This research explored the change management of integrating a Virtual Learning Environment (VLE) from a status quo to a Digital-based School Culture (DSC). A qualitative approach with a multi-case design was used to conduct research at three schools with various backgrounds. The schools, located in Indonesia, were at the same developmental stage and had a good practice of VLE integration. Data were collected through in-depth interviews with 30 respondents, participant observation and documentation research were also conducted on each case to obtain comprehensive and holistic data. The results showed seven stages of change management from status quo to DSC transformation. These stages include teams, resource preparation methods, vision alignment, digital skills development, obstacles, short-term reviews, and initiatives to boost technology acceptability. DSC transformation entailed developing digital modules, online and blended learning, and digitizing learning administration for improved decision-making. The finding serves as a valuable roadmap for DSC transformation practices to create systemic change strategies for pedagogical, technological, and organizational systems while considering school conditions.