Context: A growing body of work reflects the ways in which gender-creative and transgender students are ill-served by current social climates in the vast majority of public schools. Few studies have explored this topic from an educator's perspective. Purpose: This study was designed to develop a conception of the barriers and supports that exist for educators working to create learning environments that affirm transgender and gender-creative students. Participants: Twenty-six Canadian educators who all had direct experience working with gender-creative and transgender students in school settings with an average of 10 years' experience in schools and mean age of 43. Research Design: This project is a Social Action Research (SAR) project designed to identify what are common challenges and why these challenges are present. Data Collection and Analysis: Each educator was interviewed for 60-120 minutes using a flexible interview guide and audio recordings were transcribed for analysis. Data analysis was conducted via an ongoing and exploratory design. We also performed a cross-case analysis to compare experiences and perceptions across teachers in elementary and secondary schools as well as alternative and traditional schools. Findings: We identified barriers and supports experienced by our participants. Barriers included: (1) the pervasiveness of transphobia; (2) high frequency of school transfers; (3) the propensity for gay and lesbian educators to take on an "expert" role; (4) ethnocentrism; (5) relying on a 'pedagogy of exposure' and using certain students as "sacrificial lambs;" (6) the overlapping challenges of working with youth who also have behavioral and learning difficulties; and (7) the balancing act required to navigate complex issues with little training and support. Supports identified were: (1) alternative schools as sites of refuge and spaces where transgender and gender-creative students are reportedly thriving; (2) empowered transgender and gender-creative students; (3) vigilant and protective adults; and (4) best practices. Recommendations: In order to address systemic barriers we advocate for an application of principles and best practices aligned with critical, queer, and anti-oppressive pedagogies. We recommend that schools: (1) develop a more student-centered, flexible curriculum; (2) promote interdisciplinary and project-based learning; (3) model and promote creativity; (4) establish restorative justice programs; (5) reduce or entirely remove sex-segregated activities and spaces; (6) integrate discussions of gender diversity as a social justice issue throughout the curriculum.