This project examines the sophisticated cultural toolkit deployed by contemporary US military advisors to successfully build productive relationships with foreign security forces, advance the advising mission, and survive combat. This project's data stems from a three-part multi-method, including a survey conducted in Iraq; a document analysis; and interviews. This article focuses on numerous subthemes that coalesce to vividly divulge an intriguing story about how contemporary advisors build relationships with counterparts, including avoiding an "Ugly American" approach, how cross-cultural competence benefits the mission and increases survivability, learning about counterparts, the power of informal socializing, employing humor, navigating taboo topics, cultural stretching and associated limits, diplomatically balancing strength and subtlety, and taking physical and cultural risks. This project argues that effective advisors deploy a multifaceted cultural toolkit filled with peacekeeper-diplomat, warrior, subject matter expert, innovator, leader, and other tools, which reveals broader organizational changes indicative of emergent postmodern US military culture.