Nothing reveals the differences between an internal (i.e., inherently pedagogical) reflection on educational processes and an external (i.e., derived from a philosophical, sociological, psychological, theological or other perspective) more clearly than the differing attitudes towards alienation. Looked at from outside a pedagogical context, alienation appears only negative, deserving nothing but contempt and rejection; examined from inside a pedagogical framework, it proves to be a "conditio sine qua non," the process through which transformative education is possible. This article juxtaposes both perspectives in order to defend the conviction that within educational reflections, only an inherently pedagogical, i.e., positive, understanding of alienation is persuasive, whereas other approaches by definition either are outside of pedagogical reflections or belong to a kind of metaphysical thinking that nowadays seems rather outdated. This paper forms part of a Special Issue titled 'Beyond Virtue and Vice: Education for a Darker Age', in which the editors invited authors to engage in exercises of 'transvaluation'. Certain apparently settled educational concepts (from agency and fulfilment to alienation and ignorance) can be radically reinterpreted such that virtues can be seen as vices, and vices as virtues. The editors encouraged authors to employ polemics and some occasional exaggeration to revalue the educational values that are too readily accepted within contemporary educational discourses.