Remunerated sex work—sex for money or for non-monetary gifts and favors—is a controversial yet little studied topic in Tunisia--especially illegal sex work, which is widespread but difficult to investigate. The first part of the article discusses Tunisian civil law, which allows licensed FSWs (female sex workers) to work in brothels with medical inspection, regulated by the Ministry of Interior. The law prohibits unlicensed FSWs and all MSWs (male sex workers). Sex work was legal under the French Protectorate and after independence in 1956, Tunisia has kept this practice to the present. In 2011, after the the Tunisian Revolution, the Islamist party Ennahdha won control of the Tunisian parliament but made no effort to bring the law into accordance with Islam’s prohibition on sex outside marriage. However, during 2011 rioters attacked the legal brothels throughout Tunisia and caused almost all to close. Only Tunis and Sfax were left with legal brothels, and in those two cities the authorities have not been renewing the permits of FSWs. Thus FSWs have been pushed from legal to illegal sex work, which is widespread. The main body of this article is a series of case studies and interviews—a legal FSW, an illegal FSW, a former brothel keeper, a public health doctor who inspects FSWs, an STDs (sexually transmitted diseases) researcher, and an Islamist member of the Tunisian parliament. We summarize a 2015 Ministry of Health study on sex work and HIV/AIDS in Tunisia. The last part of the article discusses the normatively “grey zone” of sex that is remunerated in ways other than with money. We discuss the larger social context of changing sexual mores in contemporary Tunisia. Our conclusion is that the current practice of not renewing the sex work permits of FSWs contributes to the growth of illegal sex work and presents a public health danger because it undermines the control of HIV/AIDS and other STDs.