The presented research aims to understand the educational value and further educational trajectories of digital platforms in the framework of mediated learning through an overlook on a digital online platform called “Education on Screen”. The approach of the platform supposes the representation of the mediator in learning through various multimedia texts including pictures, videos or pieces of music. The author is reviewing the trajectories of using online educational platforms as a learning environment in the framework of semiotics and Lev Vygotsky’s theory. Digital technologies are becoming a widespread solution in many spheres of human life, including the educational one. Digitalization is proving itself useful in various educational demands, such as language learning. Thus, educational materials are undergoing digitalization: printed handbooks are being replaced with online multimedia tools, whiteboards are being replaced with digital screens and students are enabled to use personal digital devices. At the same time online platforms appear as a digital way of classroom environment. As a means towards its goal, the paper analyses how the way of reading artistic texts, which is mediated with the online platform, shapes the way of learning and teaching. The learner’s perception in terms of digitized classroom is undergoing a series of changes consequently shaping the process of learning and presupposing the change in the approach to teaching. But it also opens a question on how meaning-making happens in the digital learning environment. As a result, it proves itself important to research the trajectories of the development of creativity and imagination in the context of digital platforms, that have to be considered in order to let them be important tools and parts of the learning process. The platform “Education on Screen” offers online solutions for digital learning in culture, history and literature, where a learner is offered to read artistic texts with the help of different online activities that offer various multimedia exercises based on the texts that belong to the transmedia reality of the studied text. The way in which digital technologies are used in the classroom shapes teaching and learning. Digital technologies can be used (1) in the form of the classroom design itself, where instruction and classwork are organized in digital space, (2) in the framework of digital activities or (3) as online educational resources such as educational platforms or websites. The author discusses the key features of the digitized learning and understanding cultural texts through reading artistic texts on the online platform “Education on Screen”. Some of the main challenges of a contemporary classroom are contrasted with the approach of the platform “Education on Screen” in the framework of digital education, Lev Vygotsky’s theory of psychological development and the principle of mediated memorizing and learning (Vygotsky 1979).