Collaborative work among students, while an important topic of inquiry, needs further treatment as we still lack the knowledge regarding obstacles that students face, the strategies they apply, and the relations among personal and group aspects. This article presents a diary study of 54 master’s students conducting group projects across four semesters. A total of 332 diary entries were analysed using the C5 model of collaboration that incorporates elements of communication, contribution, coordination, cooperation and collaboration. Quantitative and qualitative analyses show how these elements relate to one another for students working on collaborative projects. It was found that face-to-face communication related positively with satisfaction and group dynamics, whereas online chat correlated positively with feedback and closing the gap. Managing scope was perceived to be the most common challenge. The findings suggest the varying affordances and drawbacks of different methods of communication, collaborative work styles and the strategies of group members.