The social transformation required in a democratic South Africa can only be achieved through the transformation of perceptions and attitudes. This article argues that community interaction can play an important role not only in raising the level of societal awareness of students, but also in the development of a symbiotic relationship between an academic institution and its surrounding society. Although this process has become a common feature in many universities, evidence suggests that engagement which leads to true social transformation, including a change in deep-seated attitudes, is rare. Consequently, community engagement risks remaining unprogressive, and has the potential to reinforce the very discriminatory attitudes and practices which it aims to overcome, while serving as a superficial response to institutional social responsibility imperatives. Through an analysis of a case study from the Visual Arts Department at Stellenbosch University, the article engages with the problems that emerge as barriers to social transformation in the relationship between the academic institution and the community, and argues that, in order that its emancipatory potential be realised, the politics surrounding community engagement, particularly its relation to social transformation, need to be identified and challenged.