This paper reports the findings of a research study on whether or not to structure reflective assessment tasks. It examines students’ perceived benefits or limitations from structuring reflective assessments in a Commerce WIL program at the University of Wollongong. Sixty-four students over two semesters responded to a questionnaire on their perceptions of structured reflective assessments in the Internship Program. The findings of the self-reported experiences were heterogeneous and indicative of the dominant themes relevancy and flexibility. We suggest these themes stem from a misalignment of assessment and reflective practice. Correcting this misalignment could be achieved by providing a balance of structured and unstructured reflective tasks. This study serves as an important reminder for WIL program administrators to examine their assessment strategy and decisions pertaining to structuring reflective assessments.