Enterprise2.0 is the use of emergent social software tools to improve knowledge sharing and collaboration within and between firms, their customers and partners. This paper proposes that Enterprise2.0 is a double‑edged sword and should be adopted cautiously. Emerging trends in e‑business are specialisation and collaboration, creating a diverse population of organisations, each tightly defined by its core competences, interacting in a constant sequence of transient relationships, each motivated by a particular market opportunity. These dynamic business networks depend on the establishment of appropriate platforms and global standards to enable smooth interaction between the service components, in particular, appropriate metadata such as ontologies. The dynamism of such an interconnected yet free‑ wheeling economy is constrained unless risks relating to investment in a new business relationship are reduced to levels where the risk‑reward ratio favours agility rather than inertia. For its advocates, Enterprise2.0 techniques promise to contribute to the evolution of dynamic, agile, collaborative e‑commerce. However, its egalitarian and permissive nature creates challenges. Folksonomies allow a more customer‑centric view of an organisation's value proposition but may also undermine carefully devised official ontologies. Collaborative filtering may provide a mechanism for mitigating risk but the trust created is dependent upon the perceived credibility of the reviewers. A high profile example of an initiative designed to facilitate dynamic e‑commerce which failed due to unsatisfactory classification of its members and the perceived risk of interacting with unknown reputations is examined. Recent academic research and practical applications that address these conflicts are reviewed.