Virtual learning environments (VLEs) and managed learning environments (MLEs) are emerging as popular and useful tools in a variety of educational contexts. Since the late 1990s a number of ‘off-the-shelf’ solutions have been produced. These have generally been targeted at the tertiary education sector. In the early years of the new millennium, we have seen increased interest in VLEs/MLEs in the primary and secondary education sectors. In this chapter, a brief overview of e-learning in the secondary and tertiary education sectors over the period from 1994 to 2004 is provided, leading to the more recent emergence of VLEs and MLEs. Three models of e-learning are explored. Examples of solutions from around the world are considered in light of these definitions. Through the case of one school’s journey towards an e-learning strategy, we look at the decisions and dilemmas facing schools and school authorities in developing their own VLE/MLE solutions.