The information systems discipline is founded on the interplay between technical artefacts and their social and organisational contexts. Conveying this interplay is challenging in the classroom because the artefact is separated from its context, vendor material may limit teaching approaches, and students may perceive the benefits of an IS course in terms of technical training. This paper discusses these challenges with reference to three IS subjects, each using complex technological artefacts to convey learning outcomes. It opens a dialogue on design approaches to meet these challenges and enhance students’ understanding of the importance of a sociotechnical approach to their studies. These approaches take account of context, the expectations of external groups, the nature of the subject, and the characteristics of learners and teachers. The concepts of boundary crossing , boundary objects, and synergistic pedagogies, are suggested as ways of moving towards a comprehensive and integrated sociotechnical approach to business education.