Studying Virgil at school in Late Antiquity was challenging for students. Epic verse is both highly stylised and frequently archaic, set in a far distant mythological world that often required considerable explanation. In addition to teaching Virgil’s poetry, Donatus also taught his students the comedies of Terence, which present slightly different, but no less significant, challenges. Terence’s vocabulary and syntax were significantly archaic for late antique readers. Comedy is written in a far less formal register of language than epic verse. The natural idiom of late antique students would have differed significantly from that of Terence. Terence’s plays contain considerable humour, and this is particularly difficult to teach, since explaining jokes frequently ruins their humour. In this paper, I examine how Donatus addresses these various difficulties. I show how he dealt with linguistic challenges, such as archaic language and early conversational idiom. I explore the ways in which he tries to ensure that students understood the plot and action of the play. And finally, I evaluate how Donatus addressed humour. How did he ensure that his students understood the jokes without ruining their humour? I ground this analysis in what we know about the activities and interactions that took place in the late antique classroom. In doing so, I place Donatus into his educational context alongside Servius.