This chapter charts the complex relationship between the changing nature of state power and management of religious activism in Tunisia. In particular, it provides insight into a unique situation in the Arab world where, for the first time, jihadist ideologies and democratic experience intermingled, arousing greater passions, hopes, and fears. For a brief moment, Tunisia became the theater to test the political and ideational impact of democratization on antisystemic groups with jihadist ideological visions. The chapter examines the novelty of this case and provides insights on the factors that affected and mediated jihadist interactions with both the Islamist Ennahda-led government and other groups with opposing moral and ideological stances. Such an analysis of intrajihadi dynamics, jihadi-regime dynamics, and intergroup dynamics with other social and political actors helps elucidate the choice of strategies that jihadists adopted and how those choices were deeply affected by their own internal contradictions and ambiguities.