As a result of political miscalculations by insurgents and effective state repression – often with the support of external actors such as the US, Argentina or Chile – most Cold War insurgencies in Latin America were defeated. However, when from the mid-1980s onwards, and in particular after the end of the Cold War, military dictatorships fell, and the region democratized and returned to civilian rule, several insurgent groups persisted. This scenario in which ‘veteran”’ Cold War insurgents, capable of ‘holding out,’ were the dominant form of insurgent groups operating in post-Cold War Latin America was substantially transformed by the events of 9/11. The assessment of this transformation stands at the center of this chapter, which will analyze Latin America’s contemporary insurgency and terrorism landscape. Particularly, the new transnational quality and criminal dimension of the region’s post-9/11 insurgency/terrorism landscape as both a policy invention and political reality will be assessed.