Purpose - In the era of rapid digital transformation, madrasah principals are required not only to possess strong leadership skills but also to demonstrate digital literacy in managing schools and guiding the educational community. This study aims to develop a digital e-book on madrasah principal leadership rooted in the cultural values of pesantren, intended to foster digital literacy among students and school stakeholders. Methods - Employing a research and development (R&D) approach with the ADDIE model, the e-book was validated by material experts, media experts, and practitioners. Findings – The validation results revealed high feasibility scores: 90.1% from material experts, 89.2% from media experts, and 91.5% from practitioners, with an overall average of 90.26%, categorized as "very feasible." In terms of practicality, student users rated the e-book at 81.48%, indicating a "very practical" category, particularly in aspects such as ease of use, cognitive content, and information presentation. The e-book integrates pesantren values such as sincerity, discipline, and community-based leadership into digital learning, providing a culturally grounded yet technologically relevant tool. Research implications / limitations - This research offers practical implications for the development of educational media that aligns with Islamic educational culture, though further studies are needed to assess long-term impacts on leadership behavior and digital competence in diverse school contexts. Originality/Value - This study presents an innovative blend of pesantren-based leadership education and digital literacy training through an interactive e-book, addressing a gap in culturally contextualized digital resources for Islamic educational institutions.