This study examines the kyai leadership model based on pesantren culture amid the challenges of digital transformation. The central problem revolves around how kyai sustain the authentic values of pesantren including religiosity, discipline, moral exemplarity, and communal solidarity while navigating rapid technological change and global cultural pressures. This research employs a qualitative library research approach, systematically drawing on books, peer-reviewed journals, and scientific articles relevant to pesantren leadership and Islamic educational management published predominantly within the last decade. The findings reveal that kyai leadership functions through an integrative model that harmonizes, traditional pesantren culture such as manners, independence, orderliness, and devotion with modern management principles, digital literacy, and formal curriculum development. Crucially, this integration preserves institutional identity while enabling pesantren to remain educationally competitive and socially responsive in contemporary Indonesia.