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One of the most terrible and difficult to understand pages of the Second World War history is the death of the Red Army South-Western Front in the second half of September 1941. An attempt has been made to answer the question why the largest group of Soviet troops (the South-Western Front), not inferior to Army Group “South” in number and having a complete advantage in tanks, aviation and artillery, was defeated in defensive battles and encircled. The largest was the “cauldron” near Kyiv. The Red Army suffered gigantic losses: 665,000 soldiers and officers, the entire material and technical base of the front ended up in the Kiev “cauldron”. After the defeat near Kyiv, the way to Eastern Ukraine, Azov and Donbas was open. Scientific analysis of the events and understanding of the causes of the Kyiv disaster of 1941, their generalized, comprehensive assessment are relevant for the study of modern military history. There were many reasons for the tragedy of the South-Western Front. Among the main ones, the following have been highlighted: incorrect assessment of Germany’s strategic priorities at the initial stage of the war; unpreparedness for a defensive war on one’s own territory; the advantage of the enemy in the tactics of fighting; lack of coordination of actions between military branches; loss of command of troops at all levels, from the General Staff to corps and division commanders; wrong personnel policy, as a result of which unprofessional persons who met the “main” criterion, such as personal loyalty to Stalin, came to the leadership of the Red Army; gross mistakes of the command, incompetence and voluntarism in setting tasks on the part of the Headquarters of the Supreme High Command (the highest military leadership of the country), etc.