Fuelled by the increasing connectivity afforded by the Internet and the flexibility offered by Web technologies, the use of technology in education has become increasingly common. However, despite claims that the Web will revolutionise education, many attempts at Web-based education simply reinforce current ‘poor’ teaching practices or present more of the same disguised in updated packaging. We argue that this occurs because of differing pedagogical assumptions and a limited understanding of how flexible learning differs from traditional approaches. In particular, we argue that flexible learning demands an increased focus on constructivism and the sociological aspects of teaching and learning. This chapter presents two frameworks that situate our approach to flexible learning with respect to more traditional offerings and discusses the implications for educational technology design.