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Increasingly, educators are positioned in the role of surveilling gender expression amid a nationwide flux of anti-LGBTQ+ legislation. This study explores the practice of critical reflection engaged by educators in graduate coursework related to an educator’s role in responding to and building relationships with LGBTQ+ identifying students. Critical Discourse Analysis and Freire’s notion of a reflexive praxis ground the study to examine the reflective writings of 39 educators. Findings demonstrate educators initially perceive compliance with policy and law as their only role. Through prolonged critical reflection, educators reveal types of thinking that propel shifts towards advocacy, affirming gender expression in schools. When shifts were not evident, fissures in thinking took shape, supporting a more humanizing role in relating to LGBTQ+ students.