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As part of the Digital Futures 2014, Annual Digital Economy All Hands Conference, we describe how BESiDE 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 contextual 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 care environments.