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In previous decades, going back to the Korean War, the South Korean government used to send balloons carrying propaganda into North Korean territory. For the last decade, however, the South Korean government has not sent any balloons, but instead various private activist groups have done so on their own initiative. They have been using different kinds of hydrogen balloons, and more recently hexacopter drones, to carry political, religious, and/or humanitarian materials into North Korea. These non-state actors have a demonstrated interest in continuing to improve the delivery technology they use. We review open source reporting to assess the current technical state of their air vehicles and estimate, for example, how far they are likely to penetrate into North Korea. We draw comparisons to similar efforts—which were ostensibly by private organizations but actually funded by the CIA—to deliver propaganda by balloon across the Iron Curtain in Europe during the Cold War. We also consider some plausible ways in which the airborne delivery of contraband might improve as the technology available to non-state actors increases.