in New Jersey. New Jersey’s Medicaid program, NJ FamilyCare, rolled out the Housing Supports Program (HSP) in 2025. The program calls on health insurance companies and community-based organizations to facilitate housing case management and funding for move-in and home remediation services. I find the program gives additional support to beneficiaries, and strengthens the social safety net by financially supporting community-based organizations and connecting them with NJ FamilyCare and insurance companies. On the other hand, professionals encountered tensions in distinguishing necessary versus wanted services, and the scope of their roles in healthcare versus social services. The program also suffers from complex documentation requirements and a complex structure comprised of many actors that reflects the fragmented, delegated, and privatized nature of the US social safety net. Further, program funding is limited and, regardless, does not address upstream drivers of housing insecurity. Amidst national concern about poverty, healthcare, and welfare, this study sheds light on the effectiveness and implications of broader attempts to address social ills via healthcare across the country.