This paper presents an initial study on how members of a 90-household large Danish permaculture community, Permatopia, would like an internal communication system to work regarding organization of work, distribution of natural and human resources, documentation of learning, and support for social sustainability. The study is informed by theory of permaculture: mainly the principle care for people and of theory from computer supported cooperative work (CSCW), in particular the phenomenon we-awareness. A combination of contextual inquiry and co-design methods were used to uncover community members’ needs, desires and concerns. Results show that a traditional app and profile-based communication system might not be beneficial to the social sustainability of the community. Instead, technologies and data should be handled with care: the benefits of structure and data visualization should be balanced with the need for privacy and respect for individual lifestyles, face-to-face communication and shared goals.