The period between mid- nineteenth to early twentieth century was the time of increasing concern about sexually transmitted diseases and their society-wide flow as epidemics. Syphilis, which is quite often regarded as an “illness of the modern era”, perceived as an evil infirmity that could deteriorate future generations, obliterate fetuses and doom stricken families of different classes to unhealthy, jeopardized and tainted progeny. In addition to these, it was also an immoral malady which could destroy the fighting ability of men in arms and impair the honor of societies in which it broke out. In relation to rapid flow of syphilis among masses, different sets of reflexes and precautions emerged; such as growing concern towards the well-being and purity of families, systematic medical examination of prostitutes and control over prostitution, hospitals designed and built for locking and treating syphilitics in a compulsory way, and a whole set of strictly moral claims about the infected. Ottoman Empire was not an exception. Between 1850s and 1900s, syphilis became a multi-dimensional health disorder for Ottoman administration. Due to its quantitative and qualitative impacts over population, it was perceived as a serious encumbrance for the outfit and might of Ottoman society and state. In the medium of syphilis, repressive means were utilized to discipline different social groups in the empire; such as prostitutes, army conscripts and bachelors by compulsory medical controls and through long-term hospital confinements were among the repressive and disciplinary measures of the Ottoman anti-syphilis regulation. Medical professionals, magistrates of municipal and police administration, and community leaders were also held responsible to detect, record and report the ill. Ottoman advice genre on syphilis also elaborated certain points which were either visited passingly or non present in the scope of anti-syphilis regulations put in force. These works aimed to sustain regulations by providing practical instructions to the target population and agents, who were liable to enforce the preventive measures. They also provided information on the informal dimension of syphilis epidemics since they were written by literary figures who had a critical outlook, and area specialists who reported the reactions to, and the impact of the regulations in force. This paper will try to critically analyze these dimensions of anti-syphilis regulation in the late Ottoman Empire in order to portray the representations of the syphilitic and the syphilis as an illness as well as arguing the gendered nature of medical discourses over venereal disease.