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The purpose of this paper is to briefly consider elements of transphobia in middle schools that are currently at play in Ontario, Canada and can, as a starting point, be reduced significantly with inclusive leadership from principals. The topic is being further investigated by me as an exploratory case study that is part of my doctoral studies. I initially explain the negative and troubling situations for transgender students in schools then turn to considering principals’ leadership in terms of the imperative to lead and change schools so that they become affirming and responsive to the needs of trans students. I then draw some conclusions that highlight key priorities for improving principals’ leadership and trans student’ school lives.