In the decades immediately following the Vietnam War, there were no significant conflicts with free speech resulting from major policy or military action. In contrast, the global war on terror following the events of September 11, 2001, mirror in many ways where prior conflicts and government action clashed with Free Speech. Forty-five days after the worst attack on American soil since Pearl Harbor, Congress enacted the USA PATRIOT Act. In the months and years that followed, American forces fought abroad and opponents of and advocates for the Act fought at home. This article will review the implementation of the Patriot Act and two provisions, section 215 and 805, to follow the actions of the executive, legislative, and judicial branches of the federal government and those of civil liberties advocacy groups to review America’s efforts to meet the challenges of providing security for the homeland and protecting Free Speech.