The growing role of technology in society has led to calls for more experiential, community-engaged learning to equip students with the skills and qualities needed for developing technology for the public interest. Yet, despite the growing number of initiatives that seek to provide such experiences, there is still limited research on the barriers that make it challenging to do so, particularly from the perspective of community members not currently engaged in campus partnerships, but interested in doing so. To better understand these challenges, we ran a matchmaking program to help community members connect with potential campus partners and conducted a series of interviews with 8 community stakeholders (nonprofits, government programs, and small tech consultancies) to understand potential project needs, expectations for collaboration, and views on connecting community needs to student learning. We analyzed these interviews to understand barriers and identified three themes around the central concept of misalignments: misalignments between the professional and non-profit world versus the educational system, misalignments between the goal of delivering project impact versus the goal of completing a course or developing a career, and misalignments between expectations of professionalism versus the reality of volunteers and learners. We conclude by reflecting on approaches to overcoming these misalignments and implications for designing computational ecosystems that support educational experiences more integrated with the community