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The European Digital Agenda represented a priority of the Europe 2020 strategy for smart growth of the European Union, towards the objectives of Europe 2030. The article outlines the regulatory framework on the digital strategy in Europe and Italy, proposing a theoretical-methodological discussion on the evaluation of policies on digitalization. The national results are presented in relation to the DESI INDEX, the main European tool for the observation of socio-cultural changes resulting from investments in digitalization, in the pre and post COVID period, discussing on the current state of evaluation practice in the implementation of Digital Agenda in Italy. The policy cycle outlined by the EU 2021-2027 programming and by the Recovery Plan on the topic of digital transition leads to a discussion of the main challenges of the evaluation practice, evidence of the structural complexity of the policies on digitization, stressing the need for multifocal and pluralistic evaluative perspectives of programs. [ABSTRACT FROM AUTHOR]