For many years, electronic communications has been one of the most important areas of policy intervention or the European Union. Liberalisation and privatisation of the telecommunications industry were very important topics of the policy debate in the two decades from 1990 to 2010. In these years, the EU developed a sophisticated regulatory framework aspiring to the principle of favouring the entrance of new players in the sector and characterised by a strong pro-competition flavour. More recently, however, the necessity of mobilising important investments for the creation of new Next Generation Networks, capable of delivering all the benefits of the digital revolution to European citizens, has cast doubts on the validity of the established framework. This paper discusses the solutions adopted during the liberalisation process and summarizes some of the key future challenges to the existing regulatory framework.