Nowadays universities expand their role of serving an engine of transformational sustainability towards delivering the Sustainable Development Goals in local community. Despite the fact that there are best practices of “sustainability university–community partnerships” already presented worldwide, a number of both internal (organizational) and external (community driven) challenges have been described for sustainability-based university outreach efforts. This paper provides a state-of-the-art overview of corresponding best cases and challenges, estimating their relevance to the case of Uppsala University Campus Gotland. Mapping sustainability related initiatives on Gotland, the only island-based region of Sweden, has been organized in a form of 30 in-depth interviews with local societal actors (non-for-profit organizations, businesses, regional authorities, individual projects), as well as representatives of seven Bachelor and Master study programs at the Campus Gotland in August-November 2020. The mapping results highlighted key challenges in terms of “common language” between different actors around sustainability issues, non-formal communication prevalence, moderate openness to newly established organizations, lack of university outreach initiatives and locally based practically oriented research organized by Campus Gotland for societal actors. At the same time, many perspectives and unique strengths were identified, such as tight and complex societal connections on the island, high local commitment for making Gotland a pilot sustainability-driven region in Sweden, similar views on key local sustainability related problems and challenges. Based on mapping results, the paper presents a sustainability initiatives open source database formed on in-depth interviews, as well as official statements of organizations and multi stakeholder local projects currently existing on Gotland.