Operation Spider’s Web and the Future of Asymmetric Warfare

Episode 130 of the Irregular Warfare Podcast takes listeners inside Operation Spider’s Web—Ukraine’s bold campaign of long-range drone strikes targeting Russian military and industrial infrastructure.

Our guests begin by examining why Ukrainian defense planners opted for this unprecedented strike operation and how it was designed to disrupt Russian strategic depth. They then unpack the technical, operational, and strategic considerations that enabled the operation, including the role of commercial drones, asymmetric targeting, and irregular doctrine. The episode concludes with reflections on how Spider’s Web is reshaping our understanding of deep operations and irregular warfare in the 21st century.

Brigadier General Kip Kahler is the former Senior Defense Official and Defense Attaché to Ukraine, with over two decades of national service in strategic roles across the interagency and foreign militaries.

COL Brian Petit is a retired SF Army officer who teaches and consults on strategy, planning, special operations, and resistance. He is an adjunct for the Joint Special Operations University.

Kateryna Bondar is a fellow at the Center for Strategic and International Studies, and a former advisor to the Ukrainian government, where she led reforms in defense and innovation. Her article, entitled How Ukraine’s Operation “Spider’s Web” Redefines Asymmetric Warfare, serves as the anchor for episode 130.