Few technological innovations have caused as much controversy as Peer-to-Peer (P2P) file-sharing applications. Consumers have embraced it en masse, with the download figures breaking all time records for Internet application software. Content owners and some politicians have vehemently criticised the technology and its users, claiming that it merely offers a refined way of stealing intellectual property from creators. The paradox is that P2P both supports and conflicts with many of the policy regimes and goals related to the development of a knowledge-based society, Via studies of interactivity in different sectors (music file sharing, self-publishing and games), the paper focuses on the need to constantly reappraise policies, laws and principles if the long-term benefits of the Information Society are to be realised.