Iran is encountering difficulties in its immediate neighborhood, whether in its relations with the Taliban government in Afghanistan or its relations with Azerbaijan. President Ebrahim Raisi’s regional diplomacy has not had an immediate effect on the strained relations with the country’s neighbors to the north. We have even observed a destabilization of the northern border of Iran during recent years. The northern border, which was an island of stability from the end of the First Nagorno-Karabakh War in 1994 until the war of 2020, is now an area of tension directly threatening the maintenance of stability in the border regions within Iranian territory. The period of stability was particularly important for the Iranian authorities, as the western border suffered the consequences of the Gulf conflict and US military invasions of Iraq in 1991 and 2003. During the same period, the eastern border was destabilized on two occasions: during the takeover of power by the Taliban in 1996 and following the US military intervention in Afghanistan in 2001. From Tehran’s point of view, since 2020, the dire security situation in the South Caucasus is due to the rising influence of regional rivals such as Turkiye or foes such as Israel and their respective alliances with Azerbaijan. The discourse on rising external influences is key to explaining the lack of reform in Iran’s regional policy toward the South Caucasus, despite the perception of a new Turkish challenge in this area. Indeed, this region was a Russian-Iranian sphere of influence for many years and Turkiye was unable to take a grip on it until after the fall of the Soviet Union in 1991. The Iranian discourse on the role of external actors is therefore a confession regarding the failure of its policy in the South Caucasus. Tehran was unable to limit the rise of Turkish and Israeli influence in what it considers as its “near abroad.” Since 2020, there has been a risk of destabilization of the northern provinces of Iran because of the tensions between Azerbaijan and Iran. This largely explains the increase in military exercises by the Islamic Revolutionary Guard Corps in the northern regions of Iran. This is to show the priority given by the Iranian authorities to preserving the territorial integrity of the country, but also to send a message to Baku on its cooperation with Israel and to Ankara on its military cooperation with Azerbaijan. There is also, according to the Iranian perspective, the fear of pan-Turkism as a decisive factor in the deterioration of Iranian-Azerbaijani relations since 2020. The internal dispute in Iran has placed the question of minorities at the center of the problem of the survival of the Iranian political system and the presence of an Azerbaijani minority in the northwestern provinces of Iran. This fear is fueled by the participation of members of the Turkish-speaking community in Iran in the protests of the fall of 2022 following the death of Mahsa Amini. In other words, in a phase of national protests and popular discontent, the authorities’ fear of destabilization of the country by the periphery has increased. Also, since 2020, the geopolitical context having changed, Iran has refrained from supporting Armenia, recognizing Baku’s legitimate right to recover its territorial integrity, which had been violated by the Armenian forces in Nagorno-Karabakh. Thus, the ceasefire of November 2020 led Tehran to consider the lasting installation, on the northern flank of its border, of a Turkish-Azerbaijani presence and the reduction of length in the Iranian-Armenian border. Moreover, Ankara, as a strategic military partner of Azerbaijan, has taken part in the fighting against the Armenians. The Second Nagorno-Karabakh War in 2020 not only played a crucial role in the development of Turkish influence, but also in Israeli-Azerbaijani relations. This new geopolitical configuration also led to a rapid deterioration in relations between Iran and Azerbaijan, although the development of economic exchanges remains a hurdle to the risk of military escalation.A conventional war against Azerbaijan is being considered by Iranian military strategists as a possible scenario over the coming years. What has been announced by the official Iranian media is greater support for Armenia in the event of a new confrontation between Armenia and Azerbaijan. This explains why, according to some Western sources, Iran might be using drones to monitor the border area and even delivering them to Armenia, which Yerevan denies. Azerbaijan’s victory in the Second Nagorno-Karabakh War inevitably changed the strategic environment, with Iran now in an unfavorable position. Beyond its posture as a failed mediator in the South Caucasus, Iran will likely seek to intensify its diplomatic and commercial ties with Azerbaijan, which now controls Nagorno-Karabakh’s supply routes and also hopes to complete the Zangezur Corridor. On the other hand, Armenia remains a useful partner that offers new possibilities amid the waning Russian influence as a result of the Ukrainian war. Iran will probably not be able to seize this unprecedented opportunity in the South Caucasus. It wants to avoid becoming a power that is incapable of asserting an “independent” policy in a region that Tehran nevertheless considers as its “near abroad.” Turkiye, more than Russia, will eventually provoke a new geopolitical situation as a result of the decreasing Iranian influence in the South Caucasus region.