With the emergence of Web 2.0 (Blog, Wiki, RSS, YouTube, Flickr, Podcast, Social Networks, and Mashups), new ways of communicating, interacting and being on the Web have arisen. These new communication tools and strategies can radically change some specific work processes in communities, such as the work processes of an autarchy. Some authors emphasize the advantages of using Web 2.0 tools in autarchies; thus, we were interested in exploring the possibilities and constraints of implementing these tools in our region of Portugal, the Minho. Using a case study methodology, we aimed to find out about the possibilities of implementing Web 2.0 tools in autarchies through exploring the interest and motivation of autarchic collaborators in their use (our unit of analysis in autarchies). Information was gathered with the help of a questionnaire, the design of which was based on previous exploratory interviews and applied to four autarchic units in the Minho region. In each unit, three different target-groups were surveyed (Councilors, Information Systems (IS) Technicians, and General Staff), so that we could triangulate the data. Data analysis and results emphasized the interest and motivation of the autarchies in using Web 2.0 tools, as well as the main constraints that would be faced during Web 2.0 implementation. It also allowed us to establish some guidelines for adequate Web 2.0 implementation, including an “ideal” profile of the person responsible for the implementation process.