We analyze how the interactions between the trans population and the Chilean healthcare system shape specific processes of malaise associated with gender transition (“tránsito de género”). Adopting psychoanalytic and transfeminist conceptual approaches, as well as a biographical methodology, we examine autobiographical narratives of three trans subjects. We discuss three topics: childhood as a critical period for gender transition and malaise; the role of institutions; and the ways through which subjects manage malaise. We argue that trans subjects face specific sociocultural conditions that lead to unique processes of malaise associated with gender transition. We show how politicization and the construction of an institutional framework, bodily aesthetical modifications, and the self-administration of medical knowledge emerge as some of the paths to navigate the gender transition process. Besides, we foreground the notion of “transitioning” (“transicionar”) by considering the criticism voiced by the participants. By using this notion, they interrogate the rigidity and psychopathologization of identity that is implicitly present in the notion of gender transition, as well as they enrich the transfeminist discourse in favor of their agency/autonomy.