Through readings of Jacques Derrida's "Of Grammatology" and 'The Age of Hegel', attention is given to two of the problematic types of relationships that philosophy can have with education (exemplified through Derrida's readings of Jean-Jacques Rousseau and G.W.F. Hegel). These engagements, alongside a reading of 'The Antinomies of the Philosophical Discipline: Letter Preface', show how Derrida's thought can prescribe no educational programme and instead troubles educational proclamations and certainties. Throughout his life, Derrida negotiated his relationships to the educational systems and institutions to which he was responsible (notably in his own teaching and through GREPH), these negotiations, though, were not indicative of a belief in any ontologically grounded educational truth. Quite to the contrary, as I will claim, Derrida's thought is remarkable for its deflation of the myth, stretching at least as far back to Plato's "Republic," that philosophy can discover and prescribe the practical means for its own educational good. The argument presented in this article is that Derrida's thought is particularly fertile when it comes to educational reflection precisely because it does not close down, presuppose, or prescribe, and that these characteristics also allow for generative contradictions in Derrida's educational and philosophical thought and practice.