The purpose of our study was to enhance understanding of teachers' and principals' experiences and views regarding the high dropout rate in Norwegian upper secondary schools. Qualitative analysis showed that the teacher-student relationships over years had become more complicated since the implementation of a new educational reform, making the syllabus increasingly theoretical and thus reducing the practical value for many students. Limitations in students' knowledge, skills and academic interest, contributed to the creation of huge differences in academic levels within the class and thus reduced the quality of teaching. Societal changes were identified as possible factors underlying the high dropout rate. Better guidance regarding educational choices, study programs adapted to the students' interests, and actively nurturing involvement may prevent dropout.