As the forces that shape globalization and asymmetric warfare continue to influence how we think about and engage our adversaries, the US Air Force (USAF) must adapt its doctrine, training, and leader development to prepare Airmen for new challenges. To work in this new environment, Airmen of all ranks and disciplines must prepare for cross-cultural interactions. Recent studies have concentrated on the ground forces due to current operations that highlight the role of cultural competence in mission success. Our study examines the challenges to the Air Force that must underlie efforts to build education and training for cross-cultural competence (3C). We employed in-depth interviews to examine experiences in diverse international settings of a range of enlisted and officers at the diverse schools forming the Air University at Maxwell Air Force Base. Our goal was to understand the existing and changing nature of Air Force deployments and the concomitant challenges. Our findings revealed a number of settings and missions requiring a high degree of 3C and other missions and assignments for which a low degree of competence is suitable. We also analyzed the nature of the knowledge, skills and abilities being developed in the field as revealed in actual challenging situations for the Air Force in recent deployments.