Portraits of rulers, medals, and other images of politicians were widely used within early modern diplomatic practice. Historians have long appreciated the role of portrait exchange in early modern royal marriage negotiations. Far less appreciated are the prevalence of portrait exchanges between European monarchs outside of marriage negotiations and the diplomatic uses made of these, and other, royal portraits. Diplomatic art operated within a ceremonial and symbolic system where even small distinctions were imbued with considerable significance and where reciprocity, honour, prestige, magnificence, friendship, and concepts of gift-giving were crucial components in constructing its diplomatic meaning. Rulers' images played an important role in diplomatic strategy; their display advertised current and past political alliances and suggested the direction of future policy, while portrait gifts and personal interactions with portraits during diplomatic audiences created political intimacies, established confidences, and helped to maintain relations in strained circumstances. © 2014 Oxford University Press.