It is often argued that third party conflict resolution in the Caucasus has failed since the conflicts are not yet ripe for resolution, and due to the obstacles posed by the existence of unrecognised states. This chapter asks if such ‘ripeness’ can be created and it examines the solutions available in these extreme cases of separatist conflict. It finds that the timing of conflict resolution interacts with the process and substance of the approach. There is therefore room for creative diplomacy, but a viable strategy requires a multi-level approach which encompasses the international and the intra-communal level, including in the unrecognised states. Moreover, a solution needs to fudge the issue of sovereignty, and significant third party involvement is needed to make such a settlement both acceptable and sustainable.