NATO’s eastern flank in the Black Sea is a fractured security space that requires a special tailored approach. It is the Black Sea where Russia has chosen to test NATO’s resolve by the open use of force. The article argues that the transactionalist mode that Russia offers as a strategic basis for interaction with the West is not meeting the latter’s goals and interests. Recognised limitations of NATO’s “Tailored Forward Presence” in the Black Sea as compared to its “Enhanced Forward Presence”, diverging interests and polices of the allies, and Russia’s readiness to capitalise on these internal divisions are the critical problems interfering with NATO’s posture in the Black Sea.