The United States’ ability to conduct an effective irregular warfare campaign is hampered by political realities and Department of Defense cultural norms. While there are many overlapping deficiencies, this inaugural IWC Insights paper discusses three prominent barriers to success: 1) a quick-win culture that incentivizes short-term fixes; 2) the lack of adequate irregular warfare education throughout the interagency community; and 3) promotion and leadership selection processes that undervalue the development of necessary language, cultural, and regional expertise for irregular warfare application. Each of these problems often reinforces the others. The Irregular Warfare Center aims to empower and promote research, education, and engagement with a wide range of interagency professionals, global partners, and members of civil society to increase their awareness of irregular warfare threats, cross-fertilize often segregated activities, and develop holistic approaches to combat present and future irregular warfare challenges.