For more than a quarter-century, the Nagorno-Karabakh conflict has been one of the most important factors influencing the political map of the South Caucasus. On 12 May 1994, Nagorno-Karabakh, Armenia, and Azerbaijan signed a cease-fire agreement that ended military operations in the conflict zone and has been observed until recently. Negotiations for a peaceful settlement have been underway within the framework of the Organization for Security and Co-operation in Europe Minsk Group co-chaired by the USA, Russia, and France since 1992, but society and the elite in Armenia, Nagorno-Karabakh, and Azerbaijan remain largely unprepared for compromise. Considering the settlement process a zero-sum game, they have generally accused one another of escalating the conflict and of a lack of willingness to restore peace. Other countries and international organizations involved in the negotiations do not share a vision of the future and frequently pursue their own interests. Accordingly, the Karabakh conflict could remain unresolved for decades more. The aim of the paper is a general assessment of the current stage and dynamic of this conflict and the impact of new trends and old obstacles on the prospects for further settlement.