Community health workers (CHWs) are central to the global health response to crises like the AIDS epidemic. Yet community health work remains undervalued and undercompensated worldwide owing in large part to the gendered and racialized contexts of care work. This paper investigates the possibility of occupational security for CHWs by comparing two cases from South Africa’s response to AIDS. The first draws on ethnographic research (2007–2009) in rural KwaZulu-Natal province and documents the fraught formation of a union representing CHWs. The second examines legal action in the Free State province for a group of CHWs known as the Bophelo House 94, who were arrested and criminally charged in June 2014 after protesting their sudden dismissal by the government. This case comparison finds that collective action has thus far had limited effects on CHWs’ position as a nascent occupation. The South African Ministry of Health has obstructed CHW professionalization, and non-state actors’ involvement has been a mixture of benefit and impediment: some social justice agencies have facilitated CHW advocacy, while many AIDS service organizations have cooperated with the state and exacerbated the precarity of CHWs’ working conditions. However, the consolidation of CHW work roles—owing to advances in AIDS prevention and treatment—holds promise for future CHW collective organization.