The 9/11-inspired airport security screening system has been the center of controversy ever since it was created in 2001. Although the federalized system is held in high esteem by the traveling public, two tests of the system by the Department of Homeland Security (DHS) in 2003 and 2004 to 2005 found significant shortcomings, despite large changes made to the security screening process as a result of the first test. The article identifies other criticisms of the Transportation Security Administration (TSA) from both an operational and philosophical perspective, and from functions the TSA does do right. Finally, the article identifies why airport security privatization has not progressed and how potential changes to the TSA structure could make it a better functioning entity, including the author’s proposal to transfer TSA oversight responsibility to the U.S. Coast Guard.