This qualitative study explores the lived experiences of school leaders at Rizal Memorial Colleges, Inc. with regard to teacher disengagement and attrition. Amid mounting worries about the sustainability and quality of education, the study investigates how these leaders perceive, respond to, and are influenced by the rising trend of teacher turnover. Through in-depth interviews and thematic analysis, the study reveals a complex interaction of emotional, organizational, and systemic factors that contribute to teacher disengagement, including workload stress, a lack of professional progress, insufficient support, and a misalignment of values. School administrators shared the emotional toll and practical challenges they encounter when attempting to maintain teaching quality and team morale during regular staffing changes. The findings highlight the critical need for responsive leadership, targeted retention initiatives, and structural improvements to promote teacher well-being and organizational stability. The study provides insights that can be used to inform policy, practice, and future research on educational leadership and teacher retention.