Throughout history, philosophers have reflected on educational questions. Some of their ideas emerged in defense of, or opposition to, skepticism about the possibility of formal teaching and learning. These philosophers include Plato, Augustine, St Thomas Aquinas, Søren Kierkegaard, Martin Heidegger, and Ludwig Wittgenstein. Together, they comprise a tradition that establishes the impossibility of instruction and the imperative to undertake it. The value of this tradition for contemporary education is that it redirects attention away from performance assessments and learning outcomes to (...) the ethical, aesthetic, and metaphysical dimensions of schooling. I argue that philosophers of education are uniquely responsible for teaching this tradition so that instruction might be undertaken in the right spirit. To this end, my essay is divided into three parts. In the first part, I explain why instructional skepticism has not been prominent in philosophy of education. I follow up, in the second part, by clarifying my choice of the term ‘instruction.’ In the third part, I sketch the instructional philosophies that ‘book-end’ this tradition: those of Plato and Wittgenstein. (shrink)