This study aimed to discover the lived experiences of Dominican Mission School Administrators who administered the mission school of the Dominican Sisters of the Trinity in Region IX, Philippines, specifically their challenges and difficulties, their coping mechanisms, and insights on leadership. Utilizing qualitative-phenomenological design and purposive sampling approach, the researcher conducted an in-depth interview to 5 participants and focus group discussion with 7 participants. Data collection utilized a semi-structured validated interview guide. Thematic content analysis was employed as a data analysis tool. As revealed, Dominican Mission school administrators experienced the following difficulties and challenges as leaders: commitment in serving the mission, obligated to commit to the given-task, duty bound to make the right decision, relying on divine providence, challenges in teacher-retention, challenges in maintaining the school operation questioning competence and tasking and demanding. On the other hand, they were able to overcome these challenges through the following coping strategies: instill goodness in the community through mission, appreciate adversity, educating stakeholders, maintain good relationship, appreciate others, calibrate leadership style, improve oneself, inspire others, train faculty and staff, and teamwork. In addition, the insights shared by the study participants because of their experiences included flexibility in meeting the desired outcome, think strategically, identify and develop talent, practice participatory leadership, plan ahead, collaborate with stakeholders, set qualification standards in hiring personnel and ground work training is a necessity.