National borders exemplify a number of paradoxes: the boundary both separates and unites neighboring states. The border delimits and defines the state and its territory, and disputes in borderlands can eventually affect international relations and regional stability. In regions like the South Caucasus, where states are weak, there is a possibility for the conflicts of one country to flow over into neighboring countries, and for states to become entangled with conflicts there. This article explores how the form of such cross-border conflict dynamics relates to the character of the two states in question. This is done through the comparative analysis of Georgia's cross-border contacts with Russia, including the present situation in the separatist entities of Abkhazia and South Ossetia. The case of the Russia-Georgia divide is important for challenging traditional explanations of foreign policy and for learning possible ways to de-escalate dangerous cross-border conflicts.