A thorough understanding of the environmental and structural factors that precipitate unsafe sexual practices is necessary for HIV/AIDS-prevention research among high-risk population groups like commercial sex workers. I examined how poverty contextualizes sexual health behavior, including condom compliance among commercial female sex workers in a red light district in Calcutta, India. For my research I did an ethnographic study and conducted in-depth interviews of 37 commercial female sex workers. I found that poverty, instead of serving as a catalyst for poor health choices among sex workers, acted as an impetus for pursuing safe sex practices and remaining healthy. The results indicate that sex work, poverty, and health do not always have a paradoxical relationship.