Policy makers are increasingly attentive to the importance of supportive school climates, even as many students report that schools seem to be uncaring places. Using recent scholarship that foregrounds the organizational and contextual dimensions of educational caring and student engagement, we use qualitative case study interview data to examine these concepts in two schools. We find that organizational and contextual factors such as students’ sense of continuity and the manner and degree of staff collaboration have important implications for caring, student engagement, and school climate writ broadly. Implications for policy makers and education leaders are discussed.