In 2020, the Azerbaijani army launched a massive attack on Armenian positions in Nagorno-Karabakh. After 44 days of fighting, Azerbaijan scored a major victory, forcing Armenian forces to retreat from the territories around Karabakh, followed by the deployment of Russian peacekeeping troops. While many analysts have focused on advanced technology to explain Azerbaijan's victory, this article argues that a comparative study of the First Karabakh War (1991–1994) and the Second Karabakh War (2020) points to differences at the strategic level, including political transitions, diplomatic policies, and military forecasts, to propose a comprehensive and strategic discussion of the two wars, away from technological determinism. [ABSTRACT FROM AUTHOR]