This phenomenological study intends to reveal and understand the leadership resiliency of eight school heads managing multigrade education in Langilan District, Division of Davao del Norte. Purposive sampling was employed in selecting the participants, and ethical considerations were addressed while gathering the data from them through in-depth interviews and thematic analysis. Results revealed the experiences, ways of coping, and insights in terms of leadership resiliency in managing multigrade education. Issues spanning from constraints in school resources, adjustments in leadership philosophy, issues in curriculum management, teacher burnout and turnover, and challenge of parents’ involvement have brought difficulties among the serving school heads. Despite this, the school heads were never stopped in their tracks to understand the needs of the learners and make efforts to improve the achievement of learning outcomes in their schools. In response, school heads prioritized self-case and work-life balance. They also sought support and linkages with the stakeholders, while demonstrating flexibility and resilience as a leader. They also collaborated and provided support for the teachers. Above all, they remained optimistic amidst challenges. With these experiences gathered, the school heads learned leadership resilience from their experiences. They also learned about the needs of their schools, which include the allocation of more resources to multigrade schools. They also reflected on the importance of stakeholders in school leadership. Profoundly, they realized that leading a multigrade school is a chance for them to empower the community. Generally, the findings suggest the inspiring stories of school heads in serving remote multigrade schools as well as the learners herein who are fighting to attain quality education. Thus, the findings call for relevant agencies and educational leaders to provide more support to the school heads, teachers, and learners in multigrade schools to ensure the delivery of quality service and education to underserved communities.