This paper seeks to offer a new approach to the problem of meaning in Hans Holbein's Ambassadors. Widely recognized as one of the more enigmatic portraits of the Renaissance, interpretations of this painting typically issue from the contrast between literal and figurative meaning. What distinguishes my treatment of the painting is, first of all, the methodology I adopt in interpreting it, and, second, the surprising results that issue from this methodology.Instead of attempting to decipher the painting's symbolic scheme, I propose a philosophical account of the painting as a visual enigma, i.e., as an enigma that intrinsically belongs to the visual domain. I argue that the enigmatic character of the painting is tied to its unusual form of appearance, and I focus on the ways in which the painting's visuality is indeed exceptional, both within the framework of Holbein's work and within the larger context of Renaissance portraiture.The analysis of two unusual visual features (within their historical and pictorial context) leads me to claim that the Ambassadors is a painting concerned with a secret, a specific secret underlying the relationship between the two men it portrays, Jean de Dinteville and Georges de Selves. I argue that the intimate relationship between the two Frenchmen is of a kind that could not be openly expressed, and that the painting's peculiarity stems from the indirect manner in which it chooses to express its concern with this secret.