In WW2 the Germans got as far as Stalingrad in the south, and the Caucasus mountains, just north of Grozny. Leningrad was besieged in the north, & Moscow was not reached. Essentially Stalingrad was as far as the Germans got, at the end of 1942.
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The Germans' greatest defeat was at Stalingrad, and this changed the course of the war in Russia. The siege of Leningrad (as St Petersburg was then known) also resulted in defeat for the Germans, but if the latter had won the battle for Stalingrad they would also eventually have taken Leningrad, and then would have overrun the Soviet Union.
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The German invasion of the Soviet Union in 1941 succeeded in part because they attacked with no warning. The Soviet Union didn't have time to react to the German army's invasion.
The German invasion of the Soviet Union during WW2 was called Operation Barbarossa.
Stalin was surprised by the German invasion of the Soviet Union because he had signed a non-aggression pact with Germany, known as the Molotov-Ribbentrop Pact, and believed that Hitler would not attack.
Germany : Operation Barbarossa was the German invasion of Russia .