This book provides a snapshot of state-of-the-art interdisciplinary discussions in Russia about technology in the information society. New technologies are subject to original theoretical analysis, but there are also reflections on the practical experience of their application. The book covers a range of topics which includes human–technology interaction, education in digital reality, distance education due to COVID-19 quarantine measures, cognitive technologies, system analytics of information and communication technologies. The book collects contributions from philosophy, didactics, computer sciences, sociology, psychology, media studies, and law. It contains a selection of papers accepted for presentation at the XX International Conference «Professional Culture of the Specialist of the Future» (26–27 November 2020, St. Petersburg) and the XII International Conference «CommunicativeStrategies of the Information Society» (23–24 October 2020, St. Petersburg).