The future of schools and schooling constitutes one of the major areas of current education debate, especially in light of the increasing importance of digital technologies in contemporary society. While having undoubted educational potential, these digital technologies mark a significant area of uncertainty, which are encapsulated in current debates over the place of so-called “Web 2.0” technologies in education. This chapter offers a critical perspective on the emergence of Web 2.0 applications and the hype surrounding their uptake in education. It chapter looks at the changes brought about by Web 2.0 in society, the opportunities that schools might benefit from and, sadly, how little use teachers are making of these opportunities. It concludes by arguing for the need to retain a realistic, if not critical, perspective on schools and Web 2.0 – seeking to find ways of using Web 2.0 technologies to work with the schools of today, rather than against them.