This paper will explore the phenomenon of highway-robbery in the context of the Trabzon-Erzurum-Bayezid road during the second half of the nineteenth century and early twentieth century. It will argue that the existence of better roads not only increased the state’s ability to control its territories, but also that of the highway-robbers to challenge the state’s authority. In the Trabzon-Erzurum region, there were a variety of actors who resorted to highway-robbery: fugitive soldiers, members of the Hamidian regiments, tobacco smugglers, and tribesmen. These people were not marginal members of the Ottoman society, but products of modern state institutions such as universal conscription, integrated market economy, commercialized agriculture, and sedentarization. Highway-robbers also formed alliances with local power holders, leading to further conflicts between the gendarmerie and military units. In addition, the central government sought other ways of fighting against highway-robbery: introducing an insurance policy for postal services, increasing the sedentary population in the region, building more khans and police stations along the road, extending the right to carry guns to the general populace, and employing watchmen along the road. Ironically, these policies in particular and a better road network in general did not lead to increased levels of security in the region but to its further militarization.