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This study explores how womanist caring manifests among K-12 school leaders. Helping to clarify what caring looks like in an education setting, womanist caring as a framework emphasizes relational engagement, political clarity, and an ethic of risk (Beauboeuf-Lafontant, 2002). In light of persistent racial and systemic inequities, this research examines whether and to what extent school leaders embody womanist caring in their practice. For leaders who demonstrate aspects of womanist caring, we analyze the organizational conditions that support or hinder such caring. We follow a qualitative design, drawing on interviews with 27 school leaders. The study provides insights as to what it looks like for school leaders to enact aspects of womanist caring and build capacity for caring in educational settings.