This chapter explores the topics and didactic strategies involved in teaching grammar through poetry in twelfth-century Byzantium by taking the prolific grammarian John Tzetzes and his Homerizing Carmina Iliaca as its case study. Tzetzes furnished his poem with numerous explanatory scholia, which give us a glimpse into Tzetzes’ teaching practice and illustrate how works of poetry served as model texts in the classroom of a grammarian. The chapter studies Tzetzes’ scholia against the background of the Art of Grammar by Dionysius Thrax, which was central to the Byzantine study of grammar and as such provides a relevant framework for analysing the grammatical material in Tzetzes’ scholia. By considering Tzetzes’ grammar lessons in the context of the various technical resources at his disposal and placing his scholia into dialogue with the scholarly and didactic works of his contemporaries Eustathios of Thessalonike and Gregory of Corinth, the chapter augments our understanding of Byzantine linguistic and literary thought.