Much attention has been paid to the array of institutional mechanisms and political maneuvers Arab regimes employed to perpetuate power and modernize authoritarianism. While these pursuits shed light on formal state politics, they leave unexplored potentially consequential dynamics of contestation within society. Grasping these dynamics in their full complexity necessitates an investigation of less formal spaces and dispersed cultural practices that evolved outside formal politics and institutional contexts. Taking Tunisia as a case study, this paper contributes to our understanding of key dynamics that contributed to the Arab Spring by placing the recent developments within a broader cultural context marked by an apprehension toward a lived reality that has become impoverished in the absence of an engaging and meaningful form of citizenship. What is of particular interest are the ways in which the Arab authoritarian context favored the emergence of a “culture of contestation” that proved to be consequential over time. Locating contestatory dynamics at the intersection of the real and virtual world, this paper maps out cultural articulations of a changing state-society relationship. Focusing on the manifestation of a growing rift between authoritarian regimes characterized by exclusionary politics and an aspiring young population, it argues that the revolutionary momentum bespeaks an urge to revitalize the notion of citizenship. The claim for a reinvigorated form of citizenship is enmeshed with an awareness of and a public engagement with debates about individual and societal rights. Particularly important in nurturing this contentious spirit and contestatory culture are information and communication technologies. While initially providing a shielded free space of interaction, the Internet gradually evolved into an alternative arena of engagement among a seemingly depoliticized young generation that is capable of crystalizing dynamic sites of contestation and networks of activism. The focus on the political sociology of Internet use can yield a better understanding of how young people in a networked society develop an active civil culture that enables them to renegotiate the congealed and delimited notion of citizenship in the absence of political freedoms. Significantly, what the case at hand reveals is that the desire among a segment of the population to renegotiate their relationship to the state helped reclaim the political sphere the regime sought to monopolize and manipulate. The attempt to reposition oneself from subjects to citizens not only helped redefine the terms of political action but also led to the reinvention of the category of the political.