In light of Cyprus’ upcoming incorporation into the EU, this Paper approaches the Greece/Turkey/Cyprus security complex from a Greek and a Turkish perspective, respectively. The perceived Turkish threat has long been an obsession of Greek foreign policy. Although relations with Turkey have been improving recently and the Annan Plan for the reunification of Cyprus is endorsed by Greece, both Cypriot communities and parts of the Turkish establishment, this Paper does not paint an optimistic picture of the prospects of resolving the conflict. The lack of a solution for this conflict as well as Arab-Israeli conflict complicate closer sub-regional cooperation in the Eastern Mediterranean. From Turkey’s perspective, Cyprus’ accession implies that EU supports the Greek position on the Cyprus issue to the detriment of Turkey’s geo-strategic interests. In order to become a global actor, the EU is expected to eventually develop a security strategy for the Mediterranean and Black Sea region, with Turkey as an EU member at its centre. Turkey is likely to revise its Cyprus and Aegean policy only once membership becomes a credible option.