In this paper we chart the history of selected metaphors that have been used to describe Virtual Learning Environments (VLEs) over the last 15 years. Martin Weller famously claimed in 2007 that “the VLE is dead”. This provocation positioned the VLE as an object of history, forcing us to consider its past, present and future. This notion of historical mapping is important as many educational technologies that failed to deliver on their promises can be easily forgotten. Hence, we sought to develop a short history of VLE metaphors. Using a defined search and selection strategy we selected 30 metaphors spanning a 15-year period from 2004 to 2019 derived from a variety of sources ranging from social media to scholarly publications. We first arranged the metaphors according to a chronological timeline. Next we sought to unpack their significance by thematically analysing them using the notion of metaphorical concepts. Through this thematic analysis, six organizing metaphorical concepts were generated: Straitjacket, Behemoth, Digital Carpark, Safe Space, Smorgasbord and Pathfinder. We then used these metaphorical concepts as a lens, to map and explore historical developments and debates over the past two decades of educational technology. As the world scrambles to go online during the COVID-19 pandemic there has never been a more important time to remember and reflect upon digital learning history. Through this work we contribute to the history of educational technology by remembering its metaphors and what they have taught us. After we had navigated these historical seas, we noticed that the VLE was still here, as a limpet resolutely awaiting the next wave.