We analyze how the interactions be-tween the trans population and the Chilean healthcare system shape specific processes of mal-aise associated with gender transition ("tran-sito de genero"). Adopting psychoanalytic and transfeminist conceptual approaches, as well as a biographical methodology, we examine autobi-ographical narratives of three trans subjects. We discuss three topics: childhood as a critical peri-od 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 gen-der transition. We show how politicization and the construction of an institutional framework, bodily aesthetical modifications, and the self-ad-ministration of medical knowledge emerge as some of the paths to navigate the gender transi-tion 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 psy-chopathologization 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.