This paper examines the transmission of a segment of Avicenna’s De Anima (al-haywiyya) from Arabic, to Latin, to Middle English in order to demonstrate the impact of his theory of the imagination on late-medieval English culture. By demonstrating the evolution of Avicenna’s terminology as it was adapted to shifting intellectual contexts in late-medieval England, this argument offers a new methodology for the study of literary and intellectual history that does justice to the Arabic inheritance of Western thought. The critical term “New Aristotelianism” is symptomatic of a modern tendency to credit Arabic philosophers with having transmitted the works of Aristotle to the medieval Western world, but to oversimplify and diminish the impact of the Arabic sources themselves in the process. This oversimplification perpetuates the claims made by the earliest Latin translators of Avicenna’s The Healing (al-shifā’), who packaged the Arabic text as little more than a vehicle for Aristotle’s metaphysics. In fact, Avicenna’s revisions of Aristotle’s philosophy to accord with Islamic monotheism enabled it to permeate medieval Christian theology. Indeed, his theories were widely influential in their own right on later-medieval science, philosophy, and medicine. This study takes as its focus the trajectory of the concept of the ‘imagination’ (khyāl) as it moved from Arabic, to Latin, to Middle English. In the Middle Ages, imaginativa refers specifically to the cognitive process through which the mind transforms sensory experience of the physical world into units of memory and processes of reasoning. Avicenna placed uncommon weight on the importance of engaging with and evaluating the evidence available in the temporal world, a view that challenged the traditional Neoplatonic opposition between the physical senses and the intellect. As Avicenna’s closer alignment between sensory experience and the power of reasoning became more widely known, it complicated the established belief that the world was a site of temptations to be avoided. In the context of Latin scholasticism, this contentious idea led to intense theological and political backlash. In the context of Middle English poetry, it led to unprecedented creative freedom. By asserting that the physical world provided evidence that could be learned from, Avicenna’s theories enabled those without ‘authority’ in the traditional sense to validate themselves as interpreters of the world around them. By examining the various strategies through which translators adapted Avicenna’s theory to new contexts, this paper illuminates the nuances of cultural interactions between Arabic natural philosophy and medieval English culture.