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Historical experiences show that the education systems have always responded to technological develop ments, although such changes are either confined to the optimization of the existing processes, or change the overall structure. To carefully analyze this schism, this paper uses a Comparative Historical Analysis (CHA) of four of the most important educational technologies: the ballpoint pen, personal computer, internet and artificial intelligence. Under the new six-dimensional analytical framework (measuring the Access Equity, Pedagogical Transformation, Epistemological Foundations, Student Agency, Teacher Role, and Institutional Effects), our analysis shows that a long-standing historical trend of optimization gravity is evident in which the transformative possibilities of the pen, PC and the internet itself was mostly appropriated to scale the industrialized model of education. To the point, artificial intelligence as a disruptive force is present in all six dimensions. It leads to an epistemological discontinuity through eliminating traditional authorship, challenging the knowledge authority, and making standardized assessment irrelevant. The results imply, it is necessary to carefully challenge their historical trajectory of optimizing for success in the age of AI. This requires dramatic policy and pedagogical changes, which require new assessment paradigms oriented at human skills with the adoption of strong ethical AI governance frameworks and teacher’s remaking in relation to the role of ethical mentor and learning aide. The future of education relies on steering this restructuring, which is inevitable, with a commitment to equity and human-centric values.