Focusing on the achievements and failures of the 2017 Crans-Montana negotiations, this study examines the research question of how and why the last talks failed to resolve the Cyprus issue. It argues that progress in the negotiations was hindered by the enduring mistrust between the community leaders and the inadequacy of their resolve to reach common ground by reconciling their respective differences about the security and guarantees issue. The study suggests the process that helped bring about the Northern Ireland Good Friday Agreement offers a practical and effective approach to compare with the case of a seemingly intractable situation such as the Cyprus problem. The Irish–British negotiations were open to and involved a wide range of parties including the government, civil society, and international stakeholders. Moreover, they benefited from the decision to set a firm deadline for the conclusion of the negotiations. The findings of this study stress that because the previous Cyprus talks lacked an inclusive and transparent negotiation process – one with stated deadlines complete with alternative scenarios in the event of a referendum – they failed to address the broad gap of trust between the two Cypriot communities.