Background: In higher education (HE) settings, staff and students are often end-users of a variety of educational technologies, tools and platforms, including Learning Management Systems (LMSs). As technological evolution is constant, transitioning to a new system may be a familiar occurrence. For technology to support educational purpose more fully, further insight needs to be gained into how staff and students actually experience the process of transition. This article focuses on this area in the context of institution-wide transition to a new LMS. Purpose: The study's aim was to explore how academic teaching staff and students experienced a university-wide technological change process: namely, a process of changing to a new LMS. Method: Data were collected through a series of interviews with staff who were involved in the first stage of the change process. In addition, students enrolled in the first tranche of subjects undergoing transition participated in surveys. Data were analysed using a qualitative, comparative analysis approach; student and staff perspectives were compared, and the points of intersections and divergences between the viewpoints were located. Finding: Detailed analysis helped identify factors that contributed to a smooth transition, while also showing how staff expectations of student behaviours and needs were not always aligned with students' own approaches to technology-assisted teaching and learning, which tended to be predominantly pragmatic. Conclusions: Feedback gleaned from investigating stakeholders' transition experiences can contribute in a valuable way to informing change processes and support empowering change. The findings highlight how positioning LMS transition as a student-centred and education-led process, rather than as a large-scale technology project, has potential to support staff and students to have a positive and relatively seamless transition experience.