The study aimed to explore the challenges students face in their transition from middle to high school and the effect of these challenges on them in a private high school in the context of Chitral. This school is situated in a rural area of Pakistan, where students from various middle schools get admission after passing their grade-eight exam. A case study design within qualitative research methodology was employed to explore the transitional challenges and their effects on students during their transition from middle to high school. Overall, the sample consisted of twelve students, ten parents, four teachers and three school principals. The data were gathered through observations of the school activities, interviews of principals and teachers, focused group discussion with parents and students and document analysis. The results of the study highlighted some of the academic and social challenges and their effects on students during their transition from middle to high school. The common academic challenges include high homework load, parental and teachers' expectations of high grades, high number of monthly tests, lack of subject specialist teachers, and lack of individualized attention by teachers. Social challenges faced by students were lack of English speaking culture in middle schools hampering relationship formation, lack of peers' support during transition, cultural norms and low sporting facilities hampering relationships, and cold attitude of middle school principals towards students. The study also found that transitional challenges had both positive and negative effects on students' social and academic performance. From the results of the study it also appeared that students do not receive adequate academic and social support in middle schools, which hinders their smooth transition to high school. The findings also revealed that intervention programmes in high school include strict rules, co-curricular activities and academic support such as extra classes and co-teaching practices, which does help to an extent, yet these intervention programmes were not sufficient to ameliorate the ailments of transitional challenges. According to the results of the study, parental support came in the form of their help in homework, provision of financial assistance and emotional guidance, having high expectations of their children, and volunteering. The study also found that students mostly use emotion focused coping strategies (procrastination, avoiding social relationships, divine support, and teachers help) as compared to problem focused coping strategies (proper scheduling, more time to studies, and organization). The study also concluded that long journeys due to distance hindered both academic