As of March 4, 2011, 33 vessels and 711 crew members were being held hostage by pirates. The international community has engaged in various efforts to address the continuing problem of pirate hijackings with seemingly little success. The United States has also taken its own swipe at piracy through Executive Order 13,536, entitled “Blocking Property of Certain Persons Contributing to the Conflict in Somalia” (Order), that was issued by President Barack Obama on April 12, 2010. Upon its issuance, the Order created a great deal of confusion and consternation with respect to whether it prohibited the payment of ransom to pirates. The answer as it emerged has proved to be “yes,” “no,” and “maybe” and has resulted in a process whereby applications for guidance with respect to the payment of certain ransoms (and related insurance payments) are made to the Office of Foreign Assets Control of the U.S. Treasury Department (OFAC). The authors of this Article have both been actively involved in the development of the application process and have represented numerous clients seeking guidance with respect to ransom-related payments. This Article explains the Order and its import for piracy situations, and details the authors’ experience with both the OFAC guidance process and related procedural and substantive issues that have arisen.