This work aims to study the peculiarities of digital society development in Russia and Bulgaria in the context of the COVID-19 pandemic. In order to solve this task the authors used a variety of methods, namely comparative analysis, critical analysis, and case-stage method. The article analyzes the experience of the socio-political processes of digitalization in Russia and Bulgaria in the context of the self-isolation regime formation in both countries. The authors put forward a hypothesis that both countries have found themselves in recent months in the conditions of forced digitalization, which has left its mark on the processes of the natural evolution of digital society. The results of the study give ground to conclude that forced digitalization lies mainly in the intensification and randomization of digital communication flows, but not in the qualitative development of a digital society and the emergence of new technological solutions that could contribute to effective and meaningful socio-political development. The practical significance of the work lies in the comprehension of the current processes of the socio-political sphere’s digitalization and identifying key problems and challenges, without which it is impossible to successfully solve the problems of the transition of contemporary society to a new stage of its evolution in the digital environment.