The paper makes a critical analysis and a comparative review of key focal points in the policies of digitalization in education, reflected in the main national (Bulgarian) and European strategic documents. This critical review aims to answer two research aspects: 1) the possibility for a “comparative periodization” of policies in the area of digitalization in a national (Bulgarian) and European context and identifying the main priorities therein; 2) the systematization of unresolved strategic and operational challenges for the future in terms of integrating digital technologies in education in Bulgaria and Europe. The results from the conducted review provide grounds for identifying the following findings in the two research aspects. First, within the monitored period of policy formulation and presentation of digitalization of education in Bulgaria, similar to the processes of strategic planning and policy creation in the entire European Union, three key stages can be identified, conventionally called – 1) policies of “initial implementation” of digital technologies in social life, including in education; 2) policies related to the effective and enhanced use of digital technologies in education, and 3) policies of the digital transformation and development of an effective global ecosystem for digital education. Second, the unresolved challenges in the area of digitalization of education both on a national and pan-European level remain in terms of several key aspects – a lagging behind in providing modern digital infrastructure and open-access quality resources for educational purposes; deficiencies and lack of confidence in terms of teachers’ educational digital competences, “delayed” access provision to quality digital qualification for education experts; heterogeneity and lack of consensual paradigms in the area of “digital education”.