In light of the innumerable changes in post-secondary environments that reflect a movement toward inclusive education and a reliance on real-world evaluations in the form of field placements, we report on our findings from a collaborative research project that examines field placement experiences from a variety of perspectives. Our research project, prompted by our own observations of the barriers to equity for field placement students with disabilities at our institution, is an attempt to reflect on our disability service and our teaching and learning practices. We expanded on the traditional focus in the field by creating a multi-dimensional cross-sector collaboration and by including the perspectives of Professional Program Directors, Field Placement Coordinators, and students with disabilities. We found that all stakeholders reported barriers to success in field placement for students with disabilities, saw few solutions, and anticipated the barriers to continue into the world of employment. We discuss these findings in relation to the implications for teaching and learning and for disability service provision in post-secondary institutions.