This paper looks at tensions arising in the educational thought of late antiquity from the conflict between assumptions regarding the low worth of practical knowledge and the contribution practical education can make to the wider purposes educational thinkers assigned to learning. Drawing on the educational writings of Augustine, Martianus Cappella and Boethius, I argue that there are vagaries and contradictions in their depreciation of the practical and a fuller, more hopeful, appreciation of the potential of practical education emerges. This assertion has contemporary significance due to the ancient binary's foundational and contemporary status as a tool of legitimation to reinforce the lower status of the practical and justify societal and economic determinants at the base of educational stratifications.