Cyprus occupies an unenviable position among a group of intractable international conflicts which transcend their national borders and whose resolution has eluded third-party mediation. The Cyprus dispute has preoccupied theorists and practitioners of conflict resolution ever since the United Nations stationed its peacekeeping force on the island in 1964. Even attempts by the United Nations to revitalise the Cyprus talks following the 2004 referendum on the Annan plan have not yielded satisfactory results. For decades, the Cyprus problem has challenged conventional international analysis and defied traditional approaches to negotiation and peacemaking. This article grapples with the question of why this conflict has not been resolved despite endless negotiations. By extrapolating three seemingly distinct variables—Cypriotisation, Europeanisation and post-Kemalism—this article alludes to changes in the conflict's contextual parameters that are conducive to a political settlement.