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In the last few years, transyouth have recounted to courts their experiences of discrimination by administrators who were either following policy or extrapolating transphobic practices from unstable interpretation of policy (Doe v. Regional School Unit 26, 2014, Whitaker v. Kenosha School District, 2018, among others). Transyouth have recounted being interrupted in their studies, repeatedly being misgendered, and, threatened with official forms of “outing,” often by school personnel. This paper explores the tensions inherent in being invited into such districts to do trainings on transgender issues when the (d)evolving district policy seems intent on excluding transgender youth. There is a certain sense of futility in training a district where an administrator taunted a transboy in a boys’ room to “come out and use the urinal, if you’re such a man” on best practices of including trans students, including providing them with space to come out in schools if they feel unsafe at home (Riley, 2018), only to find district administrators developing anti-trans policies. The district now requires mandatory reporting to the principal and the parents of any trans student who requests recognition from a school professional, based on conservative Family Policy Council advice (Hasson, 2013). When trainings encourage recognition and respect and policies require notification to administrators who are among those whose actions have created the conditions whereby training was part of a legal agreement, educators are left feeling more torn than ever. While trans youth who are supported by their families suffer almost none of the negative outcomes unsupported transyouth experience (Olson, Durwood, & McLaughlin, 2018), those without supportive parents are at risk for negative outcomes, in schools and beyond. LGBTQ youth are 2.2 times more likely to be homeless because they have been rejected by their families (Morton, Dworsky, Patel, & Samuels, 2018). As confused as teachers may be, trying to sort out their commitment to ethical practices or to following district rules, trans students are ever more pushed back into the closet.