This position paper discusses different philosophical views of learning and the consequences of these different epistemologies on the design of online learning environments. Academic learning is proposed as a process of constructing knowledge and the development of reflexive awareness, where the individual is an active processor of information and is therefore proposed as a constructivist process. However, the pragmatic constraints of learning and teaching in Higher Education (HE) institutions pose clear restrictions on the use of pure constructivism. In fact, modularisation, semesterisation, accreditation needs, modes of assessment, as well as staff and financial limitations, mean that pure constructivist ideals are very difficult to implement and maintain at HE levels. Pedagogical models based on moderate constructivist approaches rooted and constrained by practice, may provide designers and educationalists with more useful and applicable approaches.