Since 1976, Syria has suffered two separate but in nature similar rebellions which was different in terms of spreading, impact and size. The existing literature fails to compare these rebellions and answer the question on how two similar uprising can produce different outcomes. The objective of this study is to answer that question and produce a foundation that is usable when studying future uprisings in the Middle East and Syria. This is a qualitative research that uses multiple case studies that are compared in order to fulfil the objective of this study. The research if a desk study and uses an abductive approach. Two different theoretical concepts have been used in order to understand the dynamics that shaped the two rebellions. These are Frank H. Zimmerman's theory on why insurgencies fail and Frederick D. Miller's model of movement decline. The authors pinpoint different factors that makes a uprising prone to failure or success and these factors has been used as a lens when analysing the findings of this essay. The findings of this essay suggest that key differences that made an impact on the conflicts where the amount of local support, external support and the role of social media. In order to fully understand the dynamics that shapes modern rebellions, further research on the role of globalisation and social media is conflict must be conducted.