The Black Sea is of strategic importance not only to regional but also increasingly to the global security. Despite the increasing importance of the region, the strategies enumerated by key state players remain unchanged, with patrolling, posturing, and exercises being the main pillars of security. NATO based its strategy on forward presence and readiness, presented as means for deterrence against threats. The annexation of Crimea has proven Russian strategy of territorial pursuit as more successful than Euro-Atlantic partnership programmes. This gap could be addressed with strategy generation in hypothetical scenarios, leading to more representative discussion over security in the Black Sea. To provide the testbed for strategies, a wargaming concept is proposed, which can simulate the dynamic environment and key players.