A growing number of studies have been addressing the use of technology in dementia care. As traditional views of society focus mostly on the symptomatic aspects of dementia, the use of technology is limited to people’s impairments. However, critical dementia aligned with the third wave of Human-Computer Interaction (HCI) adopted a more holistic approach that goes beyond individual cognitive functions. In this paper, I will (1) present findings about the experience of practitioners and family members of people with dementia (PwD) in a long-term care residence in Rio de Janeiro, Brazil; (2) Present and discuss digital design solutions for the well-being of PwD in the field of art therapy, Internet of Things (IoT), augmented technology and multisensory environment, and (3) Propose interaction qualities to solidify the epistemological shifts of HCI in the context of dementia care. The overall aim of this paper is to understand the psychological and social needs of PwD in the context of a long-term care institution and suggest a design approach that leads to digital artifacts that enhance engagement and social connectedness for the wellbeing of PwD.