This study analyzes the transformation of kiai authority in pesantren governance, particularly the shift from personal-charismatic toward collective-collegial leadership, and its implications for institutional sustainability, scholarly traditions, and student character formation. The study was conducted at Pesantren Annuqayah, Guluk-Guluk, Sumenep, comprising 19 branch areas under one foundation. Using a qualitative descriptive case study design, data were collected through observation, semi-structured interviews with masyayikh and pesantren community members, and document analysis. Data were analyzed using the interactive model of Miles, Huberman, and Saldaña through data condensation, display, and conclusion drawing and verification. The findings show that the transformation did not eliminate charismatic leadership but reconfigured authority within a collective governance structure. Initially, authority centered on the kiai, whose legitimacy was rooted in personal spirituality and charisma. Increasing institutional complexity encouraged the establishment of the Dewan Masyayikh, strengthening collective-collegial leadership. This model synthesizes spiritual charisma and managerial rationality, preserving moral legitimacy and scholarly traditions while strengthening governance, institutional continuity, and students’ moral character formation.
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