New York City (NYC) is considered to be one of the world's most progressive cities and gender and sexuality diversity (GSD)-inclusive education departmental policies appear to reflect these values. However, even within such a context, NYC educators report challenges in their work to meet the needs of trans/gender-diverse students and the visibility of trans/gender diversity more generally within their pre-K-12 school communities. This paper reports on interview data from 31 school staff members from nine public and independent schools located in the NYC metro region, with a specific focus on their framing of inclusivity and bullying, and reported support of trans/gender-diverse students. Based on educators' representations of their schools, the nine schooling environments fell into two broad clusters: (1) those framing trans/gender inclusivity as an anti-bullying initiative and working at the minimum policy requirements, and (2) those working beyond bullying discourses and policy frameworks to conceptualise trans/gender inclusivity as integral to the school's mission and as offering clear whole-community benefit. Findings support the constraints of bullying discourse on even supportive educators' curricular 'translation' of GSD-inclusive policies, reinforcing the need for relevant policy reframing and targeted of professional development opportunities, particularly for school leaders.