The development of VR technology for healthcare requires not only technical development but an understanding of the context in which the technology will be used, the people involved, and the environment, practices and processes in which it will be placed. In this chapter, the authors describe insights gained on this subject from the evolution of visualisation software for stroke rehabilitation through a series of RCUK-funded projects. The chapter discusses the value of qualitative design methods in engaging with users to both inform the technical development process and evaluate its outcomes, how they can be effectively integrated and the particular practical challenges involved in applying this approach in healthcare. The argument is made for using a methodology which endeavours to understand how to design and evaluate healthcare interventions which meet the needs of the current healthcare context and all its users and stakeholders, and which acknowledges that successful rehabilitation involves social processes that can be difficult to explore using quantitative methods alone.