General Background These schools must maintain a balance between deep religious understanding and openness to change. Specific Background This study explores the role of Kiai leadership in strengthening student moderation attitudes at Pondok Pesantren Hayatul Islam Sunan Drajat, Probolinggo Regency. Knowledge Gap Previous literature lacks explicit focus on connecting specific Kiai leadership patterns with the reinforcement of student religious moderation using a localized case study approach. Aims This study aims to explore the role of Kiai leadership in strengthening student moderation attitudes at Pondok Pesantren Hayatul Islam Sunan Drajat, Probolinggo Regency. Results The results of the research show that the Kiai plays a central role in the formulation of work plans, the development of educational programs, and the character building of students, while student moderation is evident through socio-religious activities and holistic teaching. Novelty The integration of comprehensive administrative work plan formulations with personal exemplary modeling under a centralized Kiai leadership model establishes a structured framework for religious moderation. Implications These findings provide new insights into the relationship between Kiai leadership and the strengthening of student moderation attitudes, as well as offering a leadership model that can be applied in other Islamic boarding schools. Highlights: The Kiai plays a central role in formulating work plans, developing educational programs, and directing student character building. Student moderation attitudes are manifested in daily life through socio-religious activities, routine discussions, and holistic teaching. Direct personal modeling and supervision by the Kiai effectively balance religious tradition with openness to contemporary developments. Ketwords: Islamic Boarding School, Student Character, Religious Moderation, Kiai Leadership, Character Development