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The 2004 UN mediation efforts under the UN Secretary General Kofi Annan were the biggest ever UN and international effort launched. The Annan plan was the most detailed UN plan ever prepared on the Cyprus issue and the only one ever put to the referendum of the two peoples. Why did the mediation efforts abruptly fail despite the existence of a ripe moment in Cyprus in 2004? The main goal of the article is to investigate the linkage between the ripe moment and BATNAs of the parties if third party intervention is to be successful. The interplay between the BATNA’s and ripe moment provides a good example of how this interplay can hamper the effectiveness of mediation efforts and ultimately have a negative influence on the peace process.The article pays particular attention to the asymmetrical negotiation power of the parties based on their BATNA’s and the role this plays in producing the ripe moment for mediation. Furthermore this article makes the following contributions to the ongoing theoretical discourse on peace negotiation. First, it provides empirical evidence of how the BATNA’s of the parties in the conflict can affect reaching to the ripe moment. The paper suggests a refinement to the concept of ripeness through more explanatory and predictive power that focuses on the reasons of ripeness that might motivate the parties to the conflict to mediation in order to end the conflict. Although many studies emphasize the importance of ripeness in peace negotiations, this study demonstrates a number of obstructing factors that make UN mediation in ethnic conflicts vulnerable to the regional/global developments in setting up the dynamics of ripeness. Even in cases when UN as mediator seems catching the time right for effective mediation, as in Cyprus case it is extremely difficult to surmount a barrier that is closely associated with the geo-strategic interests of regional and international actors and BATNAs of the sides in conflict. Within this context, this analysis necessitates to rethink the model for third party involvement in general and particular in the Cyprus conflict.