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The tortuous history of U.S. and international efforts seeking to address proliferation concerns raised by Iran’s nuclear ambitions reveals diplomatic failures as well as threads of diplomatic progress. Despite its uncertain future, the 2015 Joint Comprehensive Plan of Action (JCPOA), negotiated over roughly two years of intense diplomatic engagement among the P5+1, EU, and Iran, nevertheless remains by far the most significant achievement within this complex diplomatic history, having rolled back, halted, and opened up Iran’s nuclear program to what the IAEA termed “the world’s most robust nuclear verification regime.” Yet just over one decade ago, in October 2009, after years of stalemate following the first major public exposure of Iran’s illicit nuclear activities in 2002, and well before the JCPOA would come together, Iran tentatively agreed, in principle, to a significant confidence-building measure with the P5+1 regarding its nuclear program, often referred to as the “TRR fuel swap proposal.” While the deal ultimately collapsed and was overshadowed by subsequent events, the TRR negotiations were an important precursor that in many ways set the stage for events that led to the subsequent successful negotiation of the JCPOA. How did that initiative come to pass, how was it lost, and what can we learn from the experience as it relates to negotiating with Iran regarding its nuclear program?