Enhancing academic standards and assessment practices in work integrated learning (WIL) is crucial to securing its place in high quality student learning. Yet, the diverse purposes and perspectives associated with WIL present distinctive challenges to achieving this goal. The paper highlights the issues involved and explores them through a case study from student work placement in urban and regional planning. The study was funded by the Australian Learning and Teaching Council. The project team comprised members from RMIT University, Griffith University and La Trobe University. Whilst the study focused on one particular industry, the paper explores implications that are transferable to other disciplines and professions. In particular, it seeks to acknowledge the complexity of both the learning outcomes of work placement and the contexts within which that learning occurs.