In this paper, I discuss how high school English teachers at private, college preparatory schools approach conversations about race and ethnicity in their classrooms. Using twelve interviews with high school English teachers across six schools in the Chicagoland area, I find that their engagement with themes of race and ethnicity is predominantly shaped by school context. Specifically, schools that were more committed to racial justice and teaching students about race led to student bodies who were more receptive to talking about race, and teachers therefore felt more empowered to facilitate these conversations. These findings demonstrate that administrative- level support and interventions help cultivate environments to talk about race in honest, productive ways. For the most part, schools that included standardized college prep curricula, such as Advanced Placement (AP) or International Baccalaureate (IB) classes, did not prevent teachers from building diverse syllabi. While many of the teachers spoke of positive experiences regarding teaching about race, respondents highlighted ongoing challenges, such as choosing which narratives to showcase, creating safe spaces for all students, and difficulty getting students to critically think about race. The findings presented here give insight into how race is being taught in private school settings where the student body is predominantly white and affluent, helping policymakers better understand when approaches to teaching about race and ethnicity are likely to be successful for this demographic.