Based on interviews, focus groups, and observations for the duration of a 6-week high school summer enrichment program, this article considers the ways that having a visible trans faculty member shaped other teachers' understandings of and pedagogical approaches to the concept of gender. Using Judith Butler's concept of "losing expertise" in gender, the thematic analysis considers the ways that participants' notions of gender initially conformed to binaries and then, after working to support a trans colleague, shifted to more directly confront and critique gender norms in classroom instruction. Additional considerations are the degrees to which gender is inculcated into classroom spaces and the challenges that even veteran educators face in acknowledging and confronting gender normativity.