To what extent can Aquinas' philosophy of truth accommodate ambiguity? If an ambiguous object is that which exhibits multiple conflicting meanings, and truth, as ‘the conformity of thing and intellect', has its source and purpose in the divine, does the ambiguous lead us away from God? If so, how do we square this with the experience of the ambiguous, such as in art, that appears to draw us towards the divine? The paper explores this aporia by an analysis of the first two questions of De Veritate in conversation with Feser's Scholastic Metaphysics and Pickstock's Truth in Aquinas. Drawing on these three sources, truth is posited as a translation of being. However, it becomes clear that any translation is imperfect, given the difference between the medium of the existence of the thing and the medium of truth in the intellect. Hence, multiple, sometimes contradictory, propositions are needed in order to express the being of the thing. Moreover, it is shown how the ambiguous can prompt recursive returning to the singular, drawing us beyond merely identifying ‘what' a thing is, and beyond propositions, to share in the divine actualization of existence.