Multiple studies have shown that transgender individuals routinely face increased levels of hostility and discrimination in the workplace compared to their cisgender peers; this is also true for transgender educators, who are often marginalized or silenced for expressing their gender diversity. Exploring the experiences of transgender teachers can provide much-needed information for school and district leaders seeking to support and affirm transgender individuals as valued members of the school community. The workplace experiences of six transgender educators in various teaching roles were examined in this qualitative study. The researchers utilized semistructured interviews to explore participants' professional lives, focusing on factors that affected decisions to reveal or conceal their gender identities, the climate of the schools in which they worked, and their support for LGBTQ students. Findings suggest that while support for LGBTQ teachers is growing, heteronormativity persists in troubling ways, particularly for transgender educators. Implications of these findings for school and district leaders are discussed.