The rapid fall of the Ben Ali regime in Tunisia on January 14, 2011 has not only sparked a wave of uprisings across the Arab region, but has also raised many questions about the rotes of socio-economic inequality, youth unemployment, corruption, and government oppression in the making of the Tunisian uprisings. This paper argues that what seemed to be an island of stability in the region was in fact a ticking time bomb that was set off by Mohamed Bouazizi in December 2010. It further argues that the overthrow of the Ben Ali regime could not have taken place had it not been a leaderless revolt. As a result, the paper provides a critical analysis of the making of the Tunisian revolution by investigating the key factors that maintained stability, and the mechanisms that set the stage for the uprisings. In doing so, the analysis reveals the radical social transformation that took place since the early 1990s leading to the breakdown of the social contract, and the gradual drift of the middle class away from its implicit support of the Ben Ali regime. The new political landscape opens up a real opportunity for democratic transformation, vibrant civic engagement, and sustainable economic revival. Therefore, our analysis would be incomplete without a careful look at the new dynamic between the forces of political Islam, secularism, and the middle class. Finally, the paper closes with a summary and some concluding remarks.