“Black Headbands in the Highlands” is a focused and analytical historical analysis of the Chechen wars spanning from 1994-2009, focusing on the roles of non-state actors. It attempts to dissect the fragmentation of Chechen resistance forces as the conflict progressed, and why, if resistance fragmented, the conflict cycle continued and grew worse. It argues that leadership decapitation, economic devastation, and tactical devolution allowed non-native ideologically backed organizations to enter the conflict zone. In turn, the introduction of foreign, mainly radical Wahhabist organizations, lines of funding, and methods of support irreparably changed the nature of what, was at its core, a nationalist struggle. Simultaneously, the devolving battlefield helped shape the early narrative, method, and motivations of the, still young, international Jihadist organizations. Finally, the devolution of nationalist fervor, combined with the introduction of multipolar radical elements, championed by individual ‘middle management’ commanders, ensured a continuation of an already confusing and bloody conflict cycle. Black Headbands utilizes a chronological historical approach, broken into the first Russo-Chechen War (1994-1996), the interwar years (1996-1999), and the second Russo-Chechen War (2000-2009). Its sources are drawn from primary account of Russian, Chechen, and Arab fighters, field commanders, and politicians, as well as Western journalist accounts and articles. Scholarly work is sourced from American, European, Russian, and limited Chechen diasporic input. Although this work is geographically outside of the Middle East, it deserves consideration in that specific context. It is relevant to academic conversations regarding MENA. Radical Islamist organizations continue to be an extremely relevant non-state actor regarding conflict in the periphery of the Muslim world, and Chechnya is one of the first. Chechnya was the unfortunate location of two larger geopolitical happenstances (Russian decolonization, and global radical Islamism) butting against one another. Furthermore, analysis of non-state actors and their interaction with existing conflict locations deserve due deliberation.