The purpose of this study is to examine how youths in alternative educational settings view caring relationships with their teachers. In this study caring relationships with teachers are viewed as a factor contributing to the resilience of youths. Youths themselves are considered to be “at-promise” of academic success rather than “at-risk” of failure (David, 2008; Davis, 1996; Franklin, 2000; Whiting, 2006). Caring relationships between youth “at-promise” and teachers are approached as a system of interrelated components, and viewed through the lens of of the ecological systems theory, as proposed by Brofenbrenner (1979). The study reveals youths’ perceptions of caring in teacher-student relationships which are grouped into main three themes including activities, principles, and environments. The impact of gender on youths’ perceptions of caring is examined. This qualitative research is rooted in the interpretivist paradigm and utilizes the constructivist grounded theory method, as described by Charmaz (2000, 2006). Data collection took the form of semi-structured interviews with eleven youth from an alternative educational setting in the urban area of Saskatchewan. The implications for teachers, schools and teacher education programs are discussed, and possible directions for enhancement of practices are suggested. The avenues for future research are explored.