The idea of using digital technologies and in particular web 2.0 tools to enhance school collaboration has recently been received with great enthusiasm and a range of new collaborative initiatives has emerged. Through a comparative qualitative case study of four schools in the UK and Greece, this article analyses how online tools are supporting and facilitating school collaboration within the "eTwinning" programme--an EU initiative that seeks to promote web-based learning and collaboration between schools across Europe. In particular, it examines teachers' and students' compromised experiences of the tech-based eTwinning projects and highlights the factors that seemed to be undermining collaboration. It analyses whether the implementation of digital technologies for school collaboration has the potential to transform classroom practices or whether existing habits and "ways of doing" are brought into new contexts--leading to another case of "the old wine in new bottles" syndrome often attributed to the use of digital technology in education.