This article considers the complex ways volunteer outreach workers can frame their engagement with a community-based HIV prevention programme for South African township MSM. Drawing on research conducted during the Ukwazana programme in Cape Town it begins by exploring limitations towards MSM participation with programme facilitators (namely previous feelings of mistrust and community homophobia) and strategies developed to offset these concerns. It then considers how great care must also be taken to appreciate how volunteers from marginalised groups can frame training as a key condition for participation. To understand this it is therefore necessary for facilitators to acknowledge a number of additional concerns. These include community status, a lack of bonding social capital between volunteers and a highly developed from of critical consciousness by volunteers regarding HIV prevention possibilities. This article therefore suggests that effort to initially engage marginalised communities must also be met with effort to understand the complex ways volunteers relate to other MSM and to each other.