Transnational law both shapes and is shaped by policy decisions of public officials addressing global terrorist threats. These and other interrelated security and human rights concerns challenge executive officials in national governments and international organizations to simultaneously advance the rule of law and pursue other important welfare interests. This Article explores opportunities for transnational executives to improve their work and transnational legal frameworks. It proposes that behavioral insights into decision making and public policy making provide essential lessons for those efforts. The U.S. experience developing new policies to interrogate suspected terrorists following the Al Qaeda attacks of September 2001 provides a historical reference point to consider specific opportunities to improve transnational security decision making and transnational law.