Background: For decades, Black students have been more likely to be suspended than their White peers despite any evidence suggesting they are more likely to misbehave. This research builds on critical race theory and social justice leadership to explore and contextualize leadership practice as it relates to the racial discipline gap. Purpose: The purpose of this article is to understand how race and school context contribute to the ways principals enact discipline. Findings: Our study highlights the manner in which principals serve as key disciplinary decision makers, advocates, and intermediaries between districts, teachers, students, and families. Overall, some principals described enacting what could be called harsh punishment in the name of neutrality, consistency, and/or racial bias, while others described resisting institutional racism, challenging the status quo, and engaging in disciplinary approaches that address antecedents to misconduct and teach students about their behavior. Conclusion: These findings suggest that principal preparation programs must support students in identifying and exploring the systematic racism operating broadly in their districts and locally in their schools.