The number of workers on the border between self-employment and employment strongly increased across Europe over the last decade. This paper investigates whether and in what respect these workers differ from employees and self-employed and analyses whether these work relationships are a stepping stone to more stable employment in the short-run using Italian data. Depending on the data source the “para-subordinates” represent between 1.8% and 5.3% of the Italian labour force. Since most of them work only for one company and are strongly integrated into the firm of the contract partner, we argue that labour and social security law discriminates against these workers who are in fact very close to employees. We find that they are not low qualified workers, but young, highly educated professionals. At the same time these contracts are not a port of entry into the labour market nor do we find that they are a vehicle to more stable jobs. However, they are a possibility for women to work part-time.