This dissertation examines Plato's Protagoras and the parable of the cave in Republic VII within the context of the paradox of moral education. In light of the paradox, I show that Plato's critique of sophistic education in the Protagoras prefigures the positive account of education in the cave parable. In Chapter 1 Richard Peters' version of the paradox of moral education is presented as follows: if moral principles are imparted through non-rational means, then the educator will fail to develop the child's rational faculties; on the other hand, of the attempt is made to impart moral principles through rational means, then the educator will not engage the child's non-rational faculties and, thus, will fail to impart the principles. I re-formulate the paradox in terms of the tripartite soul and explain the conditions under which it applies to higher (as distinct from primary) education. The parable of the cave is then interpreted as Plato's attempt to resolve the paradox in these terms. In the parable, two models of education are contrasted, which I have labelled (1) the Conversion Model and (2) the Accretion Model. (1) is exemplified by the story of the escaped prisoner, and (2) is exemplified by the perpetual prisoners. Chapter 2 outlines the schematic structure of the Protagoras. I argue that the guiding issue of the dialogue is education, and that Plato conveys this concern dramatically by means of one of the dialogue's characters, Hippocrates. In Chapter 3 I argue that Hippocrates' remarks about his own education prefigure the Accretion Model of education in Republic VII and that Socrates' cautionary speech prefigures essential features of the Conversion Model. In Chapter 4 Protagoras' Great Speech is shown to assume the major features the Accretion Model. Chapters 5 to 7 analyze the remainder of the dialogue with an eye towards the two models of education. The dissertation concludes by returning to the paradox of moral education and Peters' response to it. I argue that his rule-based understanding of rationality and morality was, in fact, anticipated by Plato and shown to be inadequate. The Conversion Model is endorsed by Plato as an account of the transition from non-rational conventional education to a rationally oriented education; according to this model, education consists in a radical transformation of a person's valuational and epistemic orientation. The Accretion Model is attributed conjointly to conventional education and sophistic education; according to this model, education consists in an additive transformation of a person's stockpile of value-free knowledge. For the purpose of my argument, the crucial feature of the conversion experience is aporia (perplexity), which I examine in light of its epistemic status and psychological function.