The UCEM Virtual Learning Environment (VLE) is built on a Learning Management System called Moodle. Every few years, Moodle implements what is known as a Major Release. In early 2022 we learned that the next major upgrade from Version 3.11 to Version 4.0 would be occurring later that year. Release notes and information from Moodle made it clear this was a significant overhaul of the platform, aiming to improve navigation, accessibility, and overall user experience. We realised this upgrade would require more planning from the Learning Technology team than a typical VLE upgrade would.