Based on 14 months of ethnographic research in Grahamstown, South Africa, I argue that economic inequalities and structural barriers have created dire situations in which people living with HIV/AIDS (PLWHA) often are forced to choose between economic security and health security. While the rollout of antiretroviral treatment (ART) has been initiated in various stages throughout the country, the availability of treatment has created unanticipated and adverse responses. Many PLWHA who are too sick to work rely solely on social assistance grants as their only form of income. To qualify for what are locally known as “disability grants,” patients must demonstrate and maintain a CD4 count of 200 or below, which ironically, also is the marker to begin ART. This has created a complex dilemma as patients have begun to modify their adherence to and/or refuse ART to maintain low CD4 counts, in an effort to continue to receive their “disability grant,” thereby sustaining their economic and food security. Future HIV/AIDS programs must develop initiatives that do not conflict with patient treatment and prevention strategies but, rather, provide a holistic approach to economic and health security, particularly in resource-poor communities.