Many things have changed since the first Karabakh war (1988–1994), when Armenia emerged victorious. However, the years leading up to the Second Karabakh war in 2020 show that, in the long term, Yerevan lost out on many opportunities owing to the events that unfolded during the first war. At a time when Azerbaijan and Georgia were actively engaged in state and economy building following the fall of the Soviet Union, Armenia became sidelined from most regional economic projects. This has negatively impacted its economy, which is lagging behind those of Azerbaijan and Georgia, and resulted in significant outmigration from the country, thus reducing its population. While joint projects enabled Tbilisi and Baku to become closer and break free of Russian influence, the opposite was true for Armenia. Yerevan had to rely on Russia in many areas, including economic and military. War broke out between Armenia and Azerbaijan once again in 2020; however, this time it was Azerbaijan, using new strategies and new weapons, most notably drones that allowed it to recapture territory occupied by the Armenian armed forces. Now the war is over, there is a glimpse of hope for peace, and the United States can play the role of facilitator, as it did for Israel and Egypt during the Camp David Accords (1979). The Armenian economy needs to recover, and peace can start from there if Baku can be convinced to offer a helping hand to Yerevan and the latter to accept that help. However, there remain many other issues to be resolved before we can talk about cooperation; the most paramount being addressing Armenia’s irredentist claims and the preparedness of both societies for mutual acceptance of one another.