The purpose of this study is to comprehensively investigate the labeling phenomenon within high schools, considering the perspectives of school administrators, teachers, and students. The research employed a multiple-nested case design, focusing on two distinct school cases characterized by differences in student recruitment, teacher composition, and administrative staff. Participants were selected using a purposive sampling method, and data collection involved conducting semi-structured interviews with eight students, twelve teachers, and four school administrators. The data analysis proceeded in two stages: first, an independent analysis of each case, followed by cross-case analyses and comparisons between the cases. The findings of this research illuminate several key points. Firstly, labeling is prevalent among individuals within the school environment. Secondly, labels are formulated based on socially distinctive characteristics, which manifest within the organizational context. Lastly, labels applied to students possess the potential to trigger self-fulfilling prophecies.