This case study takes an in-depth look at what type of students transition from elementary to middle school 21st Century Community Learning Center programs. Using binary logistic regressions, I identify key characteristics that predict whether or not a student will continue to attend the program after they transition to a new school and then discuss how to improve the attendance of after-school programs. Moreover, this case study also identifies how different school program environments serve different types of students in two cohorts starting in fifth grade. Middle school context moderates the effects of other variables that are predictive of participation in after-school programs during middle school. Thus, I demonstrate how understanding who makes successful transitions in the after-school program can help improve the sustainability and effectiveness of these programs.