Cigarette smuggling in all its forms prevents the Greek state from collecting large amounts of taxes. The phenomenon has been largely neglected by the academic community and this is even more the case when it comes to bootlegging. This article is a presentation of the available evidence on two schemes of bootlegging cigarettes out of Greece. It explores the different entrepreneurial inputs of cigarette bootleggers, and the practices that resemble “normal” entrepreneurial activities, through two case studies. These inputs and practices shed some light on the environment in which unproductive economic activity takes place, offering researchers and policy makers insights into their manifestation.