Medieval Arabic literary theory (poetics and rhetoric) is often predicated on the ‘philological’ approach of its writers, in contrast to the ‘philosophical’ approach championed by classical Greek and Hellenistic scholars. One would thus expect to find a clear influence of the Arabic grammatical tradition, starting from Sibawayh, on the subsequent writings of literary theory. As of yet, however, such an influence has not been clearly identified (cf. Baalbaki 1983). One possible exception is the convergence of the notion of figurative language (majaz) with the term ittisa' ‘latitude’, first appearing in Sibawayh’s Kitab and referring to specific syntactic phenomena (Versteegh 1990, Levin 1997, Carter 2004, Dayyeh 2015). In the works of subsequent grammarians, ittisa' came to be used interchangeably with majaz, a term extrinsic to grammatical thinking. In this paper I explore to what extent the uses of ittisa' among the grammarians conformed to the way majaz would later be used in non-grammatical writings, primarily literary theory (naqd, balagha). I argue that while the grammarians had no direct interest in tackling metaphorical language, they nevertheless posited a competing approach to the one that would emerge in the field of poetics and rhetoric. This is especially borne out by comparing how the same poetic shawahid (illustrative examples) were treated by the grammarians vis-à-vis the critics. Even within the grammatical tradition tensions emerge between a ‘cognitive’ approach to metaphorical extension and a more syntactic one. Unraveling these differences in approach will prove instrumental to our understanding of the theory of majaz laid out by 'Abd al-Qahir al-Jurjani (d. 1078 or 1081), a scholar we identify today as a literary theorist but who, in his own lifetime, was a grammarian first and foremost. Early theories of figurative language have received much attention in the works of Wolfhart Heinrichs and others. However, its grammatical dimension has yet to be explored.