“Austrian” (or “Austro-German”) philosophy of language is characterized, among other things, by the following two features: (1) Problems of language are considered within the broader framework of an intentionality-based philosophy of mind—or, to put it more precisely, questions of meaning are considered as involving a quite articulated theory of intentions; (2) several aspects of such an account are explicitly presented as inspired by or somehow already at work in the Medieval Scholastic tradition. In this study we follow the track indicated by these two features and use some “Austrian” reflections on the articulation between meanings and intentions as a “heuristic filter”, as it were, to shed a new and different light on some Medieval debates in philosophy of language on the relationship between significare and intendere. It will be roughly divided into three parts. We begin by singling out some distinctive tenets of the “Austrian” strategy aimed at describing the relationship between meaning and intentions (section I), and then turn to various Medieval texts from the 13th and 14th century dealing with the two related notions of significatio and intentio (section II). The upshot of our investigation is to show how, for both “Austrian” and Medieval philosophers of language (and beyond their differences), a proper understanding of linguistic meaning—in the twofold sense of words or sentences having a lexical content and utterances having a determinate pragmatic function—presupposes an account of what one could call the “agentive intentionality”, i.e. the complex intentionality proper to practical goal-directed human behaviours. Some final remarks about outcomes, meaning, scope and perspectives opened by the method applied will conclude the study (section III).