The United States government has imposed economic sanctions programs on Iran since 1979, following the seizure of the U.S. Embassy in Tehran. Until recently, the Iran Sanctions Act of 1996 (ISA) and its amendments were the primary forces restricting business between the U.S. and Iran. The restrictive measures focused particularly on prohibiting the U.S. from investing in Iran’s petroleum industry, aiming to control Iranian nuclear behavior by targeting the nation’s massive energy resources. However, the strict sanctions regime effectively prohibited all U.S. investments in Iran, any Iranian access to the U.S. banking system, and any commercial transactions between the U.S. and Iran. The landscape of business activity between the U.S. and Iran promises to change in the coming years with the lifting of many economic sanctions under a recent multilateral agreement, the Joint Comprehensive Plan of Action (JCPOA).
On July 14, 2015, China, France, Germany, Russia, the United Kingdom, the United States, the European Union, and Iran reached an agreement to ensure that Iran’s nuclear program would become exclusively peaceful. This agreement, the JCPOA, provides for limitations on Iran’s nuclear program in exchange for the lifting of certain multilateral and bilateral economic sanctions on Iran related to its historical nuclear activity. On January 16, 2016, upon the International Atomic Energy Agency’s verification that Iran had implemented certain nuclear-related measures, the United States lifted select economic sanctions on Iran. Although this move eliminated some barriers to trade between the two nations, the post-sanctions trade environment presents many hurdles for commercial transactions between the United States and Iran.
On September 21, 2016, the U.S. Treasury Department approved the first major post-sanctions deal between the U.S. and Iran: the sale of 80 Boeing airplanes to Iran’s national carrier, Iran Air. On December 11, 2016, Boeing and Iran Air signed the deal for $16.6 billion. According to Iran, the actual price of the deal will be closer to $8 billion. The Boeing-Iran Air deal is important to Iran because its aviation sector was harshly impacted by decades-long U.S. sanctions, under which it was unable to purchase American-made aircraft. The nation operates an old, degrading, and outdated fleet; currently, only 162 of Iran’s 250 commercial passenger aircraft are suitable for air travel. Iran’s dwindling fleet of civilian and military aircraft is largely due to the nation’s historical dependence on American-made planes, so its inability to obtain new planes under the decades-long sanctions regime has had a tangible impact.
Arranging financing for the Boeing-Iran Air deal has proven to be a particular challenge, as U.S. banks are largely prohibited from conducting direct transactions with Iran. U.S. financial institutions may now transact through intermediaries that maintain banking relationships or otherwise transact with Iranian financial institutions that are not on the SDN List. Critics of the Boeing-Iran Air deal have pointed out that Iran Air was initially on the SDN list because of its connections to the Islamic Revolutionary Guard Corps (IRGC); however, Iran Air was recently delisted as an SDN. It remains prohibited for transactions involving Iran to be routed to or through the U.S. financial system unless the transactions are exempt from regulation or authorized by OFAC. It remains unclear exactly how Iran will finance the purchase.
U.S. political opposition, primarily from the Republican camp, further complicates financing matters. Legislation pending congressional review aims to make it more difficult for the U.S. to transact with Iran. One such proposed bill would “prohibit the secretary of the Treasury from authorizing certain transactions by a U.S. financial institution in connection with the export or re-export of a commercial passenger aircraft to the Islamic Republic of Iran.” If passed by Congress, this bill would prevent U.S. banks from financing the Boeing deal and would revoke any OFAC approval of the sale granted prior to the legislation’s approval. Another such proposed bill aims to raise the cost of transacting with Iran by doubling the taxes a company owes when it exports to a country designated by the U.S. as a state sponsor of terrorism. If passed, this legislation would undoubtedly increase the cost of Boeing’s deal with Iran Air. President Trump has also been vocal about the possibility of renegotiating the terms of the Iran nuclear deal, although it would likely be difficult for him to renege on the multilateral agreement.
If all goes according to plan, aircraft deliveries under the deal are expected to begin in 2018. 
 See U.S. Department of State, Iran Sanctions, http://www.state.gov/e/eb/tfs/spi/iran/index.htm. The U.S. has also worked multilaterally with the United Nations to sanction Iran’s oil industry in an effort to curb Iran’s nuclear program. See, e.g., U.S. Department of State, United Nations Security Council Resolutions, http://www.state.gov/e/eb/tfs/spi/iran/resolutions/index.htm. These resolutions include UNSCR 1929 (2010), UNSCR 1803 (2008), UNSCR 1747 (2007), UNSCR 1737 (2006).
 50 U.S.C. § 1701. Amendments include the Comprehensive Iran Sanctions, Accountability, and Divestment Act (CISADA), which added new sanctions and significantly expanded sanctionable energy-related activities. In the year leading up to the passage of the ISA, President Bill Clinton issued several executive orders in an effort to tighten the sanctions regime. See, e.g., Executive Order 12957 of March 15, 1995 (prohibiting U.S. investment in Iran’s energy sector); Executive Order 12959 of May 6, 1995 (prohibiting U.S. investment in and trade with Iran).
 The JCPOA specifies numerous guidelines that Iran has agreed to abide by in reducing its nuclear program. Iran will begin phasing out its IR-1 centrifuges and will not manufacture or assemble other centrifuges. Iran has committed to maintaining a specified cap on its uranium enrichment capacity and to conduct enrichment research and development in a manner that does not accumulate enriched uranium. It will also maintain a maximum uranium stockpile. Finally, Iran will convert its Fordow nuclear facility into a nuclear, physics, and technology center. See JCPOA, Nuclear: A. Enrichment, Enrichment R&D, Stockpiles (2015).
 OFAC simultaneously granted a license to Airbus for a $25 billion deal with Iran Air. Although Airbus is headquartered in France, the company required OFAC approval for the transaction because more than 10 percent of the manufacturer’s components are of American origin. See Jon Gambrell, US Grants Airbus, Boeing a Chance to Sell Airplanes to Iran, Bloomberg, Sep. 21, 2016, https://www.bloomberg.com/news/articles/2016-09-21/urgent-airbus-says-us-grants-license-for-planes-in-iran-deal. It is significant that Boeing and Airbus are the major players in the aviation industry and both require OFAC approval in order to transact with Iran. This is a point of vulnerability for Iran because the country is in dire need of new commercial and military aircraft. Crucially, this requirement encourages compliance with U.S. regulations, JCPOA measures, and contractual agreements that prohibit diverting aircraft toward terrorist activities, as Iran has few other choices in the aviation sector.
 See Thomas Erdbrink, Iran and Boeing Sign $16.6 Billion Deal on Sale of 80 Aircraft, The New York Times, Dec. 11, 2016, https://www.nytimes.com/2016/12/11/world/middleeast/iran-boeing-airplane-deal.html.
 Charles Riley, Iran says Boeing deal will cost just $8 billion, CNN Money, Dec. 26, 2016, http://money.cnn.com/2016/12/26/investing/boeing-iran-price-tag/.
 See Omar S. Bahir and Eric Lorber, Boeing’s Art of the Iran Deal: How to Use Civilian Aircraft to Pressure the Regime, Foreign Affairs, Aug. 28, 2016, https://www.foreignaffairs.com/articles/iran/2016-08-28/boeings-art-iran-deal.
 See JCPOA FAQs, supra note 6, at 18.
 See To prohibit the Secretary of the Treasury from authorizing certain transactions by a U.S. financial institution in connection with the export or re-export of a commercial passenger aircraft to the Islamic Republic of Iran, H.R. 5711, 114th Cong. (2016).
 See Bart Jansen, House to debate blocking loans for Boeing sale to Iran, USA TODAY, Nov. 10, 2016, http://www.usatoday.com/story/news/2016/11/10/house-debate-boeing-plane-sale-iran/93601314/.
 See Preventing Investment in Terrorist Regimes Act, H.R. 5545, 114th Cong. (2016).
 See Mahita Gajanan, Boeing Sells 80 Planes to Iran in $16.6 Billion Deal, Dec. 11, 2016. http://fortune.com/2016/12/11/boeing-iran-air-deal/.