In this paper, we describe a novel approach to the generation of reusable computer-based assets to support the production and customisation of learning materials for user and environment constrained learning scenarios. The approach is based on work carried out by the authors in knowledge base research, user modelling, training systems for industry, and learning environment development. Work is now under way on a project to develop both the technological solution and the pedagogic strategy necessary to produce an adaptive learning system based on this approach. The test vehicles for this project will be distance learning materials developed at Heriot-Watt University for Computer Science modules. Control information will be gathered from traditional classroom based teaching, and three different learning scenarios will be investigated. The outcomes of this investigation will be used to validate the approach, and provide information for the further development of the tool(s) and strategy thus developed.