In the historiography of the Russian Civil War, the Rostov armed uprising of November 26 — December 3, 1917, remains a little-studied episode, although it was the first major clash between the Bolsheviks and organized forces of the counterrevolution in southern Russia. This article attempts a comprehensive analysis of the conflict based on a comparative study of Soviet and modern historiography, critical analysis of archival documents, the press, and newly introduced testimonies of participants. Particular attention is paid to a detailed reconstruction of events, which makes it possible to reconsider the established interpretations of the causes and dynamics of the uprising. The authors refute the widespread thesis that the uprising was provoked by a “Bolshevik ultimatum” to Ataman Kaledin, demonstrating that the armed action was a response to coercive measures by the Cossack authorities. The study shows that the harsh policy of Ataman Kaledin—expressed in the imposition of martial law, disarmament of units, and arrests—served as a catalyst for the consolidation of diverse revolutionary forces (Bolsheviks, Left Socialist Revolutionaries, and part of the Mensheviks) into a unified Regional Military-Revolutionary Committee. The article also analyzes the military-political reasons for the defeat of the insurgents, including the weakness of the Red Guards, the passivity of the garrison, tactical miscalculations by the command, and the destructive role of moderate socialists. The uprising is considered an important turning point that revealed divisions within the Cossack community and accelerated the formation of opposing camps at the beginning of the Civil War.