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Since the early nineties, the Black Sea region has witnessed fundamental geopolitical changes and significant shifts in its regional context and dynamics. In an attempt to react to the altered circumstances after the collapse of the Soviet Union and to address an increasing number of common challenges, the Black Sea states have jointed efforts in various regional cooperation activities. Throughout the years, the Black Sea cooperation has evolved with different speed and success, reflecting the difficult regional circumstances and attracting increasing external involvement. Today, more than twenty years after the first cooperation activities have been launched, the Black Sea cooperation is still shadowed by persisting historical rivalries, unrecognized territorial entities, ‘frozen conflicts’ and security threats. As a result, despite the many pressing problems of regional character, the cooperation efforts are currently showing rather limited outcomes. Seen against this background, the current paper presents a study of the main challenges and the existing potential for further development of the Black Sea regional cooperation.