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This paper examines Azerbaijan's decision to go to war in Nagorno-Karabakh in 2020. It aims to unveil the lessons Azerbaijan learned from the reaction of major regional actors in the South Caucasus to rising tensions in Armenian–Azerbaijani relations from the mid-2000s to the 2020 July border crisis. The paper argues that the consistent unresponsiveness of the international community emboldened Azerbaijan to proceed with its war preparations. It shows that Azerbaijan perceived the attitude of regional powers as inability and/or reluctance to interfere in the conflict, and this created a permissive environment for an all-out war. [ABSTRACT FROM AUTHOR]