The phenomenon of shifting moral values among adolescents in the digital age demands a strategic role for Islamic boarding schools in character building, particularly in heterogeneous regions such as Sorong Regency, which faces specific sociocultural challenges. This study employs a descriptive qualitative approach with data collection techniques including participatory observation, in-depth interviews, and documentary analysis at the Darul Abror Islamic Boarding School. Key findings indicate that the boarding school director’s leadership strategy is implemented through the “asah-asih-asuh” approach, which integrates direct role modeling, persuasive personal guidance, and the enforcement of humane discipline. The contribution of this study lies in strengthening a contextual model of Islamic educational leadership for regions with high levels of diversity in Eastern Indonesia. The implications of this strategy are the creation of a boarding school ecosystem conducive to the internalization of the values of independence and religiosity among students through the figure of the leader as a surrogate parent. A brief discussion in this study highlights that the effectiveness of character building is highly dependent on the balance between managerial authority and the emotional closeness of the kiai. The study’s conclusion affirms that adaptive leadership grounded in nurturing, caring, and guiding principles can bridge the differences in students’ family backgrounds to foster outstanding character. As a recommendation, pesantren leaders should enhance the pedagogical competencies of dormitory supervisors and strengthen collaboration with parents to ensure the consistent and sustainable development of students’ character.
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