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Based on Bronfenbrenner’s Process-Person-Context-Time model, this study explored the attitudes and potential factors affecting children’s educational participation in two non-governmental organization-sponsored rural schools in Siem Reap, Cambodia. Focus groups and individual interviews were conducted with students (female and male), teachers, principals, and parents. A discovery-oriented qualitative analytical approach revealed that at the individual level, truancy and student respect for school regulations impacted school participation. At the family level, parental support and family difficulties influenced school participation. At the school level, teacher ability, teacher-parent interactions, and adequate resources either facilitated or hindered student success. At the socio-cultural level, socioeconomic conditions, communal supports, and traditional gendered expectations created gender disparities in school involvement. Policy implications include a nation-wide comprehensive professional development program targeting teacher training (structural level), a strong teacher-counselor partnership to facilitate the development of literacy campaigns (community level), and increasing female mentors and counselors to increase gender parity (cultural level).