The issues and experiences of work-integrated learning (WIL), accounting, and financial planning academics across higher educational institutions in developing innovative WIL programs are the focuses of this study. The authors reflect on their responsibilities and goals, centering on how these aligned with student and institutional expectations for both work-based situations and classroom-based simulations. Cross-institutional collaboration on WIL approaches in undergraduate and postgraduate accounting courses reveal contrasting priorities and tensions, when addressing the needs of stakeholders. Particularly noticeable are the institutional requirements for a technology-driven WIL curriculum that meets with student, industry, and institutional expectations. This research provides insights about educator preparedness for delivering technology enhanced WIL programs, and an in-depth analysis of academic engagement with WIL designs. Drawing on activity theory, to analyze the constraints and confluences perceived in the design and teaching of WIL programs, this research contributes to the understanding of effective ways to manage this activity.