Interest in using Medicaid to address social determinants of health (SDoH) has grown in recent years, and practices to achieve this goal are still developing. We reviewed the most recently available state Medicaid managed care contracts for language on SDoH activities across 10 contractual domains. Based on our assessment of language pertaining to these domains, geographic diversity, and Medicaid expansion status we selected five states to focus upon in this case study: California, Colorado, Georgia, Illinois, and Pennsylvania. We interviewed Medicaid officials and Medicaid managed health plans across these five states in addition to community health centers, Primary Care Associations, and Community-Based Organizations. The main themes that emerged from these interviews are (1) Medicaid managed care contract language reflects an increasing, but still flexible, focus on SDoH that is in early stages; (2) The lack of direct Medicaid coverage of SDoH services requires providers to find alternative means of funding; (3) A delivery and/or financial model for integrating SDoH services could improve providers’ ability to meet patient needs; (4) Inconsistent SDoH screening tools limit data cohesiveness across organizations; (5) MCO and CHC relationships with local CBOs, though frequently informal, are critical to address SDoH; (6) the COVID-19 pandemic enhanced the need for strong relationships with local CBOs to meet increased patient demand; (7) Flexibility in approaches to financing and delivering SDoH services is useful at this stage. Despite a need for financing reforms that better incentivizes addressing patient whole health and wellness, the lack of clear standardization of SDoH screening tools, interoperable data collection systems, lack of robust health-related social services expenditure data, and financing uncertainties and insecurities present significant challenges for value-based payment arrangements.