This article has three purposes. First, it presents findings from a study of student retention and dropout in Cambodia, as pupils transition from primary to lower secondary school. Second, it aims to understand from an in-depth, emic perspective the dynamics of this process and the challenges that individual families and their students face around this transition. Third, it offers policy-relevant suggestions for addressing obstacles to students continuing in school. It meets these goals by combining complexity theory with the use of narrative research methods in interviews with student-parent pairs in urban, rural, and remote communities in Cambodia.