This paper addresses an analysis of contemporary, structured, and connected pedagogical approaches to the teaching of digital proficiency/fluency in 21st-century digital literacy. We present a proof of concept and epistemological valorisation of digital literacy previously underestimated. This epistemological valorisation focuses on teaching digital literacy through understanding how teachers work - pedagogical planning, teacher training, syllabus design, practical work - enabling us to train technology producers instead of passive technology consumers, to enable agents instead of clients. The term “digital” will refer to 21st-century digital literacy. To “think digital” will refer to the mental process carried out by digital natives when conducting operations involving ICT - as their native language and framework. The pedagogical background is paramount to the structures underlying teaching of 21st-century digital literacy, characterised by its disruptive building process achieved through the acknowledgement of epistemological foundations. High school teaching of 21st century digital literacy is by no means at ground zero. The fundamental concepts to be conveyed remain the same: electric coding, input and output devices, memories, processors and transistors – the process/system is just faster and smaller. The development of a proof of concept was built according to a DSR framework, in an iterative way, giving evidence of architecture configuration, an asset of information, of tools, procedures, and attitudes.