This thesis examines the complex relationship and ongoing tensions between the transgender community and the official medical systems in both the People’s Republic of China (PRC) and the Republic of China (Taiwan, ROC), focusing on how these interactions unfold within a shared Sinophone cultural framework. Transgenderism remains a relatively marginal topic within East Asian Studies. Existing scholarly understandings are often shaped by frameworks rooted in North Atlantic, Eurocentric, and Anglophone institutions. This research investigates how cultural and political environments in China and Taiwan shape the lived experiences of transgender individuals, and conversely, how trans subjectivity and embodied practices influence the development and operation of medical institutions. Drawing on interviews with 25 transgender individuals and three healthcare providers across China and Taiwan, alongside ethnographic fieldwork conducted in both community and a hospital in Beijing, this study argues that the medical system, characterized by state-medicine and body-oriented logic plays a central role in structuring the relationship between the state (embodied by medical institutions) and the trans community. Furthermore, the underrecognition of psychological illness (Kleinman 1988) shapes both clinical interactions and institutional protocols. They are also shaped by the historical legacies of biopolitical paternalism and authoritarian governance (Ma 2020), functioning as mediating forces that seek to maintain social harmony between trans individuals, their families, and the broader public. Overall, this research contributes to anthropological discussions surrounding the medicalization of transgender identities in modern Sinophone societies. It offers a culturally grounded analysis of how discipline, classification, and institutional discourse configure gendered embodiment in China and Taiwan.