The Nagorno-Karabakh crisis has highlighted the deteriorating relationship between Armenia and Russia. To some, it has been a sobering reminder of the precarious nature of alliances in the face of geopolitical realities. The protracted arming conflict between Armenia and Azerbaijan in the disputed region of Nagorno-Karabakh – an autonomous region within Azerbaijan – has come to epitomize the power struggle between Moscow and the two neighboring Caucasus states. By drawing on its mediating role in the 1994 ceasefire, Russia sought to maintain a beneficial relationship with both countries by sending military personnel and equipment into the region. Yet, with the escalation of the conflict in 2020, Armenia has been forced to acknowledge its declining influence in Russia’s sphere of influence. Moscow levying economic sanctions against Yerevan due to its reliance on technological and military assistance from France and the United States- further solidifies this notion. Compounded by Armenia’s inability to supplement their military needs domestically or from its regional supporters, Yerevan’s efforts to exploit the rivalry between the US and Russia in the South Caucasus backfired, intensifying the crisis. The debilitating discord has precipitated further inter-regional tensions, reinforcing regional anxieties over Russia’s expanding sphere of influence. With Azerbaijan and Turkey’s military alliance, Russia has been brought into an awkward position, having to choose between long-term interests in the region and a loyal ally. The crisis in Nagorno-Karabakh has spotlighted the fragile state of Armenian-Russian relations. This has come at an opportune moment for the West, with the region becoming increasingly militarized. With closer scrutiny placed on Armenia’s alliance with Russia, the West can capitalize on the rift in order to gain greater influence over the Caucasus region.