This paper tackles an important counterfactual question. Despite invasion, occupation, and frequent threats from multiple neighboring countries, why did Kuwait not develop a more capable national military? After all, the Kuwaiti military in 2020 is not significantly different from the military that the Iraqi Army attacked in August 1990. The conventional answer is that small states cannot defend themselves and therefore seek out external protection. But consider other small states like Eritrea, Rwanda, and Jordan--but particularly the United Arab Emirates--and this answer is incomplete. Kuwaiti society has been on the frontline of the region’s most wrenching wars, yet it has neither developed military capacities to deploy beyond its borders nor built any particular military capacity. Why? The staring assumption of this paper is that national militaries (preparation for war) are not just reactions to external conditions but are part of ongoing social and political dynamics. Moreover, building military capacity can come in multiple forms and may emerge from “wasteful spending” or be embedded in networks of rent seeking (i.e., the US military). First, this paper will present comparative evidence to establish the post-1990 history of Kuwait’s military. It will focus on changes since 1990, particularly Kuwait’s deepening relationship with the US military, as well as continuities since. An implicit comparison will be made with other Gulf Arab militaries over the same period. Second, the paper turns to explanation, weighing resident international relations theories against domestic and transnational political economy approaches. Given restrictions on research, the aim is to build a conceptual and methodological frame that will inform the field research in 2021-22. If field research in Kuwait is possible sooner, the paper can extend beyond the conceptual and begin to offer qualitative evidence to compliment the historical overview. The contributions of this paper fall in two broad areas. First, the field of critical security studies privileges analysis of transnational political economies and this paper enhances that work. Second in scholarship particular to Kuwaiti politics, there is a tendency to scope analysis into a seamless web linking parliamentary politics, rents, and corruption. Is it possible that these forms of resource distribution in Kuwait inhibit or supplant military “investment” or military rent-seeking? It may be the case that there are few incentives to build a more capable military in Kuwait but missing the constraints may make one blind to important politics at the core of what constitutes “security.”