Introducing community engagement to my annual class of Visual Art honours students has become increasingly challenging. There is a healthy resistance to the perception of ‘cultural tourism’, and students are sensitive to the idea of entering a community as voyeurs with the perception of privileged “saviours”. I offer a particular example of an emerging annual exchange with the African Reclaimers Organisation (ARO), who have partnered with the University of Johannesburg (UJ) in a range of projects that can add value to upcycling of collected and sorted waste products. The pervasive news of corruption, violence, and rolling blackouts undermines well-being and increasingly perpetuates despair, apathy, or distraction. In this climate, a question of response in an educational environment is pertinent. How does one teach and learn about sustainable futures? How can educators foster empathy, agency, and activism among students? This article draws on ecology activist and scholar Dylan McGarry’s expanded concept of transgressive social learning using skills transfer through an apprenticeship, which is helpful in framing a model of teaching and learning based on social exchange. Including selected student reflections, the paper considers methods and practices that model ways to develop various forms of personal and social agency through exploring empathetic encounters.