Qualitative study conducted in 2014-2015 by researchers at the James Hutton Institute, Universita di Roma ‘La Sapienza’, Universitat Autonoma de Barcelona, and Oulu University of Applied Sciences, as part of the interdisciplinary research project Towards European Societal Sustainability (TESS) funded by the European Union’s Framework Programme 7. The analysis draws on the perspectives of 35 interviewees from five initiatives, situated in three European regions (Scotland, Rome, and Southern Finland). It aims to develop an understanding of community-based sustainability initiatives based on the initiative members’ own perspectives, with a particular focus on meanings of success and impact, experiences of development of their initiative, and situated relations within a wider societal context. The data collated point to the fact that the everyday politics of enacting a community initiative are characterised by plurality of perspective, negotiation, struggle and sometimes open contestation. Specifically, there seemed to be genuine tensions between differing aims and ambitions as attributed to the respective initiatives. Three types of tensions were identified: (a) divergences over the degree to which the initiatives should be political, (b) disputes over the extent to which rationalities of financial viability should take precedence over the original aims and (c) frictions arising from choices of organisational form and affiliation.