This article examines the relationship between advisors and linguists in the contemporary military advising mission and applies an emergent postmodern military culture theoretical framework. This project’s multimethod collected data from Iraq, documents, and interviews. The study reveals an intriguing and nuanced story about the deployment of advisors and linguists in the advising mission. This article defines the military advising mission including the major actors. The article then introduces the postmodern military culture theoretical framework and method. The findings report many themes including linguist selection and hiring processes, the importance of advisor–linguist relationships, the relevance of linguists’ backgrounds, linguists as full advisory team members, and the building blocks of successful advising sessions. Effective advisors work with linguists to deploy a Swiss Army knife of cultural tools including peacekeeper diplomat, warrior, subject matter expert, innovator, and others to accomplish the mission, which divulge broader changes indicative of an emergent postmodern military and culture.