This study explores the major challenges that affect students' enrollment and participation and the key measures schools take to mitigate the challenge and help students continue their education. The data were collected from 23 secondary school grade nine students in Amahara Regional State in Ethiopia using the structured questionnaires from students and teachers as well as by using semi-structured interview from school principals. The results suggest that the major challenges were family related (opportunity cost of students, family issue such as parental conflict, taking care of family members) factors and associated with individual characteristics of students (disability, illness) are prominent ones. The study also made clear that though the effect size is very small, there is a statistically significant difference between urban and rural students in the reasons for their drop out from school. This study also highlights that schools do not facilitate conditions for poor children to be supported by NGOs or exempt them from school fees. They also do not provide food and health services for poor children. In addition, schools have no guidance and counseling or social worker who can support students when they face problems in schools. Moreover, though schools have no corporal punishment policies and procedures, schools implement other punishment techniques such as to miss class if they arrive late.