Principals and superintendents operating in high-choice environments are often faced with enrollment challenges as they compete for students. This case study examines the experience of a principal at Crossroads Elementary--a high-performing, culturally responsive, and innovative traditional public school that struggles to retain many of its older students. Despite outperforming most elementary schools in New York City and seemingly doing "everything right," most of their older students transferred to charter school networks as they approach middle school. We discuss implications in terms of equity, ethics, community engagement, and planning in high-choice districts.