Within the framework of a transdisciplinary approach and based on years of empirical research, a socio-cognitive concept of digital socialization has been developed, reflecting the process of adaptation of a changing person to the opportunities and risks of a dynamic socio-technological environment. The key element of the concept of digital socialization is a hyperconnected, technologically upgraded digital personality as a part of a real personality; the concept reflects the current stage of the social and cognitive evolution of the human mind, when the developing consciousness actually merges with external tools (gadgets) and semiotic reality (the Internet). Digital technologies are being integrated into our cognitive and social system, determining the digital expansion (upgrade) of a person. Key dimensions of digital socialization are Internet hyperconnectivity, mixed reality, augmented personality, and digital sociality. Being hyperconnected to the Internet in mixed reality means not only the basic and defining characteristics of digital socialization for both adults and children, but also the main basis for the changes that are taking place with a person today. The extended self — a constantly developing cultural tool — is formed in its socio-technological embodiment, and it modifies the human ecosystem. The emerging and transforming personality expands and absorbs a technosystem as a significant element that promotes the implementation of psychological mechanisms of externalization and includes digital devices and computer programs along with methods of their application. A new anthropological type of digital man — Man Connected and Upgraded — lives in multiple realities and already interacts with inanimate systems (chat bots, household robots, etc.), so a paradigm change, an update of theoretical and methodological models is required. All this determines the cumulative nature of the theoretical and methodological approach, based mainly on the Lev Vygotsky’s (and his followers’) cultural psychology, which has absorbed classical and modern humanitarian and natural-scientific concepts. This approach is a promising basis for studying the specifics of digital reality, capable of withstanding the challenges of the “new normality”.