This article introduces the special collection Teaching Late Latin: Past and Present, Challenges and Prospects and sets out a deliberately innovative, contrastive agenda for this issue of the Journal of Classics Teaching. While clearly programmatic in nature, this article advances a central claim: that examining the teaching of Latin in Late Antiquity and the early Middle Ages alongside the teaching of Late Latin today offers a productive lens through which to rethink Latin pedagogy across time. The special collection is structured around two dialoguing sections, Ars docendi antiqua and Ars docendi nova, which place medieval and contemporary classrooms side by side. In both contexts, teachers respond to shifting sociolinguistic landscapes with methodological creativity. By foregrounding these parallels, the volume challenges the widespread equation (still prevalent across much of the education system) of “Latin” with a narrowly defined Classical norm. At the same time, it calls for closer dialogue between philology and pedagogy, between historical transmission and present-day practice, and between scholars who research Late Antiquity and those who teach it. Our aim is not to offer definitive solutions, but to initiate a conversation. If this editorial has a programmatic edge, it is because we believe that reflecting on how Latin was (and is) taught is inseparable from reflecting on what kind of subject Classics wishes to be.