Abstract: This study explores how school leaders in the Philippine education system respond to poverty, disasters, and chronic crises in the context of reform initiatives like the Basic Education Sector Reform Agenda (BESRA). Through qualitative analysis of narratives from school leaders, it examines the challenges they face and their responses to these challenges. Two main leadership responses are identified: custodian leadership, focusing on maintaining the status quo amidst structural challenges, and crisis leadership, dealing with chronic crises like annual flooding. The study reveals a disconnect between national reform policies and local realities, leading to cynicism among school leaders. Despite efforts to promote equity, challenges such as resource shortages and policy inadequacies persist. The findings emphasize the importance of context-specific solutions and meaningful engagement of school leaders in policy development. Addressing these issues is crucial for building a more resilient and equitable education system in the Philippines. Keywords: School leadership, Philippine education system, Poverty, Disasters, Chronic crises