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In recent years, public figures have inundated the national education discourse with calls to limit certain critical conversations in K-12 classrooms, including conversations on race and racism. This is a critical issue leaders should address, as it directly impacts if and what young people learn about the history of racism in the US and how racism permeates and emerges in modern society. While, clearly, some decision makers would like to eliminate these conversations altogether, it is less clear how teachers view engaging students around these issues. This paper employs Milner’s (2012) Opportunity Gaps Explanatory Framework to analyze data from the Teachers and Race Talk Survey pertaining to teachers’ perspectives on factors influencing their decisions to engage or not engage their students in critical conversations on race in their classrooms. The findings have implications for how universities train teachers and how education leaders create environments within schools to facilitate critical examinations of the impact of racism on our society.