The article presents the results of testing the concept of media generations, focusing on media users in pre-digital and digital information and communication spaces. To identify the characteristics of the media generation of the “digital frontier”, I rely on the concepts of the generations of C. Mannheim and M. McCrindle, the model of conjugation of technology and the human body by M. McLuhan, the ideas of the phenomenologist T. Fuchs about procedural memory, the explanatory model of the formation of generations by H. Becker. The application of qualitative research methods based on in-depth interviews (N = 30; Urals Federal District, Russian Federation) allows us to understand the essence of the media generation and identify its unique features: its transitional nature and role as a kind of frontier between “analogue” and “digital” audience media. The most significant markers of the “digital frontier” are ambivalent media patterns in the information technosphere, which are due to the sustained interest in the media of the analog period and the possession of digital skills that let one join the “digital lifestyle”.