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.

Episode 129 examines how Air Force Special Operations Command (AFSOC) is recalibrating for great-power competition while still answering today’s crisis-response and counter-VEO demands. Lieutenant General Michael E. Conley and Dr Kerry Chávez join the Irregular Warfare Podcast to unpack strategy, technology, and talent development at the sharp edge of irregular warfare.

Our guests begin by outlining AFSOC’s new strategic guidance—“Raise Air Commandos, Win Tonight’s Fight, and Sustain Relevance through Adaptation”—and describe how it builds on earlier reforms to balance crisis-response duties with preparation for peer competition. They then explore the “democratized skies” created by low-cost uncrewed aircraft systems, discussing implications for pallet-dropped drone swarms, counter-UAS, and agile acquisition. Finally, the conversation turns to force design and human capital, offering insights on cultivating Air Commandos who can integrate AI-enabled decision aids and out-cycle adversaries inside the OODA loop.

Lieutenant General Michael E. Conley is the Commander of Air Force Special Operations Command. A career special-operations aviator with more than 2,400 flight hours in the UH-1, MH-53, and CV-22, he has commanded at the squadron, wing, and combined-joint task-force levels and previously served as Special Assistant to the Chairman of the Joint Chiefs of Staff. His assignments have ranged from rescuing hostages to leading space-component forces, and his decorations include the Distinguished Service Medal and Bronze Star. As AFSOC’s chief, he oversees 20,800 Air Commandos and a $17 billion portfolio and champions “relevance through adaptation” to integrate SOF agility with Air Force mass.

Dr Kerry Chávez is an assistant professor in the Military & Strategic Studies Department at the U.S. Air Force Academy and an advisor to IWI’s Project Air & Space Power. She is also a two-time nonresident research fellow with the Modern War Institute at West Point and a fellow with the Institute for Global Affairs. Her work blends political science and data science to analyze emerging military technologies; she curates the MONSTr dataset on U.S. operations with novel capabilities and a pioneering global database of non-state-actor drone adoption. Dr Chávez regularly briefs DoD and industry leaders on counter-UAS strategy, synthetic data methods, and technology governance.