The secessionist entities that emerged out of the turbulent upheavals in the 1990s in the South Caucasus have, over many years and with enormous external assistance, successfully defied the jurisdiction of their metropolitan states. As entities that have attained a status of de facto statehood, they epitomize unresolved conflicts between core principles and doctrines in public international law. This study addresses the interplay between law and politics against this context and problematizes false dichotomies that have arguably hindered the transformation of these territorial disputes. The author devotes particular attention to different ways of engagement with the de facto states below the level of political endorsement.