A qualitative study was undertaken that explored the conditions for transformative learning in cooperative education as a form of work-integrated learning (WIL), towards the development of a theoretical model. Four case studies were analyzed based on interviews with WIL students, supervisors and their co-op coordinator. The findings revealed that the enablers most involved in contributing to transformative learning were: opportunities for work and learning, a supportive environment, student capabilities, co-workers, supervisors, and assessment and reflection practices. Furthermore, the integration of these transformative outcomes into the WIL academic program or workplace was dependent upon the time and value given to transformative processes, institutional requirements and a positive emotional environment. The implications of these findings are that WIL theoretical models include considerations of: perspective, socio-cultural context, dialectic and mediated processes, time and creating a positive emotional space to support the critical reflection necessary for transformative learning outcomes. Furthermore, adopting a view of WIL as an interaction between two systems opens up possibilities for innovation and renewal in our WIL programs and workplaces.