What happens when the world’s ‘oldest profession’ interacts with history’s oldest form of war? In the Horn of Africa, a symbiotic relationship between prostitutes and terrorists has emerged, illuminating critical information about the group’s ideology and strategy. In this article, we argue that al-Shabaab’s differential treatment of Somali and other East African women reveals the group’s strategic focus on Somalia, despite its claims to be a globally focused Islamic extremist organization. Through original ethnographic fieldwork in Kenya, the authors explore al-Shabaab’s deliberate relationships with different groups of women and explain how this helps scholars better understand the group. This article suggests the next phase of scholarship on gender and terrorism, encouraging scholars not only to pay attention to the relationship between women and terrorist groups, but to also examine the nuanced relationships between different categories of women and terrorist groups.