Students regularly communicate using digital tools, yet many studies report difficulties with their use for undergraduate collaborative work and a detailed understanding of how students employ these tools for study purposes is lacking. This dissertation takes the student perspective, and investigates different digitally-mediated communication tools students used for studying, the activities this involved and their contextual influences. A wide-ranging literature review brings together cultural-historical activity theory with concepts from collaborative learning and dialogic communication theories, in which communication and collaboration are understood as mediated, multi-level activities, through discourse, action and system. Third-year undergraduates, working in special interest groups using personal and institutional communication tools, were the focus of the empirical setting. A partnership design, involving students as researchers, allowed for the collection of authentic communications data and in-depth, reflective, accounts. The findings show that although digital tools were part of the fabric of their lives and different tools were used, student communications in the groups were infrequent and lacked dialogic qualities. However, instant messaging conversations between existing friends frequently took place, involving mutual support and collaborative work. Communications were mediated by time, space and historical relations between participants, and required more or less collaborative effort. Tensions emerged as constraints on communications through task design, institutional regulations, ownership of tools, differences in purposes and the division of labour. This study concludes that cultural practices, institutional, pedagogical and interactional elements all contribute to constraining or supporting student engagement in communication and collaboration. Developing successful collaborative work therefore requires an in-depth understanding of these elements. Bringing students’ existing digitally-mediated practices into university work involves cultural change, with students acting as educational designers. The study further demonstrates how institutional rules, practices and processes influence students’ work. Further investigation within institutions and at policy level are urgently needed in order to improve student engagement.