Health services, social welfare, housing and an adequate standard of living are all part of the economic, social and cultural rights which should be accessible to all. These rights are, however, not realised for all and societal resources are not accessible to all. In this respect, outreach work is a promising social work approach as it is often deployed to target, engage and bring individuals back into contact with services. Nevertheless, it is argued that outreach work leaves the mainstream unchallenged. We therefore examine the transformational potential of outreach work (Grymonprez and Roose, 2019). Theoretically, we draw on the concept of symbolic boundaries, which are conceptual distinctions drawn between people and groups. This article contains an in-depth analysis of outreach work practice with marginalised homeless individuals in the Belgian city of Antwerp. We identified three conceptual distinctions important for the construction of symbolic boundaries: predictability, complexity and housing readiness. Our analysis identifies a range of tactics used by outreach workers to transform these boundaries. Such tactics may be helpful for social workers interested in transformational practice in contexts where challenging the mainstream is not seen as a mandate for outreach workers.