In this chapter, based on the authors’ sociocultural concept of media generations, which focuses on media users in the pre-digital and digital information and communication environment, we reveal the differentiating and identifying features of “analogue” and “digital” media generations and the intermediate media generation of the “digital borderline” in Russia, one of the post-Soviet countries. The result of the approbation is the development of an explanatory model of intergenerational communication in the digital media environment. The model includes interaction of three media generations as subjects of communication; three ways of transmitting experience combining post-figurative, co-figurative, and pre-figurative generational interaction; three levels of experience translation that contribute to bridging the digital divide generation cohorts: digital media technologies, everyday media practices, and sociocultural values. © 2023, The Author(s), under exclusive license to Springer Nature Switzerland AG.