This paper presents a study of the engagement of active ageing users with social robots. Advanced digital technologies bring new challenges and opportunities for designers and users. The ways in which older generations interact with smart products deserve a closer examination. The purpose of this work is to develop insights and promote empathic reflections on active ageing users’ interaction with technology to inform the design of future smart products. Influenced by ontological realism and social constructionism, this research applies a Multimodal Extended User Research approach to unpack the social and emotional aspects of active ageing users’ experiences with new technologies. Three data collection stages included two rounds of interviews, a usability test, and an extended user experience of fifteen participants in their home environments. The study recommends designers to step away from the stereotyped views on active ageing users and recognises this user group as a knowledgeable and reflective demographic with ample expertise with disruptive technological changes. We argue that design practices need to account for social and subjective experiences rather than only focusing on users’ emotional ratings of the experience. Lastly, this research advocates for a critical analysis of companion technologies and recommends design practices to avoid generalising what “companionship” may mean to users.