After 1050 CE, medieval philosophers and grammarians used the traditional vocabulary and concepts of Latin grammatica as well as metalanguage and concepts derived from Aristotle and Augustine to describe and theorize language in structural and pragmatic ways. They never used the word pragmatikē or a Latin or vernacular cognate, but grammarians and philosophers reworked existing metalanguage, concepts, and theories to produce two new approaches to grammar and language. One theory, associated with the grammatica speculativa and related general philosophical grammar, adopted a framework based on Aristotle's causes to develop a theory of autonomous language according to the modi of being, understanding, and signifying. The modistae focused on the four orders of syntax: natural, grammatically obligatory, rhetorical, and logical (Kneepkens 1990). They sought to explain logical order, rather than word order, and congruitas with respect to semantic relations, much as modern generative and dependency grammars do. The other theoretical approach, which never really gained a name, combined Aristotle's account of language and mind with Augustine's theory of language and signs to confect a more functional perspective on communication and language in use. Aspects of medieval functional theories anticipate current pragmatic and functionalist theories of language and social interaction. In this chapter I discuss pragmatic thinking in mostly thirteenth-century philosophy of language with special attention to the work of Roger Bacon (OFM, 1214/1219-c. 1292) and Peter (of) John Olivi (OFM, 1248-1298). In Chapter 2 I zero in on a productive and provocative aspect of medieval grammatical and pragmatic theory, grammarians’ analyses of the interjection and ellipsis as meaningful language use outside explicitly logical order.