Third place winner of the MacArthur Military Leadership Writing Competition for the CGSC class of 2006-001. This paper explores the ramifications of insurgency waged via strategic information warfare, especially focusing on its implications for Army transformation and operations. The nature of fourth-generation warfare collapses the traditional tactical, operational and strategic levels of warfare to such a degree that kinetic attacks such as IEDs with limited tactical effect have wide-reaching strategic impact. Fourth generation insurgency can only succeed by defeating allied political will. A war that thus hinges on strategic information forces military leaders, however well intentioned, to "target" their domestic publics as they counter and preempt enemy information operations. It therefore vital to have military leaders intellectually and culturally equipped to manage such conflicts without jeopardizing American values and democracy. Unfortunately, current military transformation efforts are not aligned with the needs of fourth-generation warfare. Rather than focusing on technological enablers, we must transform the very culture of our officer corps. In order to meet the challenges of destratified fourth-generation warfare, the officer corps must: Deemphasize kinetic solutions. Produce empowered, diverse, and critical thinking officers and soldiers. Increase pre-commissioning demands and rethink the philosophy of PME. Reintroduce rigor, challenge, and selectivity to officer careers. Defeat the problem of positivism by encouraging bottom-up innovation and the revaluation of military expertise. Unshackle officer assignments (and promotions) from branch constraints. These suggestions are designed to shift the culture of the officer corps from one increasingly out of step with the needs of fourth-generation conflict to one able to meet the challenges of evolving information war.