While the European Union (EU) does not recognize any legal Israeli sovereignty over the territories occupied by Israel in 1967, it does not grant preferential access to the EU market for goods produced in the Israeli settlements in this area, contrary to the preferential treatment for goods produced in Israel. This situation is different, however, as regards the United States (U.S.) trade policy, which does not make any distinction between goods produced in Israel and in the Occupied Territories, since it grants the preferential access to both. Furthermore, the currently suspended negotiations of the super-regional trade agreement called the Transatlantic Trade and Investment Partnership (TTIP), spurred the enacting of a law that set the principal negotiating objectives of the U.S. regarding commercial partnerships, which included some provisions to discourage politically motivated economic actions against the State of Israel. As TTIP embraced the free trade agreement between the EU and the U.S., the EU differentiation policy could become problematic for the two partners, which despite the failure of the negotiations, revealed much about economic diplomacy. Consequently, this article attempts to show the different approaches adopted by the two trading powers, in order to deal with the dispute over the treatment of products exported to the EU from the Occupied Territories.