Student mobility, the movement of students between schools, is a significant concern for schools and school districts because it is associated with negative outcomes for the individual students moving, the school experiencing mobility, and non-mobile students. In the Arroyo Independent School District (AISD), a pseudonym created to protect anonymity, almost 40% of students left the district at some point between fifth and 12th grade, and the exit percentage was highest following the first year of middle school. Analyses examining district administrative and achievement data highlighted exit patterns and timing but could not answer the district’s primary question: Why are families exiting after entering middle school? In this study, we explored this question using in-depth interviews with parents from 70 families with children enrolled in AISD middle schools—40 who remained in the district and 30 who exited—and a survey of parents in the district. This data allowed us to explore how parents perceive and experience district middle schools and consider what motivated exit.