Teaching ancient literature in translation is increasingly common across schools and universities; however, there has been limited discussion of pedagogical approaches towards, specifically, translated literature. I discuss the findings of a study conducted on first-year undergraduates at Oxford University, who analysed translations of the Iliad as part of a taught course. The publication of Wilson (2023) offers an opportunity to see how students respond to very recent translations. I explore the pitfalls students encounter when analysing poetry in translation and the ways educators, whether in high schools or universities, can help students negotiate these pitfalls and develop a more sophisticated understanding of literary translation. In particular, I discuss how a student’s level of familiarity with the Greek language affects the ways they analyse translations, and how educators can encourage students with little or no Greek to engage with translations successfully.