The tools for making the network smart are widely available and tested, although the learning process is always ongoing and is now geared towards the inclusion of new market players such as aggregators and energy service companies (ESCOs). The smartening process has determined an effort on infrastructures of the system, especially those related to information and communication technologies (ICT). In fact, one of the characteristics of the smart network compared to the traditional network is, in fact, the large amount of data exchanged, often in a bidirectional way, the efficient management of the system and the optimization of energy flows. In addition, the data make it possible to improve system maintenance, since the infrastructure can send signals to correct potential technical problems in advance. Investments in ICT are indeed at the heart of the Smart Grid concept and also central in the deployment of Energy Communities (EC): starting from general considerations about potential problems in data management and use in the Smart Grid, we can derive some key points to overcome barriers to achieving the goals of the energy transition. This chapter addresses the topic of digitalization focusing also on the information flow expected to be generated by the new entities envisaged by international regulators, and in particular aggregations of consumers in the form of EC. Widespread adoption of a typical Energy Community Scheme is far from being realized, and yet several implications arise, ranging from market design issues to financial and regulatory challenges, as well as negative externalities on the prosumer privacy side.