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Though many states are moving to rapidly curtail discussions of race and LGBTQ+ rights in schools, Massachusetts stands in notable contrast, having just revised its standards for leadership preparation with a clear focus on preparing anti-racist school leaders. While this policy is critical to lay the intention for effective school leadership in the state, leadership preparation programs must attend carefully to the readiness of candidates to take on this work. Findings from this qualitative interview study with leadership candidates study reveal vast differences in candidates’ racial literacy (Rogers & Mosley, 2006; Sealey-Ruiz, 2011; Sealey-Ruiz & Greene, 2011), indicating the need for comprehensive and differentiated supports and learning prior to leadership work in the practicum and beyond.