Background/Context: In Ontario, and Canada more broadly, anti-discrimination on the basis of gender identity and gender expression is enshrined in the Ontario Human Rights Code and the Canadian Charter of Rights and Freedoms, which have required schools to address trans inclusion. However, the ways in which educators understand or enact these policies, and whether they are even aware of them, remain largely underexplored. Purpose/Research Question/Focus of Study: Our purpose was to learn more about educators’ awareness and understanding of trans-inclusive policies in schools and the extent to which such policies were informing practice. Participants: While this research is based on survey data comprising 1,194 respondents, this article examines comments provided about trans-affirmative policy from 463 educators. Research Design: This study involves large-scale survey research conducted on 1,194 educators in Ontario K–12 schools; the survey was disseminated via social media and educational affiliates. We draw primarily on the qualitative data component of the survey, where educators provided detailed comments about and insights into trans-inclusive policies. We employed a reflexive approach to coding and thematic analysis to identify key themes. Findings/Results: Although our quantitative data depicted a favorable assessment of support for trans-affirmative policies—94% of respondents found their school’s policy to be very or somewhat relevant—our findings highlight a discrepancy between policy and practice, and a lack of commitment to addressing cisgenderist, cisnormative, and cissexist systems. The themes that emerged from our coding and analysis of the qualitative data were: (1) educators’ understanding of policy as accommodation; (2) individualized approaches to trans inclusion; (3) lack of administrative support and intervention; (4) the gap between policy and practice; (5) transphobic and cissexist resistance to supporting gender diversity; (6) the need for trans-affirming and gender-expansive curriculum, and (7) the problem of generalized approaches to equity and acceptance of diversity. In addition, we discuss several educator comments that raise important questions about race and the need for intersectional approaches to addressing equity and trans inclusion in schools. Conclusions/Recommendations: We advocate for a paradigm shift with respect to the necessity of employing a trans epistemological framework that addresses the need for gender-expansive education which focuses on the harmful effects of cisgenderism, cisnormativity, and cissexism in the education system. Central to addressing gender justice and trans marginalization in schools for all students, we conclude, is the need for policy makers to ensure accountability and budgetary allocation for the provision of resources and professional development for educators in schools.