Technology (such as touchscreen tablets) is increasingly used to enable people in residential care homes to engage in personally meaningful activities and occupations. Residents in these facilities are recognized to have reduced opportunity to engage in activities of their choice, which were previously part of their lives. The aim of the study that forms the basis of this case study was to explore the experience of staff and residents of residential care facilities, using iPads as a medium to engage in meaningful activities and occupations. This case study describes key facilitators and challenges to conducting research with multiple stakeholders, along with the strategies used the study team to maximize rigor and effectiveness. It also focuses on the practical issues which impact on engagement with multiple stakeholders, as experienced by the study team. Overall, the challenges posed by this methodology are outweighed by the potential benefits of producing relevant and applicable research findings related to the use of these interventions in practice.