The purpose of the present article is to contribute to the postphenomenological theory of technological mediation by introducing a new type of ‘human-technology’ relation named ‘transcending mediation’. Previously postphenomenology didn’t pay much attention to the role technology plays in mediating human relation to Transcendence. This was because of empirical turn and pragmatism that are anti-metaphysical in their nature. In the present paper, however, I will show that the empirical element of technology can be balanced by some metaphysical findings. Keeping this (...) in mind, I will rely on Karl Jaspers’s metaphysics of ciphers in order to demonstrate how technology mediates not only our relation to the world but also shapes human’s relation to Transcendence. As I am going to show in the present paper, this sort of mediation becomes possible because technologies are actively participating in so-called self-transcending practices. The latter, according to Karl Jaspers, are practices through which humans can elucidate one’s true self (e.g., become an Existenz). In this article, I will take a case of Smart education as a particular type of self-transcending practice and will show how contemporary AI educational systems enable and disable particular forms of becoming true self (Existenz). (shrink)