Since the ouster of Tunisian president Zine El Abiding Ben Ali in 2011, the country’s borders have become more porous, allowing for increased unregulated trade and leading the government to present Kasserine, a province on the Algerian border, as a particular challenge to its efforts to establish the rule of law. Historically, Kasserine has borne the brunt of systematic socioeconomic marginalization traceable to the formation of the modern Tunisian state that ended up privileging the country’s coastal strip to the detriment of the interior regions. With high levels of poverty and unemployment and a dearth of state investments in socioeconomic infrastructures, some Kasserinians have turned to el contra, a label used by residents to refer to what the government calls “illegal smuggling,” along the Algerian border known as el-had as a source of employment and as a survival strategy. But with the 2013 rise of an armed insurgency in the nearby Chaambi mountains, media reports have portrayed the province as a hotbed of youth radicalization, conflating terrorism with smuggling, the lifeline of many impoverished families, and stigmatizing residents of the province (Meddeb 2015; 2016) by associating them with a state of illegality. By examining Kasserinians’ involvement in el contra, this paper aims to examine how the multiple and competing understandings of states of (il)legality and their attendant conditions of possibility are produced as well as disrupted at the geographical and conceptual margins of the state (Poole and Das 2004). Combining ethnographic research with media analysis, this paper asks: to what extent and in what ways do claims about and contestations over (il)legality and (its relationship to) “legitimate” citizenship constitute technologies of power and governance (Foucault 1975; Hibou 2006)? This work seeks to move away from analysis of smuggling through the optic of the resistance/compliance binary and to recognize the ways in which the very notions of legality and illegality constitute fields of contestation and are unstable and heterogeneous constructs undergirded by an ethics that need to be historicized (Roitman 2005).