A main objective of this article is to examine the underlying reasons behind the collapse of the reunification talks on Cyprus aimed at a federal model. Another aim of the article is to analyze Türkiye’s assertive policy in the Eastern Mediterranean. A major argument is that the disruption of the balance of power with respect to the Cyprus problem in favor of the Greek Cypriots after 2004 and the lack of a shared Cypriot identity were fundamental causes of the failure of the talks. The study also contends that the emergence of a siege mentality after the July 2016 coup plot in Türkiye, together with its economic and military strengthening, the rise of multi-polarity in international politics, and diminishing EU political sway in the country, incentivized Türkiye to pursue an active foreign policy agenda in the Eastern Mediterranean. This study concludes that the failure of long-standing negotiations to reach a federal settlement on the island and the comfortable position obtained by the Greek Cypriot Administration (GCA) in the negotiations vis-à-vis the Turkish side following the accession to the EU together with Türkiye’s nationalist posture after 2016 and the deepening of the identity dilemma among the Greek and Turkish Cypriots over the course of time induced Türkiye to shelve a federal solution to the Cyprus issue and return to a pre-2002 two-state solution. The article also concludes that Türkiye was further prompted to take an independent course in the Eastern Mediterranean by the combination of a number of factors: the rapprochement between the AKP Government and nationalist elements in the country after the 2016 coup plot, the militarization of its foreign policy, Türkiye’s perception that the West was in decline, the decreased credibility and thus leverage over Türkiye of EU political conditionality, Brussels’ shortcomings regarding a common security and foreign policy and the rise in Türkiye’s military and economic capabilities.