One of the true revelations of treating diplomacy as a susceptible to nontraditional practitioners has been the reanimation of the matter of representation. It has sharpened focus, for example, on the distinction between status (who can claim to be a diplomat) and capacity (what it is that diplomats do). There is the seemingly interminable question of where the line must be drawn to signify the minimum qualifications to do the work and do it responsibly. Ultimately, however, the significance of the diplomatic actor lies within its powers. Examples abound in which the effective exercise of such powers, including negotiation, mediation of estrangement between parties, and especially representation defy the diplomatic actor archetype, which makes for a more complex system but, as this chapter will argue, one that is better matched with a complex world. As today’s nation-states struggle to carve out and maintain sovereignty in the face of so many challenges, so too do the systems they both support and need to survive. This chapter surveys recent elements of disruption in territorial and intellectual landscapes to assess our evolving understanding of diplomatic representation.