Iconoclastic and iconophilic impulses have long vied for pre-eminence in Christianity, coming to one particularly fraught crisis point in the Byzantine Iconomachy of the eighth and ninth centuries. Funding both impulses, this paper argues, is a profound Platonic ambivalence about the image. For Plato, the image not only deceives and enslaves; it also reveals and inspires. Plotinus, Gregory of Nyssa, Augustine, John of Damascus, and Theodore of Stoudios articulate their own iterations of Plato’s hopes and fears about the image as they attempt different strategies for resolving these dueling inclinations. This paper traces the evolution of image theory across these thinkers to illumine how Theodore of Stoudios’ approach magnifies Platonic image hopes and quells fears in a way that prepares for the ongoing resolution of image anxiety in the iconographic tradition. More than a purely historical interest, this arc of image thought have continuing relevance for image theory today.