Digital transformation has become a strategic agenda for educational institutions, including madrasahs, in responding to technological advancements and the growing demand for effective, efficient, and sustainable educational management. However, the implementation of digital transformation in madrasahs remains constrained by various organizational, technological, and human resource challenges. This study aims to analyze the challenges of digital transformation in madrasah management and to identify the adaptive strategies employed to support sustainable institutional development. A qualitative approach with a multiple-case study design was employed involving three Madrasah Aliyah in the Special Region of Yogyakarta, Indonesia. Data were collected through semi-structured interviews, non-participant observations, and document analysis, and were analyzed using thematic analysis following Braun and Clarke's framework. The findings reveal four major themes influencing digital transformation: digital transformation challenges, adaptive leadership and digital governance, organizational capacity building, and institutional innovation. The study indicates that successful digital transformation depends not only on technological infrastructure but also on adaptive leadership, collaborative organizational culture, continuous professional development, and integrated digital governance. Based on the cross-case analysis, this study proposes the Adaptive Digital Transformation Framework for Madrasah Management, which positions leadership, governance, organizational capacity, and organizational culture as interconnected capabilities supporting sustainable institutional transformation. The findings reinforce existing theories of digital transformation while extending them by incorporating the distinctive characteristics of Islamic educational institutions. The proposed framework offers both theoretical contributions to Islamic educational management and practical recommendations for policymakers and madrasah leaders in implementing sustainable digital transformation.