This chapter explains why the school-to-work transition is so hard and long in Italy. The country represents a typical example of the South European school-to-work transition regime, where the educational system is typically rigid and sequential, the labour market has been recently made more flexible through two-tier reforms, and the family has an important role to absorb the cost of the passage to adulthood. The main thesis of this chapter is that the disorganization of the educational and training system rather than the supposedly low degree of labour market flexibility explains high (youth) unemployment. The chapter concludes by assessing the potentialities and shortcomings of the European Youth Guarantee as a tool to fight youth unemployment in the country.