Ruban L.S., Zybulevsky V.F. Paradoxes of the Digitalization and «Black Swan» of the Russian Reality. Drilling and Oil, 2020, No. 6, pp. 14-23. Ruban L.S., Zybulevsky V.F. Paradoxes of the Digitalization and «Black Swan» of the Russian Reality. Drilling and Oil, 2020, No. 6, pp. 14-23. ISSN 2072-4799DOI íåòÐÈÍÖ: https://www.elibrary.ru/item.asp?id=42999239Posted on site: 10.12.20 AbstractThe authors analyze the process of digitalization of production, management and social sphere in Russia, pointing out that digitalization involves the computerization of data, increasing their availability, transparency and openness of information and making it possible to counter corruption and copyright infringement. The article analyzes in detail the implementation of digitalization in the energy sector of the Russian economy with the identification of technical and social risks associated with this process. The article compares the Russian and Singaporean experience of digitalization development and provides a reference to the «black Swan» theory in relation to the Russian reality in the conditions of turbulence inherent in social changes.