In this paper we describe the design of a reminiscence-based social interaction tool, namely Collegamenti, that aims at stimulating conversations and a sense of mutual awareness in residential care. Unlike previous work, Collegamenti focuses on stimulating the different types of relationships that are relevant to the quality of life in residential care: interactions with primary family caregivers, contacts with the larger family, friendships with peer residents and interactions with the nursing home staff. We explore the needs and challenges of this scenario in terms of social interactions but also in terms of how to make the technology sustainable and well integrated with care practices and initiatives, and report on the findings from the qualitative studies and concept validation.