This exploratory paper identifies three challenges for community engagement in an Australian context. These are 1) institutional perceptions within the higher education sector when engaged approaches are not well understood or valued, 2) community perceptions based on distrust, and 3) a lack of support structures for sustaining engagement. I consider these challenges by reflecting on my own experiences of community engagement. I present a case study of a long-term community–university partnership with data comprising observations and field notes, individual interviews, group discussions, and participant reflections. This partnership aims to enhance educational opportunities for a Samoan-heritage community as it seeks to address significant resettlement issues in Australia. I respond to the three identified partnership challenges as follows. For the first challenge, I consider conditions inside universities that support mutual engagement and suggest how academics might develop as engaged scholars. For the second challenge, I explain the need for a methodology that builds relationships among community and university members, where mutuality and reciprocity, transparency, trust, and respect are valued. For the third challenge, I identify conditions on both sides of the partnership that sustain community engagement practices. The paper concludes with learnings that can usefully inform community–university partnerships and the planning of leadership teams within universities that seek an engaged approach for mutually productive linkages with community.