Participants will be able to: 1) Identify early indicators of student disengagement using behavioral and belonging-based data. 2) Analyze how identity, environment, and school systems impact student retention and experience. And, 3) Apply the CARE Cycle™ framework to improve student persistence, family trust, and long-term enrollment outcomes. Independent schools invest heavily in enrollment strategy, yet often overlook the most critical data point: student experience after enrollment. This session introduces a framework for interpreting student disengagement, identity tension, and belonging challenges as actionable data. Drawing from research on student-athletes in independent schools and leadership practice, participants will learn how to identify early signals, improve retention, and design environments where students persist and thrive.