Human smuggling is a complex process. Made up of actions both organized and chaotic, it compels migrants to deal with different structures and agents of power, among them smugglers, the state(s), and migrants’ own social networks. The current literature on human smuggling provides a detailed analysis of the different phases of this process, within which discussion of the structure and operation of this “business” can be situated. However, only minimal attention has been paid to migrants’ agency in the smuggling process. Engaging with recent perspectives in migration studies, which emphasize the need to conceptualize human smuggling by focusing on the interdependencies between the different actors involved, the analysis developed in this article aims to explore the different phases of the human smuggling process by focusing on the multilayered relations between smugglers and undocumented people. Drawing upon qualitative ethnographic fieldwork conducted with migrants on the Turkish-Iranian border, the article examines how the physical and sociopolitical conditions of border crossing affect people’s ways of thinking, behavior, and engagement with different structures of power. In doing so, the article attempts to further our understanding of how smuggled migrants mobilize their agency in such a way as to manipulate and challenge the system, as well as of how this process transforms migrants’ capacity to simultaneously recognize and unsettle state bordering practices.