Right before the regicide of Sultan Selim III in 1808, irregular warrior commanders-turned bandits who undermined security and imperial order throughout Rumeli, men like Kara Feyzî, his son Kara Feyzî-zâde ‘Alî Beğ, and their kith and kin, forced the sultanate to co-opt their transregional bandit enterprises as special forces charged with undermining Balkan national uprisings and terrorizing Ottoman subjects in Serbia, Montenegro and, later, Greece. It was these mobile terror and racketeering networks that played principal roles in inciting the Serbs into rebelling in the first place after their irregular warrior-janissary confederations conquered Belgrade from the Ottoman government in 1801. After visiting their terror and protection rackets onto both Muslim and Christian subjects across Rumeli for well over a decade, they “legitimately” refocused their terror, ransom-slavery, and pillaging campaigns against Serbs, Montenegrins, and Greeks throughout the reign of Sultan Mahmut II (r. 1808-1838), refashioning themselves as respectable “borderland warriors of faith.” This presentation explores Ottoman archival documents alongside Muslim as well as Serbian, Montenegrin, and Bulgarian narrative sources on the movements of Muslim families from the mountains of eastern Rumeli that Istanbul settled along new types of boundaries that began emerging between the Ottoman empire and Serbia during the First and Second Serbian Uprisings (1804-13 and 1815-7) as well as Greece during the Greek Revolution (1821-1829). Alongside these families, it also explores how their Christian counterparts, Serbian and Montenegrin leaders such as Đorđe Petrović (Karađorđević), Miloš Obrenović, and Petar Njegoš responded to this state-sponsored banditry, even though the state nominally recognized these Christian leaders as “representatives” of the sultan charged with maintaining order in their increasingly autonomous polities. I will argue that these Christian leaders, experienced as paramilitary leaders that aided Habsburg and Russian forces during wars against their Ottoman overlords, emulated the practices of their Muslim counterparts across the border by establishing their own racketeering operations that terrorized and enslaved Muslims locked in their new polities as well as other non-Serbian Christians like the Bulgarian, Vlach, and Greek warrior subjects who joined Muslim raids into Serbian territory. Hence, through these frequent conflicts, one begins to see how a culture of paramilitarism that spread through the intersection of competing imperial visions for the Balkans and local power struggles forever changed political imaginations in the region but ensured the enmity and mistrust among different groups within these new polities colonized social relations in ways they did in the Ottoman empire beforehand.