In this article, we provide theoretically informed empirical insights into administrative and pedagogical approaches to supporting transgender students in schools which rely on a fundamental rationality of individualisation and rights. We draw on trans epistemological frameworks and political theories that address the limits of liberal individualism to provide insights into how transgender inclusion and recognition are conceived and enacted in one particular school in Ontario. Our case study contributes to an emerging body of research that documents the viewpoints of educators in response to the increasing visibility of trans youth in schools and a growing awareness of their experiences which have highlighted the institutional and systemic barriers continuing to impact on the provision of support for transgender students in the education system. Overall, the case study serves as an illustrative exemplification of the problematic of trans inclusion when it is driven by a logics of liberal individualism and rights that fail to address broader forces of cisnormativity and cisgenderism.