The article presents the problem of a comprehensive analysis of the socio-cultural prerequisites that determine the successful or unsuccessful implementation of the program of digitalization of the regions of Russia. A detailed examination of the tools for assessing the level of digitalization on the example of the methods for calculating the Skolkovo “Digital Russia” index and the regional digitalization index by I. V. Groshev and A. A. Krasnoslobodtsev showed their low informative value for understanding the factors leading to the formation of digital inequality in regions. The actuality of the problem is due not only to the need for an adequate assessment of the tools offered as convenient for comparing regions, but also by the following facts. On the one hand, the tasks of digitalization of education are of paramount importance in the framework of the federal development program. On the other hand, their implementation depends both on the local state of educational institutions and on solving a wider range of issues: staff training, providing employment opportunities for graduates, forming the need for highly qualified personnel in the region, etc. The novelty of the work is that the author consider the problem of studying the digital inequality of the regions of Russia with an emphasis on the issue of digitalization of education in the context of the existing regional socio-cultural prerequisites that determine the successful implementation of programs or prevent it. The application of institutional and functional approaches is of particular research interest, these approaches allow us to study the existing socio-cultural prerequisites in the regions as factors of stratification of Russian society that strengthen or weaken social inequality in the context of the development of a digital society. The author concludes that the solution of the problem of a comprehensive assessment of the socio-cultural prerequisites of the regional level of digitalization requires a detailed multi-factor analysis on a specific problem and direction of digitalization. The comparison of such data requires separate consideration of the indicators of socio-economic, demographic, and institutional development of the regions.