States and policymakers have expressed a strong interest in using Medicaid to address social determinants of health (SDOH). While this approach holds promise for improving outcomes and reducing costs, using Medicaid to pay for services outside the medical system creates challenges. This article examines efforts to address SDOH in Oregon, which, as part of its 2012 Medicaid waiver, incorporated health-related services that lacked billing or encounter codes and were not included in Oregon's Medicaid state plan as a strategy to improve outcomes and control costs. We examine the varieties of health-related services that were used and describe the specific challenges in deploying and paying for these services. We conclude with lessons from Oregon that can help states and the federal government as they work to address SDOH.