Abstract: Based on fieldwork over ten years in Iran and Cuba, this article follows the myriad political, economic, and cultural, relationships developed between Iran, Venezuela, and Cuba since 2008, as a direct challenge to U.S. sanctions on all three countries. What can we learn about U.S. sanctions when we look at the lived experiences of those both coping with and defying U.S. sanctions in three of the main targeted societies? What do these alliances of sanctions busting show us about the limits of U.S. sanctions, and about the further entrenchment of power by those at the forefront of political and military power in each of their respective states? This article explores the micro-social relations of those who have solidified this alliance, and explores what “sanctions busting” and building “resistance economies” mean for humanitarian and development issues.