Kant’s thoughts on language as a practical tool of what he would call “pragmatic formation” in his pedagogical writings are often overlooked. If anything, Kant is read from selected passages of his third Critique as being opposed to the arts of oratory and persuasion. This chapter will canvas Kant’s supposed animosity to the persuasive employment of language – rhetoric, in a term – and detail the complexity that lies behind Kant’s reaction to language as a tool of action among moral agents. Drawing upon his anthropological lectures and writings, as well as his religious and aesthetics work, I will argue that Kant leaves space in his system for a moralized, and moralizing, use of persuasive language in human community. Language use can draw upon inclinations and desires in an agent, and thereby compromise their autonomy. Yet there are ways that Kant speaks of or hints at that use language in ways that move us to be free. Kant’s aesthetics also allows room for vivid presentations as a way to make clear to one’s listener what one already knows in a nonmanipulative manner; these presentation styles are tied in with Kant’s religious thought, as well as with the western rhetorical tradition in general.