A community-university team engaged low-income Hoosiers about their experiences with health and wellness and Indiana’s Medicaid expansion, the Healthy Indiana Plan (HIP). We present a Socioecological Model of the barriers and supports reported by HIP members as they navigate the program seeking good health outcomes. Top barriers include social factors of mistrust, stigma, and stress that compound access issues of transportation, food, and affordability. HIP members fare better with personal assistance in navigating their health coverage. Community partners increase members’ success by building trusting relationships and connecting members to add-on services that link health care access to social and environmental supports for wellness.