The development of information and computer technologies in modern conditions is influenced by a large number of factors that determine the success or failure of the digital transformation projects implementation. The purpose of this article is to study the determinants of digitalization in the regions of Russia on the basis of their classification and determination of their maturity level in terms of new technologies. The research methodology is based on exploratory cluster hierarchical analysis and cluster formation by the K-means method. The level of broadband Internet implementation, the use of cloud technologies, RFID and ERP systems, as well as the availability of electronic sales of goods and services in 2019 were identified as the studied determinants of digitalization. In contrast to previous studies, as a result of the classification, three stable clusters of regions are identified according to the level of digital maturity: advanced regions, regions with inertial development, and regions of the catching-up type of development. The factors influencing the digitalization index are determined. The level of digitalization of three clusters is compared with the indicators of digitalization in developed European countries. It is noted that the breadth of technology diffusion statistically significantly correlates with the financial and technological well-being of the regions, as well as the level of their innovative activity. The results can be used to develop a differentiated policy for the digitalization of regions, which is based on an individualized approach to determining key performance indicators for local transformation projects.