Digital transformation is reshaping how Islamic boarding schools (pesantren) organize administration, learning, communication, and stakeholder services. This study primarily employed a qualitative approach within a convergent mixed-method design to examine how two pesantren respond to digital change, identify its effects on institutional governance, and formulate a value-based model for digital transformation. Qualitative data were obtained through interviews, participatory observations, and document analysis, while quantitative data from a structured questionnaire administered to 30 students were used to support and triangulate the qualitative findings. The analysis revealed an adaptive-selective strategy: technology is adopted when it aligns with institutional values, provides practical benefits, and presents manageable risks. Digitalization improves administrative efficiency, access to learning resources, communication with parents, transparency, and public trust, while face-to-face Qur'anic transmission, bandongan, sorogan, and character formation remain central. Key challenges include unequal digital literacy, infrastructure and maintenance costs, data-security risks, inappropriate content, and fragmented systems. Based on these two institutional cases, the study proposes an Adaptive-Conservative Model for Digital Transformation in Pesantren, consisting of value foundations, governance transformation, learning innovation, and ecosystem strengthening. The model is context-specific and requires broader empirical testing before wider application.