Views from the Cyber Trenches: Understanding U.S. Military Cyber Dynamics

In this special edition episode of Cache Me if You Can, we dive beneath the surface of the U.S. military’s cyber enterprise to uncover the hidden challenges facing today’s cyber warfighters. CSIS Deputy Director Lauryn Williams is joined by three retired cyber operators—Col. Sean Kern, LtCol Tony Siciliano, and Col. Ben Ring—for a candid conversation about the real conditions inside the cyber trenches. Drawing on anonymous quotes from current operators across the Services, the episode breaks down the four systemic pressures shaping the cyber workforce: Leadership: Why technically proficient cyber operators rarely rise into senior command roles. Training: How uneven and outdated training pipelines leave some operators unprepared for mission demands. Readiness: Why a small cadre of highly skilled “unicorn” operators end up carrying the majority of the operational load. Culture: How traditional service cultures undervalue cyber expertise compared to kinetic career fields. Together, the guests unpack how these structural issues weaken the nation’s cyber readiness—and why addressing them may require establishing a dedicated U.S. Cyber Force designed to recruit, train, and retain the country’s top cyber talent. Learn more at the CSIS Strategic Technologies Program.