In this paper, I defend the viability and relevance of Heidegger's philosophy of technology and consider its emancipatory potential in the field of education. First, I situate Heidegger's philosophy of technology within the broader emancipatory project of his early work--the fundamental ontology of Being and Time--and emphasise the role of language and (self-)appropriation in human subjectivity. Second, in light of the importance Heidegger placed on education for resisting the reifying and alienating effects of technology, I conclude with some critical reflections on recent attempts to develop a positive Heideggerian programme of education. In particular, I reveal some crucial limitations of the pragmatist or 'bodily coping' approach--defended by Hubert Dreyfus and Mark Wrathall and argue that an 'appropriative' alternative yields a more compelling philosophy of education, which emphasises the cultivation of moral articulacy.