This article discusses communication concepts associated with the practice of public diplomacy 2.0, applying those concepts to analysis of American implementation of PD 2.0 directed toward Iran, a country with which the United States has lacked formal diplomatic relations for more than 30 years. Although interaction between the United States and the Iranian people may be limited, may not always take place in real time, and certainly cannot serve as a substitute for the interactions facilitated by a bricks-and-mortar embassy on the ground, the Virtual Embassy Tehran and its social media accouterments represent an interesting application of American public diplomacy priorities. The effort is consistent not only with the goals of 21st Century Statecraft, but also with the Administration’s stated preference for engagement while still pursuing vigorous economic sanctions toward the Iranian regime. The effort also has potent symbolic value given the United States’ promotion of global internet freedom as a foreign policy goal. The case of American engagement with the Iranian people as examined here is a unique study in the practice of public diplomacy 2.0 and it offers an opportunity to test some of the more idealistic arguments associated with application of social media to diplomatic efforts.