While health care-associated financial burdens among uninsured individuals are well described, few studies have systematically characterized the array of financial and logistical complications faced by insured individuals with low household incomes. In this mixed methods paper, we conducted 6 focus groups with a total of 55 residents and analyzed programmatic administrative records to characterize the specific financial and logistic barriers faced by residents living in public housing in East and Central Harlem, New York City (NYC). Participants included individuals who enrolled in a municipal community health worker (CHW) program designed to close equity gaps in health and social outcomes. Dedicated health advocates (HAs) were explicitly paired with CHWs to provide health insurance and health care navigational assistance. We describe the needs of 150 residents with reported financial barriers to care, as well as the navigational and advocacy strategies taken by HAs to address them. Finally, we outline state-level policy recommendations to help ameliorate the problems experienced by participants. The model of paired CHW–HAs may be helpful in addressing financial barriers for insured populations with low household income and reducing health disparities in other communities.