This article examines how and why many contemporary US mainstream military advisors—as compared to Special Forces advisors—often work from a position of disadvantage when conducting unconventional advising missions. Post-9/11 deployments to Iraq and Afghanistan have caused the US military to adapt to myriad complexities, including a renewed need for the widespread execution of the unconventional military advising mission by the Special Forces and conventional units. Although Special Forces typically possessed both the organizational flexibility and historical knowledge and skills to successfully perform military advising, the conventional military experienced some strains as it adapted to this nontraditional mission. This empirical work examines how the US military changed to conduct military advising missions, with a special focus on conventional forces. US military mainstream advisors cultivated a multifaceted “Swiss Army knife” of advisory skills—including warrior, peacekeeper–diplomat, information age technology, leader, and other essential cultural tools—to conduct the unorthodox mission. As soldiers build Swiss Army knives of advisory skills, they produce ripples of cultural change in the armed forces, which indicates the emergence of a more sophisticated, postmodern US military culture.