The recent political changes in the region, such as Russia’s annexation of Crimea and Moldova’s signature of an Association Agreement with the EU, have transformed the political context of the Transnistrian problem, ongoing for the past 20 years. The repositioning of the involved actors – Moldova, Russia, Transnistria, and Ukraine – in the context of these new political realities might be the key to breaking the deadlock surrounding this breakaway region. In this article, the author explores each actor’s evolving approaches to the problem and assesses how the problem could be resolved or exacerbated in the near future.