Proponents of cooperative and work-integrated education embed critical reflection in their programs to enhance the likelihood of an experience resulting in meaningful learning for students. Theoretically framed guidelines in the literature on how to determine and facilitate critical reflection in practice remains very limited, highlighting the importance of developing ways of improving stakeholders understanding and practice of critical reflection within these complex learning arrangements. Data analysis of a qualitative case study exploring critical reflection in a specific cooperative education context enabled the development and design of a transactional model to illustrate the positioning and functionality of critical reflection. The theoretical underpinnings for this model are derived from John Dewey’s educational writings. To date no published diagrammatic representations have been found to assist with the development and enhancement of our understanding of the complex dynamics and interplay of factors that influence and contribute to the practice of critical reflection, and the consequences of these transactions.