Task shifting from trained clinicians to community health workers (CHWs) is a central, primary health care strategy advocated by global health policy planners in resource-poor settings where trained health professionals are scarce. The evidence base for the efficacy of these programs, however, is limited—in particular, research that identifies their potential unintended consequences. Based on sustained ethnographic study of CHWs working for AIDS projects in South Africa at the height of the country’s AIDS epidemic, this article identifies how structural and local factors produced unintended consequences for CHW programs. These consequences were (a) CHWs moonlighting for multiple organizations, (b) CHWs freelancing in communities without regulation, and (c) adverse patient outcomes resulting from uncoordinated care. These consequences stemmed from structural elements of a bureaucratically weak health system and from local grassroots dynamics that jeopardized long-term CHW program sustainability and eroded national health goals.