The shift in the Nagorno-Karabakh conflict between Armenia and Azerbaijan in September 2023 has exposed the convergence of diverse strategic interests of both regional and extra must be understood within the context of a broader and more complex structure of alliances, involving great powers, such as the United States (U.S), Russia, Israel and the European Union (EU), as well as regional actors, including Türkiye and Iran. This article aims to shed light on the geopolitical shifts that led to Azerbaijan’s victory in September 2023. Throughout the article, it is demonstrated that the reversal compared to 1994 can be attributed to shifts in the external support for both sides. On one hand, Armenia lost its main security guarantor, namely Russia, prompting it to seek alternative support from the West and Iran. On the other, Azerbaijan consolidated essential backing from its key allies, Türkiye and Israel.