The Affordable Care Act (ACA) of 2010 expanded access to health insurance coverage in the United States through online marketplaces that provided subsidized insurance coverage. Nonetheless, many obstacles made it difficult to enroll in and maintain ACA insurance coverage. In this article, we analyze obstacles to enrollment and continuous coverage based on an ethnography of ACA insurance enrollment in Rhode Island. We foreground consumers’ experiences and highlight the time and effort that people invested into getting covered. Unlike studies that focus on individual choices and employ a deficit perspective to understand gaps in coverage, this article argues that structural problems related to the organization of the American health insurance system, economic instability and bureaucratic eligibility criteria shaped the experiences of individuals and families seeking coverage. We found that people actively and intensely struggled to enroll and were met with multiple obstacles, most of which were beyond their control. In some cases, these obstacles resulted in gaps in coverage. In almost all cases, they created additional stress, were time consuming and frustrating. The most significant obstacles to enrolling in coverage were bureaucratic barriers, affordability, changes in personal or family status, and knowledge about health insurance and ACA program rules. We end by questioning the ethical basis of a health coverage system structured on ‘churn’ and offer policy recommendations to design programs that respect people’s time, avoid verification redundancies and are motivated by a mission to expand coverage.