Lack of access to affordable and stable housing has been a growing crisis in the USA. The Department of Housing and Urban Development (HUD) has identified housing as a social determinant of health. Medicaid has been identified as a potential vehicle to reduce homelessness, but, historically, federal Medicaid funding could not be used to pay rent costs. Federal funding could be applied to other housing supports, such as a search for housing, and some states have funded limited rent support programs for Medicaid enrollees with state or local funding. Recently, some states were granted waivers that allow federal Medicaid funds to be used for 6 months of rent support in certain populations with high social need, and other states have submitted similar waivers. These experimental waivers raise the important question: Should Medicaid be used to pay rent costs for individuals in whom homelessness affects health? The authors review the major arguments for and against the use of federal Medicaid funding to pay for direct housing costs by presenting the “Pro” position and the “Con” position to this debate.