More and more organisations are using projects as a means of managing their business; increasingly, ‘new initiatives’ are the focus of organisational life. Such initiatives could include cultural change programmes, organisation redesigns, or process improvements. Tackling the sociological and psychological aspects of the project is a great enough challenge, but there is often a requirement to develop a technological dimension too. Accelerating technical advancements brings an extra level of complexity to the projects so that, in general, projects have become more complex—not only do they tend to have a wider variety of customers to satisfy, but they also tend to utilise more sophisticated technology and have more far-reaching implications than ever before. It is not too surprising that some projects ‘fail’; the increased complexity of projects brings an obvious rise in the associated risks. However, the increased complexity of projects also brings a rise in the opportunities for learning through the management of knowledge therein. These are opportunities that are not being fully exploited at present, as illustrated by the continuation of the ‘failure-to-learn’ and ‘learning-to-fail’ themes in the literature (e.g., Lyytinen & Robey, 1999; Cannon & Edmondson, 2004); a more active stance would consciously draw lessons from projects, from ‘successes’ and ‘failures’ alike. Parallel to the growing emphasis on projects in organisational life and their changing nature, there is growing recognition of the interplay between the fields of project management (PM) and knowledge management (KM). Reference has already been made to the opportunities for more effectively managing knowledge within a project setting. This article operates at a finer level of detail and draws attention to the potential synergy between project teams and a much popularised social network derived from the KM arena—that of communities of practice (CoP). In doing so, the disciplines of PM and KM are explicitly bridged and, it is put forward, the prospect of breaking the ‘learning-to fail’ and ‘failing-to learn’ loops is raised.