Al-Shabaab is Al-Qaeda’s East African franchise and is in the midst of a diffuse ten-year insurgency against the United Nations-backed Federal Government of Somalia and the African Union Mission in Somalia (AMISOM). Consistent with its ultra-violent expansionist jihadist vision of an Islamic caliphate, al-Shabaab has in recent years grown into a transnational actor determined and able to orchestrate sensational and horrific terrorist incidents outside of the contours of Somalia. Al-Shabaab has been characterized as fiscal-military state. It has adapted an innovative and resilient funding model which has allowed the organization to sustain itself over the long haul, despite the loss of significant territory or the removal of key leadership figures. The United States has devoted significant resources to training and equipping AMISOM troop contributing nations and to identifying and directly targeting key leaders within Al-Shabaab. This paper argues that a necessary component of any successful effort to permanently cripple and ultimately defeat the organization will require a concerted whole-of-government effort to uncover and comprehend the al-Shabaab financial apparatus and to dismantle that operation. Cutting off al-Shabaab’s money flow will not alone achieve victory over the organization, however, without doing so, victory is unobtainable.