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This article seeks the role of the Kiai in the modernization of pesantren in Cianjur, West Java. Taking the cases of Pesantren al-Musyarrofah, Pesantren Darul Falah, Pesantren as-Syuja’i, and Pesantren Darussuada al-Amin, this research uses qualitative methods. The study found that although these Pesantrens played a significant role in da’wah, education, and the development of socio-religious institutions in Cianjur, their existence of experienced ups and downs due to the management system practiced by the pesantren leadership. In addition, it was also implied that modern management combined with the Kiai charisma has become a success factor in the modernization of the pesantren. Abstrak: Artikel ini berupaya mengkaji peran kiai dalam modernisasi pesantren di Cianjur, Jawa Barat. Dengan memokuskan pada kasus Pesantren al-Musyarrofah, Pesantren Darul Falah, Pesantren as-Syuja’i dan Pesantren Darussuada al-Amin, penelitian ini menggunakan metode kualitatif. Berdasarkan penelitian yang dilakukan ditemukan fakta bahwa meskipun berperan besar dalam bidang dakwah, pendidikan, dan pengembangan pranata sosial keagamaan di Cianjur, keberadaan keempat pesantren mengalami pasang surut yang disebabkan oleh sistem manajemen yang dipraktikan oleh pimpinan pesantren. Penelitian ini juga mengimplikasikan bahwa manajemen modern yang dipadukan dengan kharisma Kiai menjadi faktor keberhasilan modernisasi pesantren. Keywords: Islamic education, pesantren, kiai, management, leadership

RETHINKING THE ROLE OF KIAI LEADERSHIP IN MODERNIZING PESANTREN IN CIANJUR, WEST JAVA