It is no surprise to come across information or video on social or mainstream media that was posted by a terrorist organisation like Al-Shabaab. In this regard, researchers have attempted to answer the question of what terrorist organisations aim to achieve by gaining a strong foothold in cyberspace. This article explores the evolution of Al-Shabaab in terms of their media usage and presence—from a local insurgency using magazines and radio stations, to what can be described as a media mogul in Africa. The author explores how and why this group chooses to pursue a strong cyber presence, and what, if anything, Africa and the international community can do about it.