The purpose of this study is to find key supports for educational leaders to provide for transgender educators to succeed in an educational workplace setting. By being and becoming aware of the issues involved and conceptualizing interventions to help transgender educators function at their full potential in the workplace, a school's leadership fosters social equity while also increasing the effectiveness of its organization. This paper draws from a mixed-methods case study that included a quantitative survey conducted with 27 transgender teachers and school principals and focuses on three qualitative in-depth cases. The results show that while some educational administrations support transgender educators in theory, they lack the proper tools to do so; alternatively, many other administrators remain openly hostile toward transgender educators, forcing some to find other work settings. For transgender educators of color, this task is more daunting because they face exponentially higher rates of violence and discrimination. To properly support and supervise transgender educators and principals, educational administrators must learn the necessary skills to provide a more welcoming environment for transgender educators, many of whom experience a myriad of personal struggles. These findings and the insights acquired have implications for transgender educators as well as state, district, and school administrators who wish to better support this growing segment of the LGBTQIA+ community.