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Learning Management Systems (LMS) have increasingly become essential software in K-12 and post-secondary institutions. In April 2022, University (Name Redacted) in Canada announced transitioning its university wide LMS from Sakai to D2L’s Brightspace. This research explores how University instructors across various departments experienced transitioning LMS. It highlights successes and challenges encountered by the university instructors throughout the transition. Both quantitative and qualitative data were collected through an online survey administered to instructors. Additionally, a one-hour semi-structured interview was conducted with the two project managers who led the transition. Results show varied levels of satisfaction with the LMS transition process among university instructors. Findings highlight the importance of technical support, pedagogical support, and ongoing professional development to ensure smooth transition.