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School leaders play a crucial role in the development of inclusive schools (Riehl, 2000) and have the potential to significantly influence transgender students’ school experience. Unfortunately, educational leaders do not typically receive training related to transgender youth or the laws that protect them (O’Malley & Capper, 2015). This paper reports data from 20 elementary-level school principals from six states. The findings provide rich descriptive stories of how principals supported transgender children but also the difficulties they experienced in shifting the larger school culture to decrease the emphasis on gender roles and create space for gender exploration.