This exploratory case study aimed at investigating the stakeholders' perceptions of student dropout during middle and secondary classes. The stakeholders included parents, head teacher, teachers, and dropped out students, and their views were collected for this study. The study was also aimed at exploring the actions of the school management in improving the situation. The study conducted in a government boy's secondary school of a less privileged context. The study aimed to understand the contextual circumstances that led to students' dropout. The sample collected was of students who had dropped out of school in the last three years. In addition, the school identified some students at-risk, who were interviewed as probable dropouts. They were also considered as part of the sample, albeit of a different category. The stakeholders were interviewed in order to locate what factors actually contributed to the dropping out of students. The findings of the study confirm previous studies. Some of the factors contributing to student dropout are socio-economic, academic performance of the students, and repeating the class as a result of failures in examinations. Another factor was peer pressure and low value of education both from parents as well as students. This study also brought out some other interesting factors like school policies that allow students choices to stay away from classes and only appear in examinations, lack of any remedial support to students facing difficulties to cope with the academic demands, and an uninviting school environment. Another factor that was considered both by parents and students was the local environment in which the school was located that was neither very conducive nor safe for students to access school.