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In the last several decades, an increasing number of individuals in the U.S. now identify as transgender, gender fluid, or gender queer, broadly grouped under the umbrella category of “trans.” Gender scholars have argued that we may be moving away from a man/woman binary towards a cis/trans binary. In this context, “detransitioning” has become central to political debates about gender non-conformity. Detransitioning is the practice of pausing, stopping, or reversing a previous gender transition. Those who detransition find themselves in the middle of the emerging cis/trans binary—weaponized by anti-trans groups to deny the legitimacy of trans identities, criticized as transphobic by parts of the queer community. In this paper, I ask: How do narratives of detransitioning shape the emerging cis/trans binary? To answer this question, I use computational grounded theory to carry out a media analysis of articles discussing detransitioning. I argue that medicalization, or the lens through which gender non-conformity is understood as a medical problem to be treated, shapes public detransitioning narratives and helps maintain the legitimacy of a binary categorization system. This project contributes to the literature on recent changes to the U.S. gender binary by exploring the role of medicalization in the maintenance of binary categorical logics. More broadly, it speaks to the mechanisms through which categorical systems maintain legitimacy in the face of changing demographics and labels.