This paper examines how parent advocacy and teacher allyship played an important role in supporting six-year-old Violet Addley's (a pseudonym) gender transition in elementary school. We first met the Addley family in the spring of 2015 when we interviewed them for a research study on the experiences of lesbian, gay, bisexual, transgender, and queer (LGBTQ) families in Ontario schools. The goals of the study are to interview LGBTQ families about issues that come up at school, document how families have worked with schools to create safer and more respectful classrooms for their children, and share the families' interviews with teachers and principals so they can begin to think about the ways they can best work with LGBTQ parents and their children. Our paper also discusses what a group of teachers learned about parent advocacy and teacher allyship from their engagement with the Addley family interviews.