Self-employment represents a larger share of total employment in Italy than the European average, and in addition Italy has the larger number of self-employed with no employees. This article focuses on the link between companies' flexibility strategy and new employment positions and non-standard labour contracts creation. The analysis of restruction process (technological and organisational evolution) in a specific economic sector (publishing industry) shows an increasing use of sub-contractors and temporary self-employment home based workers, and un-conventional behaviour models from the labour supply side. The diffusion of such a new and mixed contractual forms of employment, shows the difficulty of drawing a clear dividing line between independent and dependent employment. A growing number of people with a vulnerable position in the juridical, economical and social domain represents a serious challenge to the national reforms in recent years. The public debate is actually relates to the need for some regulation of working conditions for these heterogeneous independent workers and to revise the social security system in order to reduce inequalities within this category and between it and dependent employment.