This article seeks to understand the current challenges to the Syrian Arab Republic at a crucial moment in its history. The West is tentatively extending its hand to Syria after years of diplomatic isolation, yet Syria remains closely tied to Iran. In the last two years, Syria witnessed security challenges by both domestic and foreign forces that the republic has not seen since the Islamist uprising from 1976 to 1982. Today’s security, political and economic challenges to Syria are examined through the lenses of the history of the country’s state formation as well as a that of the modern day players affecting the Syria’s moves upon the complicated chessboard of Middle Eastern politics. While Syria losses its stamina in the fight against Israel, it is caught between a delicate vise-grip of intricate alliance with Iran and several rounds of sanctions by the US.