This article examines the current state of affairs in the Black Sea region by examining Ukrainian foreign policy and its implications on regional security. The focus is on Ukraine’s security dilemmas and regional priorities, which have gone through drastic changes after the country’s 2010 presidential elections. In order to meet Russian interests in the Black Sea region, the new Ukrainian government recently took some dramatic decisions. Among them, which were scandalously adopted by the Ukrainian parliament, was the president’s decision to refuse integration into NATO and to extend stationing of the Russian Black Sea Fleet in the Crimea. These and other issues are discussed in the article, and possible future scenarios in regional politics between the regional powers and the USA, EU, and NATO are also examined. The success of the European security architecture depends on the extent to which the regional and global powers can work to establish a functioning security system in the Black Sea region.