This chapter discusses grammar and pragmatic thinking in the schools after 1050, focusing on internal history and semiotics. Roger Bacon and Peter (of) John Olivi proposed far-reaching theories of language and meaning with pragmatic perspectives. Bacon foregrounded pragmatic understanding in his semiotics of language and proposed context and communicative effectiveness rather than formal completion as the criteria for linguistic acceptability. Grammarians’ analysis of interjections, speech fragments, and emotional expressions opened new ways of understanding meaning-making, discursive interaction, and double articulation within a grammatical system and new pragmatic thinking about signification, reference, and affect. Olivi’s pragmatic approaches to some philosophical and theological accounts of language and expression focused on speakers’ and listeners’ responsibilities and how words’ meanings and contexts can change over time.