Presently, a variety of policies are being updated, proposed, and/or passed related to gender in the school system, including anti-LGBTQ+ legislation at the state-level and updated regulations to Title IX at the federal-level. These policy debates are steeped in polarized political issues such as the scope of sexual harassment and the rights of LGBTQ+ students. However, educational policies are often disconnected from the day-to-day experiences of students and rely on the limiting notion that pursuing justice for one group must simultaneously oppress another. Thus, there is a need to holistically describe the lived experiences of students in the school system to understand how school policies and practices impact students across multiple gender groups. This critical ethnography describes the culture and context of gender in the New Orleans public charter school system by eliciting the lived experiences of cisgender girls, cisgender boys, and students with complex gender identities (e.g., transgender, nonbinary, etc.) in individual and group interviews. In-depth document analysis, interviews with school professionals, and observations further contextualized these student experiences within the structural-level forces that sustain inequality. Grounded in critical social work theory, intersectionality, queer theory, and transgender theories, this study critiques power, investigates the nuanced intersections of multiple axes of oppression, undermines essentialist identity constructions, and honors lived experiences. Data analysis revealed three major themes: the reproduction of cisheteropatriarchy, formal school regulation, and activism and resistance. Structural gender oppression was distinct, but interrelated based on the gender identity of students and this oppression was deeply intertwined with race in schools. Further, the culture and context of gender in schools was shaped by students, school staff, and the school as an institution and emerged as a complex and nuanced force in schools, at times conforming to the limiting demands of cisheteropatriarchy and contributing to gender inequity, and at other times, acting as a powerful counter-measure. Building on this complex narrative, implications for policy, practice, and social work education are considered. Despite internal and external threats to gender equity in schools, social workers must be prepared to courageously work towards gender equity and resist perpetuating cisheteropatriarchy.