This chapter aims to explore the role that social work can play in and after political conflict. Rather than approaching this from a macro perspective, focusing on theory or national welfare approaches, we address it at a micro level, focusing on the roles that individual social workers can adopt in contexts of conflict. Specifically, this chapter draws on the experiences of two social workers in South Africa during and after the struggle against apartheid. One social worker, a woman identified as so-called ‘coloured’, quickly became disenchanted with social work’s complicity with apartheid and left the profession to work within the mass democratic movement as an activist, as this was the only way to contribute to radical, structural change. The other social worker, a white man, was conscripted into the defence force and had to grapple with how to give voice to social work values from within the apartheid machine. Through the reflections of these two individual social workers, who worked ‘across the fence’, this chapter aims to tease out the day-to-day role that social workers, in diverse contexts, can play to express core social work values, such as human rights and social justice.