Despite increasing attention to the importance of caring in education, most research on caring in schools focuses on narrow dyadic relationships between individuals. The present study explores the processes used by school leaders as they strive to generate a culture of caring in schools. We find that leaders influence caring through the way in which they exemplify/enact their educational vision and personal values, but also through the adjustments they make to organizational priorities and structures. This analysis of leadership highlights the way that caring in schools transcends individual relationships and becomes an aspect of the organizational culture. The research and practice implications of the enablers and constraints on leaders' efforts to create a caring culture are discussed.