This document traces the evolution of learning management systems (LMS) and virtual learning environments (VLE) over time from the 1815s to 2010. It discusses how different technologies that were once seen as innovations, like paper, ink, and ballpoint pens, are now taken for granted. Similarly, the document outlines the journey of one educational institution in searching for an "iTopia" or ideal VLE, trying platforms like WebCT, OLS, Elgg, Ning, CollectiveX, Grou.ps, and Edmodo with varying degrees of success and failure. The key lessons are that digital learning is an ongoing process of experimentation in a "building zone" and there is no single perfect solution yet