One of the most challenging questions of education in late modern society concerns technology. Development and use of technology is altering our views of world and humanity. In this paper I explore philosophical background for a new kind of critical education that would be up to date with the changed world. This paper introduces case philosophy that German philosopher Gunther Anders demonstrates in his main works. The case philosophy is explored in relation to modern rationalism and phenomenology. For to show the intelligibility of case philosophy in the educational context, I first reject modern rationalism as an overly restricted approach to the world for it to be a feasible framework for case philosophy. Therefore, I examine phenomenology, as defined by Heidegger, as a reasonable background for case philosophy. Case philosophy requires the development and use of imagination, which entails exaggeration. In case philosophical thinking the contemporary phenomena are illuminated in their worldliness. Following the exploration of case philosophy, I discuss case philosophical understanding of education in the world of technology. (Contains 2 footnotes.)