At CHI ’13 (Extended Abstracts on Human Factors in Computing Systems), We describe BESiDE, a multi-disciplinary research project that investigates themes of ageing, wellbeing, and digital technologies within the context of built environment design. Focused on initial reflections from contemporary design practice we discuss that, design guidance; a lack of research ‘tools’ to engage with users; an absent research culture; and missing elements of design training, are factors preventing a designer’s holistic engagement with the experiences of older people and technologies within the built environment. We also present the continuing work and methods planned for assessing the user experience within older peoples’ care environments.