The article focuses on Mazara del Vallo, Sicily. It aims to show how a group of Roma from Kosovo, living in the area since the 1970s, has gained a livelihood through such enterprizing methods as music, improvized handicrafts and small-scale drug dealing. Their precarious situation is conditioned in large measure by the complex interplay of state regulations and the practice of local authorities. Nevertheless, these individuals have been able to exploit the ambivalence of the authorities as well as opportunities presented by the thoroughgoing informality of this south-western Sicilian city. Although a culture of poverty perspective would suggest that they are merely reproducing poverty from generation to generation, in-depth observation shows that the informal economy represents a paradoxical means for social advancement.