This study aims to explore strategies for strengthening digital leadership in private vocational school (SMK) principals in facing the challenges of digital transformation in the era of education 4.0. The approach used is qualitative with a multi-site case study method. Data were collected through in-depth interviews, participatory observation, and documentation at private vocational schools in Bogor Regency, West Java. The results of the study show that effective digital leadership is characterized by technological competence, digital vision, and managerial ability in integrating technology into learning and school governance. Strengthening strategies are carried out through ongoing training, collaboration with the digital industry, and the development of an organizational culture that is adaptive to technology. The implications of these findings provide strategic recommendations for policy makers and vocational education managers in supporting digital leadership capabilities systematically and sustainably.