This study examines how stress management enhances the managerial behavior of principals leading public Tsanawiyah madrasahs (MTsN) in Riau Islands Province, an archipelagic setting where geographic dispersion, accreditation pressure, and rapid digitalization intensify occupational strain on madrasah leaders. Using a qualitative descriptive design within a naturalistic field-research paradigm, data were gathered through participant observation, structured interviews, and documentary review across three purposively selected sites—MTs Negeri 1 Batam, MTs Negeri Tanjungpinang, and MTs Negeri Bintan—with principals, vice-principals, teachers, and administrative staff as key informants. Data were analyzed using the interactive model of collection, reduction, display, and conclusion drawing, with credibility secured through prolonged engagement, persistent observation, and source triangulation. Findings show that principals who master five stress-management competencies—recognizing stress sources, regulating emotion, solving problems, adapting to context, and sustaining life balance—translate these competencies into stronger planning, organizing, actuating, controlling, and decision-making behavior. Persistent obstacles include sudden policy shifts, heavy administrative loads, limited human resources, and island logistics. The study offers a cross-island, qualitative account of stress management as a functional managerial resource, with implications for the Ministry of Religious Affairs, madrasah leadership training, and future comparative research.