Transfer of learning can be demonstrated by assessment tasks mirroring real life situations. This can be attempted in real organisations, or by simulating the real, life experience in a structured case study. In this paper we discuss experiences with work situated learning and difficulties that commonly arise. The alternative of encapsulating real life experience in hypermedia based materials is then presented using a number of case studies. Finally a model is presented for producing these “real life” encapsulations which overcomes the problems of lack of structure in individual experience without losing the advantages of common lifelike experiences. Some testing of the model is presented. The model involves the steps of: • Determine real life skills commonly required • Imagine a context rich enough (and having the case study design team with enough knowledge of the context that they can draw from their experience to fill in the holes) • Structure (partition) the case so that team work is possible without too much overlap between tasks. Identify the overlapping points that will force the level of teamwork between students that is intended • Identify parts of the solution development where students can be synchronised using a published solution to part of the problem • Create answers for each skill point starting from the top • Tag each part of the answer with the essential component of information required for an answer • Determine the most likely format that the tagged information would be found in real life • Create the set of tagged information using unskilled labour to provide detailed data • Write the project brief so that an appropriate level of guidance is given for navigating the information sources