Following the September 11 attacks, Afghanistan, which became central to the U.S.’s ‘global war on terrorism’ doctrine, neither achieved the survival of its ‘fra-gile/weak state’ status nor was able to mitigate the security threats and risks that stemmed from Taliban fundamentalism, despite a wide range of missions and activities undertaken by the United Nations and NATO. This situation may be considered as the failure of the nation-state building project implemented by the U.S and the defeat of the international coalition forces after their 20 year long existence, as well as may be seen as the triumph of Taliban and its’ supporters. This article aims to shed light on ‘how the peace was lost’ in Afghanistan by focusing the internal and external dynamics behind Afghanistan’s long-term war fatigue. To reach this aim, this article takes into consideration domestic and foreign actors’ interests, objectives, and actions in the light of time and conjectural de-velopments. In this context, it problematizes the solution approaches which were brought to bear against the chronic security issues that cause history to repeat itself in Afghanis-tan.