Hippolytus’ fundamental mistake (hamartia) has been variously described as devotion to chastity (symbolized by his worship of Artemis), as life-denying puritanism or excessive arrogance (symbolized by his hostility to Aphrodite), and as a failure to progress to maturity via the normative rites of passage. This chapter explains Hippolytus’ failure in educational rather than initiatory terms. The play’s repeated references to Hippolytus’ youthfulness, its focus on the connotations of sōphrosunē (good sense, modesty), its depiction of Hippolytus’ failings, and its reliance on the vocabulary of teaching and learning all point in that direction. Comparison with Ion in his Euripidean name play further clarifies where Hippolytus’ education has fallen short. The empathy that Hippolytus manifests toward the end of the play for his stepmother, Phaedra, and his father, Theseus, is both tardy and partial; his suffering offers a salutary lesson for others, but not himself.