The scope of economic sanctions and the aggressiveness of their enforcement have increased dramatically since the early 1990s. This is particularly true of sanctions imposed by the United States, and is most evident in the U.S. sanctions regimes that are extraterritorial. One might think of extraterritoriality in U.S. sanctions regimes as having two generations. The first generation was the era of the Iran-Libya Sanctions Act (“ILSA”), the Torricelli Act, and the Helms-Burton Act, of the early and mid-1990s; the second consists of the sanctions regimes of the last decade or so. The differences between the two generations indicate a marked shift, not only in the explicit scope of extraterritorial sanctions laws, but also in the degree and nature of their overbreadth. This article will examine these issues, looking specifically at the cases of Cuba and Iran.