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Caring teachers have been identified as a critical component of successful interventions with at-risk students, however just what constitutes a caring teacher is less well understood. Specifically, what are the behaviors, characteristics, and beliefs of caring teachers, and how are they impacted by the contexts within which they work? The purpose of this multiple case study was to understand more about caring teachers who work with at-risk students in secondary schools located in a Midwestern city and thereby to add complexity to the literature. Two middle school teachers and two high school teachers were recruited to participate. They were observed on multiple occasions and interviewed twice. The data from these observations and interviews were initially analyzed case by case; the cross case analysis based on the results from the individual case resulted in 6 themes that were present across the four cases. The following themes were identified: the role of relationships, perspective on at-risk students, providing opportunities for students to develop a positive sense of themselves, the value of a positive classroom experience for both students and teacher, negotiating power, and flexibility. Implications of this research for psychologists, educators, and policy makers, as well as future research are also discussed.