Universities across Australasia regularly evaluate their Learning Management Systems (LMS) to meet the increasing digital teaching and learning demands. LMS reviews conducted approximately every five years or so are driven by factors such as pandemics, contract renewals, fiscal considerations, and the pursuit of optimal student online learning experiences. Recent trends show that Australian universities are conducting LMS reviews more frequently and transitioning to new LMSs at an accelerated pace (Phil, 2022; Sankey, 2023a). This is to ensure the LMS of choice meets the Next Generation Digital Learning Environment (NGDLE) functionality (Educause, 2018), is affordable, reliable and is still fit for purpose. While ongoing LMS reviews are common, there is a lack of published information on how higher education institutions undertake them. There was little available to unpack how best to engage in open, transparent, and aspirational conversation with staff and students about their experience with the LMS. As part of the review, even less was published about the dialogue on the future teaching and learning needs and the future of the LMS. To help address this gap in the literature, this practice-based paper reports on our approach and the steps taken to propose a unique two-phase / multi-stage model for reviewing an LMS and offers a useful checklist for those who may want some help getting started.