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The al-Shabaab Organization, also known as the Mujahidin Youth Movement (MYM), and its allies have been active opponents in undermining the United Nations (UN)-supported African Union (AU) peacekeeping forces, the fledging Somali Transitional Federal Government (TFG), and all the UN efforts to support the Somali people. Al-Shabaab’s use of the internet and its control of the local news media has resulted in its increased ability to disseminate its story to the Somali public, to sympathizers throughout the world, and to the greater Islamic community. It is able to accomplish its strategic communication campaign through the use of organic websites, publication of online magazines and newsletters, and through international press conferences and interviews. The authors of this monograph identify al-Shabaab’s strategic, operational, and tactical vulnerabilities organized according to four sources of national power: diplomatic, informational, military, and economic (DIME). After exploring the group’s inherent and apparent weaknesses, the authors then provide some suggestions on what efforts or capabilities may be leveraged in defeating and deterring the group. Such instruments do not have to be kinetic or military in nature, but can be diplomatic, economic, or persuasive. The authors concentrate on diplomatic and informational options and do not address the military or economic implications at this time.