Postphenomenology emerged as a new philosophical discipline within the contemporary studies in philosophy of technology by Don Ihde and was further upgraded by Verbeek in his philosophical theory of mediation. This paper 1) compares the Human–Technology mediation relation in Ihde’s Postphenomenology to the Human–Technology alienation relation in Heidegger’s classical Phenomenology, 2) explores the schematic diagrams of Human–Technology–-World relationships of Ihde and Verbeek, and 3) argues that Postphenomenological relationships can be upgraded to a new version if the UML models in Software Engineering are to be used in schematizing the Human–Technology–World Postphenomenological relationships. We show through modeling an Online examination system scenario how Use-Case diagrams can give a better representation of Human–Technology relationships schema, and a better understanding of Human– Human relationships among the use of technology.