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Using a longitudinal cross-case design, this study asked 17 graduates of an urban teacher preparation program over time to describe conceptions and practices of caring in a high-poverty school and what influenced those practices. The teachers varied significantly in how they viewed their teaching context and, consequently, their academic and behavioral expectations, use of students’ cultural practices and languages, connections with parents; and level of advocacy on behalf of students. Program supports for culturally responsive critical caring included program mentors and instructors, field experiences in high poverty schools, and course content that disrupted previous thinking about caring. Non-program supports included family values/models, caring roles in volunteer work and employment, and administrators and colleagues who modeled culturally responsive caring.