Web 2.0 technologies are becoming more popular in the everyday lives of students. As a result, teachers and designers have begun to explore their use in formal education. This paper presents evaluation findings from a collective case study of six Web 2.0 implementations in Australian higher education. The research was undertaken as part of a larger study that sought to understand how today’s students use information and communication technologies to support their learning. Conducted across three universities, the research included a range of disciplines, class sizes and year levels. A common evalu- ation strategy was used in order to collect comparable data from which commonalities and differences could be identified. This paper provides an overview of the study, describes the methodology used, summarises the implementation experiences of staff and students involved and presents the key find- ings. The results suggest that most students had little prior experience with relevant technologies and that many struggled to see the value of using Web 2.0 technologies for learning and teaching, both of which have important implications for the design of appropriate learning tasks. While the argument can be made for improving the design through better task-technology alignment, this study also highlights inherent tensions between Web 2.0 and educational practices.