The charismatic leadership of kiai plays an important role in shaping organizational communication within Islamic boarding schools (pesantren). Its influence extends beyond formal authority to include moral exemplarity, spiritual legitimacy, and religious practices that foster collective solidarity. This study aims to analyze the role of charismatic kiai leadership in developing vertical, horizontal, and diagonal communication at Pondok Pesantren Ibnu Kholdun Al Hasyimi in Widoropayung, Besuki, Situbondo, Indonesia. The study employed a qualitative approach with a case study design. Data were collected through interviews, participant observation, and documentation, and analyzed through data condensation, data display, and conclusion drawing and verification. The findings indicate that vertical communication is shaped by exemplary conduct, respectful language, and decision-making that combines deliberation with spiritual considerations. Horizontal communication is supported by the Islamic principle of ta’awun (mutual assistance), deliberation, and collective solidarity, which strengthen cooperation among organizational members. Meanwhile, diagonal communication develops through open interactions across hierarchical boundaries, inter-unit coordination, and the involvement of alumni and the surrounding community. Religious practices also contribute to maintaining shared values and social bonds within the pesantren community. However, reliance on the kiai as the central decision-maker and communication intermediary may limit organizational autonomy. This study highlights the importance of integrating spiritually grounded leadership with formal communication systems to support the sustainability of organizational communication in Islamic boarding schools
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