From the Thesis Abstract: "The United States' investment in southern border security has consistently been a topic of discussion regarding technological improvements and measurements of effectiveness. There have been multiple failed programs designed to combine infrastructure, personnel, and technology, ranging from the America's Shield Initiative (ASI) to the Secure Borders Initiative Network (SBInet). These efforts have resulted in billions of dollars of wasted funding. The latest initiative, named the Southwest Border Technology Plan, claims to use lessons learned from previous failures and focuses on integrating systems tailored to individual sectors of the border. A related issue is the use of apprehension rates and other passive metrics as the measures of effectiveness for the security of the southern border, continuing the historical inconsistency of inaccurate reporting methods. The Department of Homeland Security (DHS) has recognized the problem of inadequate measurement and is developing new methods with the assistance of improved data captured with biometric systems; however, the issue of inaccurate reporting remains. An alternate and more active option to consider for measuring security effectiveness is red teaming. This thesis explores the following questions: what technologies are currently utilized for border security and how can their effectiveness be measured? And, can red teaming be used to improve on existing measures of effectiveness?"