Syphilis is an infectious disease. It is unique and interesting, and even to this day it continues to be a major challenge to the medical community in the prevention of the spread, the diagnosis and treatment of the disease. In recent years in Israel, 200 new cases have been revealed annually. During this period, several reports were published on the outbreaks of the disease. We believe that due to the increase in the rate of patients with the disease there is a strong need to educate the medical staff about the disease and to raise awareness regarding the symptoms of the disease, methods of diagnosis, increased risk populations, and methods of treatment. In this article we present four cases of syphilis that we encountered in our institution, which presented relatively in different ways. Furthermore, in these cases the diagnosis was not simple. So it is important to be aware that this disease still exists and must be recognized in order to know how to diagnose it.