This thesis project is divided in two main parts. The goal of the first part was to develop a software tool which could help users identify illegal data transfers directed to non-EEA domains while navigating the web and generating reports which could be submitted to the Italian supervisory authority (namely Garante per la Protezione dei Dati Personali). The goal of the second part was to extend the work by creating a set of automatic scripts which could automatically navigate through websites and identify illegal request directed to non-EEA domains, and then run an analysis on the Italian public administration websites by using those scripts, possibly building visual representations of the obtained results.