This article provides a comparative analysis of the legal grounds for the deployment of the Russian Armed Forces in a series of conflicts in the Caucasus, namely in the disengagement between North Ossetia and Ingushetia (1992–1994), South Ossetia/Georgia (1992–2008), Abkhazia/Georgia (1994–2008), and in the Russian–Georgian War of 2008. The difficulties in codifying certain actions from the point of view of international law are detailed. The article discusses whether the political and military actions of Moscow in various Caucasian conflicts were driven and interconnected by one and the same logic, or were purely ad hoc fixes. Cases where Russia’s actions have been legitimized by securing mandate from a regional intergovernmental organization are differentiated from cases where it has acted on the basis of intergovernmental agreements, as well as from the application in certain cases of Article 51 (“the right of individual or collective self-defence”) of the UN Charter. The legitimacy or illegitimacy of the deployment of the Russian Armed Forces abroad is considered in the context of, and in comparison with, a series of cases where force has been used in conflicts by coalitions under a UN mandate, as well as by NATO and some Western powers.