This study examines the experiences of six Nigerian migrants navigating healthcare systems amid unstable legal and bureaucratic contexts in Emilia-Romagna, Italy. Using narrative analysis informed by Geertz’s thick description, the research explores how structural inequalities, such as restrictive immigration policies, complex asylum processes, and fragmented healthcare services, intersect with cultural practices to shape access to care among participants in this study. Four key themes emerged: distrust of authorities, immovable structural barriers, the bootstraps narratives of self-reliance, and the bridging role of interpersonal connections. These findings illustrate how participants develop adaptive strategies in response to exclusionary systems, highlighting the need for policies that address both systemic inequities and the cultural resources that migrants mobilize to navigate bureaucratic barriers.