Military historians have traditionally depicted the Ottoman’s second siege of Habsburg Vienna and the disastrous, ‘Great Turkish War’ that followed (1683–99) as a decisive victory that saved Europe and triggered Ottoman decline. But what gets lost in this historiography is the extent to which the war profoundly altered the confessional and ethnic make-up of the Ottoman army. The recurring defection of Ottoman Orthodox Christian warrior populations like the Serbs to rival armies, followed by Muslim retribution against them, constituted a sea-change in the nature of Ottoman imperial sovereignty and social relations on the ground. Not only would Istanbul henceforth bar Christian warriors from serving in the army; it was forced to outsource imperial governance and defence to pastoral Muslim warrior populations like Albanians on unprecedented levels. The Ottoman state, however, lacked both the resources and the will to pay and offer them sufficient access to status and power, which meant that these new agents of empire were difficult to control. This chapter sketches the nature and repertoire of violence and crime stemming from Istanbul’s massive privatisation of military and policing powers and its deleterious impact on inter-confessional and inter-ethnic relations in Ottoman society.