This qualitative case study aimed to explore at-risk high school students’ perceptions of a supportive caring learning environment. There is a body of research that indicates that students’ perception of a learning environment they deem to be supportive and caring promotes their sense of belongingness and commitment to learning which may in turn improve their academic achievement. Although an abundance of evidence supports the value of including students’ as essential partners in developing the learning environment, rarely have students been invited as experts to contribute to the knowledge base regarding the fit between learner and environment. As such, this study honored the statements of at-risk high school students in a small alternative high school and thoroughly examined their perceptions of a supportive caring learning environment. A combination of research methods and techniques such as participant observation, informal conversations, interviewing, tape recordings, student surveys and questionnaires were employed to obtain the data. The results show that students define supportive and caring learning environments as those in which their administrators, teachers, and others adults in the school deliberately and intentionally provide them with support in and out of the classroom. In addition, the study revealed that at-risk high school students perform at higher levels socially, emotionally, and academically when they perceive that they are in a supportive caring learning environment and regarded as respected members of the school community.