On 19 October 2014, US Air Force C-130 transport aircraft dropped 28 bundles of small arms and ammunition for Kurdish forces defending the Syrian city of Kobani from attack by the non-state armed group Islamic State (IS) (US, 2014a). IS claimed to have picked up at least one of the bundles and showed the seized shipment in a video posted on YouTube two days later (Rogin, 2014). The Pentagon confirmed that IS had intercepted one of the bundles (Simeone, 2014). This is not an isolated example of a state with robust transfer controls authorizing a risky delivery of small arms and ammunition to a non-state armed group in a volatile region of the world. This chapter explores such decisions— and their consequences—in relation to the Middle East and North Africa (MENA), a region with high levels of armed violence and political instability.