During the past two decades, the ceasefire in Karabakh had been breached several times by the Armenian and Azerbaijani parties. The most significant cases of violation of truce are the relatively comprehensive military encounter in the course of the four days war of April 2016, the four days war of July 2020 and the latest conflict between the two sides starting from the morning of Sunday, September 27, 2020. The recent clashes in Karabakh are highly significant in terms of their extension and intensity, the volume of human and financial loses the level of preparedness, the curfew impositions and the general mobilization in Armenia and Azerbaijan as well as the all-out political and military support provided by the Turkish government and military to the Republic of Azerbaijan. Much of the recent fighting has concentrated along the border with Iran. This working paper analyzes the rationale behind the recent breakout of a long-expected military confrontation, the new dynamics to the old conflict as well as the role of Iran.