This chapter discusses ideas and the contribution of innovative philosophical concepts and educational values defended by the Brazilian didactic epistemologist Hugo Assmann and world-renowned philosopher of education Paulo Freire, who later applied them to the emergent context of implementing artificial intelligence tools in Brazilian public schools. Although they have worked together at the beginning of Paulo Freire’s dissemination of educational ideas and approaches, after Paulo Freire’s death (1997), Assmann continued to take Freire’s ideas to philosophical and epistemological depths in line with the sequence of digital technology improvements that occurred from the mid-1990s and during the early 2000s. However, the ideas, values, and educational concepts reflected by both remain valuable questions to provide us with enriching interpretative references.