Trans-media is the new configuration of behavioral and cultural dynamics to transmit knowledge, tell stories, share ideas and experiences, promote diverse kinds of entertainment through more digital platforms. Hence, it is going to become a new form of social and cultural capital. The implications of this revolution are evident in many ambits: from the hyper-structured narration to the multiplication and accumulation of signification processes, from the cross-breeding of codex to the reciprocal contamination of expressive forms. Consequently, for some years now, "trans-media" has become an expression of symbolic value not only from the linguistic and semiotic point of view. Moreover, it is a "gate of culture and communication" for modern society, as well as a signal of crossing toward a new paradigm that completely changes the mechanisms of cultural industry and traditional communication models, such as the Dayan and Katz representation about big media ceremonies and Eco’s enunciation’s semiotic model. Some years ago, digital media (smartphones, social networks, chat-rooms and so on) were means of expression and amplifiers of ideas, media contents and broadcasting formats. Nowadays there is a turnabout: the digital and social devices impose a bottom-up system to the broadcasting industry with new cultural phenomena and formats, as well as self-promoted talents, new habits and trends, to which broadcasting systems are trying to adapt themselves. In the cross-media field, there is a rapid passage from cross-media level 1.0 (defined pushed) to cross-media level 4.0 (defined Experiences). In the first and second cases, the enunciation’s process and the amplifier effect of digital media is designed, checked and managed from the cultural industry. Whereas in the third and fourth cases, the user, through an active use of cross-media, is rendering a new form of cross-culture construction (through the collaborative construction of meaning). In cross-media Experiences, the origin of the cultural phenomenon derives from the digital user directly on the web (cultural self-production) and then spreads to other devices. The resonance of the bottom-up phenomenon and cultural label, which is attributed to multi-users generated contents, catapults in the media market, changing the broadcast dynamics. The culture, transmitted through cross-media systems, transforms the process of socialization and construction of people’s identity. Therefore, the cultural background is constructed peer to peer on line for emotional connections, thus “colonizing” the cultural network within the intergenerational relationships at home and at school. It creates new mechanisms of cultural mediation and changes the perceptive, cognitive and emotional orientation when compared with unpredictable situations as well as daily problems. The new communicative paradigm of transmedia changes also the educational context, that must to give adequate competences to be conscious citizens in the digital era. In this framework, also digital literacy and digital education have to update and innovate as digital knowledge and skills and didactic strategies. This chapter starts from the description the theoretical framework of transmedia paradigm and tries to translate it in the conceptual perspective of Digital Literacy and Digital Education, focusing on new kind of competences to develop.