Listening to students’ voices might result in the design of more effective learning practices, assuming that learning and teaching can be attuned more adequately in those practices. Therefore, research was carried out to investigate the characteristics of successful innovative learning practices using Web 2.0 technologies to establish to what extent they might serve as a model for learning practices in more or less similar contexts. Five learning practices were investigated through a range of processes including document analysis and by interviewing students. Additionally, a cross case analysis was carried out to track down success factors of teaching and learning with Web 2.0 technologies, and to find out to what extent these practices are contextual. The analysis showed the importance of co-production and co-creation in learning practices supported by the use of Web 2.0 technologies, and the crucial role of students’ motivation and teacher’s willingness to experiment with new learning practices.