Service learning and problem-based learning (PBL) are distinct, yet related educational approaches. When collaborative learning events which encourage the application of the PBL principles to real world challenges faced by Not-For-Profit organizations (NFPs), these learning approaches become potentially synergistic. However, there is limited research exploring expectations and experiences of NFP stakeholders and students involved in such events. By interviewing a sample of stakeholders in relation to an experiential NFP-focused workshop initiative, it was revealed that while tangible benefits were identified by both parties, opportunities exist to optimize the design, management, marketing and learning benefits of future initiatives. These opportunities centre on closer collaboration with NFPs to clarify and manage expectations, as well as encouraging practicality and applicability in ideas generation. This research provides insights into the challenges and benefits of the service learning/PBL interface when directed towards the NFP sector.