This article examines the political and military activities of the Khwarazmshahs in Azerbaijan during the late twelfth and early thirteenth centuries, with particular emphasis on the campaigns and governance of Jalal al-Din Khwarazmshah. The study employs a historical-critical and contextual methodology based on primary medieval sources and relevant regional scholarship. Political and military developments are analyzed alongside administrative practices and their socio-economic impact on the local population. The article situates Khwarazmshah expansion within the broader context of Seljuk fragmentation, regional feudal rivalry, and the Mongol threat, highlighting Azerbaijan’s strategic significance during this transitional period. Special attention is given to key regions such as Tabriz and Nakhchivan, where Jalal al-Din attempted to establish a new political center following the collapse of Khwarazmshah authority in Central Asia. The findings demonstrate that although Jalal al-Din’s rule in Azerbaijan was short-lived, his military campaigns and administrative policies significantly affected the region’s political stability and social structure, contributing to the conditions that facilitated subsequent Mongol domination. By adopting a region-centered perspective, this study offers a reassessment of Khwarazmshah rule in Azerbaijan and contributes to the historiography of medieval Caucasia on the eve of the Mongol invasions.