This paper focuses on the difficulties of assessing multi-year team projects, in which a team of students drawn from all three years of a full-time degree course works on a problem with and for a real-life organization. Although potential solutions to the problem of assessing team projects may be context-dependent, we believe that discussing these in our paper will allow readers to relate to their teaching cases and increase the general appreciation of team project related work. Findings discussed in this paper are based on the first cycle of action research in relation to an existing multi-year team project scheme. Based on the interpretivist perspective, this work draws on data from staff and student focus groups, semi structured interviews and surveys. Team project clients were also asked to comment on their experiences and the way they would like team projects to be improved in the future. Since issues affecting the success of team projects are quite closely inter-related, a systemic view is adopted rather than analysis of a single issue in isolation. Overall there is a feeling that multi-year team projects are a good idea in theory but can be challenging to implement in practice. It is argued that the main areas of concern are the assessment process, the dilemmas and tensions that it can introduce, and the related inconsistencies in stakeholder involvement, which can compromise the learning experience if not handled well. We believe that the assessment process holds the key to a successful learning experience in team project work. (Contains 2 tables and 2 figures.)