The Arab Spring brought optimism about the prospect of democratization in the region. However, transition toward democracy was often violent, prompting concerns about the price of freedom. While Egypt and Tunisia underwent smooth and relatively peaceful transition in ousting autocratic regimes, both Libya and Syria were devastated by violent confrontations. This Book examines four claimed prerequisites for peaceful transitions: the existence of civil society, degree of economic disparity, military loyalty to the regime, and the utilization of social media. A comparative country analysis is conducted to compare the various propositions in Egypt, Libya, Syria, Tunisia, and Yemen. An index table of peaceful transitions is developed. The book reveals that among the decisive factors contributing to violent or peaceful transition lies in the military’s loyalty to the regime and the level of economic disparity. Yet, the strength of civil society and the spread-out of Social media are significant aspects that can neutralize the regime’s coercive apparatuses.