The Arab Spring defied Western theoretical assumptions that the Arab Middle East was incapable of political change through popular uprisings. Reflecting on historical and structural causes, this chapter identifies requisite conditions for political transitions in post-revolution states, with Tunisia as a case study. Despite successes (a new constitution, a non-partisan technocratic government, and general elections), Tunisian democracy remains endangered by broader regional issues: ideological struggles between reformists and former regime figures, the rise of political Islam and its radical offshoots, problems systemic to ailing economies, and difficulties in reforming discredited security forces. Yet, social and economic inequalities are most likely to derail the transition, with any unequal society in this unsettled region, more likely to squander democratic gains, oscillate between political regimes, and suffer substantial continued volatility.