2024 marks several anniversaries that constitute a watershed in the history of Cyprus - the 60th anniversary of the adoption of the first UN Security Council resolution on Cyprus and the deployment of the UN Force in Cyprus in 1964, the 50th anniversary of the 1974 events and the division of the island, and the 20th anniversary of the Annan Plan referenda and Cyprus's accession into the EU in 2004. Each has dramatically shaped the lives of Cypriots in all aspects, as well as the constructed polities on the island with repercussions that continue to prevail and sustain the status quo. In a world of uncertainty and in the face of alarming challenges faced by human societies, a critical reflection on these anniversaries is imperative to politicize the structural socio-political conditions that continuously reproduce an unsustainable status-quo, opening up space(s) to reimagine the future of Cyprus.