This thesis analyses the problematic trajectory of the Syrian Revolution 2011, which was inspired by the Arab Spring. It first evaluates the causes of the revolution during Bashar al-Asad's era. An era was aimed to be a transition from authoritarianism to democracy and from suppression to fair openness. It second investigates the factors behind turning the Arab Spring into a Syrian winter, plunging the country into internal war and uncontrolled violence. The research is based on a qualitative approach that includes interviews as a source of information and analysis. Factors covered are the disintegration of Syrian society as the greatest challenge for the civil uprising and mass mobilization as well as the regime's coherent inner core accounting for the regime's violence and persistence. As violence breeds violence, the revolutionaries decided to react violently towards the regime brutality descending the country into an internal war. The formulation of the Free Syrian Army was formalized, but could not transform into a proper military formation, and so could not control the spread of violence in the country. The inclination towards Jihad was evident and common, and associated with resorting to violence because the revolutionaries are Muslims, and believed in Jihad as a way to defend themselves and their families. However, Jihad became more formalized with the arrival of global Jihadists to Syria, forming Jihadist groups and controlling parts of Syria. The stance of the international community was another big obstacle helped escalating, but not terminating the conflict. A conflict could develop into a devastating regional crisis changing the structure of the Middle East and changing the international politics of this vital region.