We hope that this edited volume will provide the audiences with an informed perspective about the significance of the Russian invasion and annexation of Crimea in 2014. It should not only enrich our understanding of the geopolitical implications of this development but also better contextualize the ongoing war in Ukraine. When Russia set out to invade Ukraine in early 2022, many argued that it was the return of classic geopolitical conflict but perhaps it had never left in the first place. The annexation of Crimea was an important turning point in Russia's efforts to reclaim what it considers its “backyard.” It also arguably had precedent in the Chechen and Georgian wars. The international community's treatment of the war in Ukraine has significantly changed since 2014 but it is not a sure bet that it will be able to reverse Russian encroachments in its neighboring states. We hope that this edited volume will highlight some critical turning points and moments of failure by the international community in the wake of Russia's annexation of Crimea. It should also inform any policy considerations regarding the status of Crimea as well as a potential future settlement of the conflict between Ukraine and Russia. The conflict may be a protracted one but the prospects for peace, we hope, will emerge sooner rather than later.