Research on the experiences of trans youth has generally emphasized their disparate risk for negative educational, housing, and health outcomes. While drawing attention to very real vulnerabilities, these depictions can represent trans youth as one-dimensional passive victims. Some recent research draws on resiliency theory and offers a strengths-based perspective highlighting the strategies trans youth employ and the resources they draw upon in the face of challenging circumstances. In this study, we look to the concept of situated agency as a way to understand how risk and resilience simultaneously characterize the high school experiences of trans youth. Through hearing their own accounts of daily life in a large urban public school district, we seek to understand their attitudes, behavior, and choices as strategies for coping, surviving and resisting the bureaucratic structures that create conflict by upholding traditional binary gender norms. In so doing, we seek to redirect the spotlight on the practices and systems that constrain trans youth agency--rather than the trans youth, themselves--as the most appropriate focus for intervention.