KG 55's units began a last minute withdrawal to the Eastern borders of the Reich in preparation for Hitler's war on the Soviet Union. I. Gruppe, III. Gruppe and the Geschwaderstab moved from their respective bases to Zamość in Poland, while III Gruppe were located to Klemensow aerodrome south east of Lublin in Poland. On 8 March 1941 the Erganzungstaffel was formed into IV. Gruppe, but was deployed to Dijon in France and remained there until 4 May 1944. KG 55 was to provide air support for Army Group South attacking into the Ukraine in its drive toward the Caucasus and the Soviet oil fields.
The opening day of the campaign resulted in the loss of seven aircraft. The next day a 8./KG 55 Heinkel was shot down by flak over Luck, the crew bailed out but were later found by advancing German forces to have been shot in the head. Two of the men were found at the local Commissar's house. The Luftwaffe established air superiority after destroying and capturing over 4,000 Soviet aircraft in the first weeks of the invasion (this figure rose to 21,200 by December 1941). Losses in the Kampfgruppen had also been heavy. The vast expanse of the front, the wear and tear of machines constantly advancing eastward took its toll. By August 1941 KG 4, KG 27, KG 53 and KG 55 were reduced to just 128 serviceable aircraft between them. The Geschwader played an instrumental role in the Battle of Kiev, in which the Wehrmacht effectively destroyed three Soviet Armies, killing or capturing 600,000 Red Army soldiers. I./KG 55 was credited with the destruction of 58 railway cars, 675 trucks and 22 tanks in this battle alone.
During the stalemate trough the severe winter of 1941/42 the units of KG 55 were redeployed to rest in Western France, not to return until April 1942 (with the exception of IV. Gruppe). KG 55 once again was deployed to the Ukraine to support the 11th Army in the Crimea, and the 6th Army pushing eastward from the Charkow area into the Caucasus. During the night of the 23/24 August the unit took part in the 'maximum' effort attack on Stalingrad which destroyed the centre of the city; one Heinkel was lost.
Disaster struck the German 6th Army at Stalingrad, for on 18 November the Russians counter-attacked and cut off the 6th Army. Hermann Göring assured Hitler that 'his Luftwaffe' could airlift in supplies. Göring wrongly believed a Heinkel that could carry 2000 kg of explosives could as easily carry 2000 kg of cargo. The Junkers Ju 52 and Heinkel 111's bore the brunt of Göring's supply plan. The Germans resisted fiercely but on 14 January 1943 Pitomnik airfield was captured by the Soviets and many supplies were then parachuted in. The last German elements surrendered on 2 February. KG 55 contributed only a small fraction of the meagre 90 tonnes of supplies the German 6. Armee received daily. Over 165 He 111's were lost over Stalingrad, KG 55's losses were 59. The Geschwader flew in 3,296 tons of supplies including 1,541 tons of food and 768 tons of ammunition, and 1,110 tons of fuel. KG 55 also evacuated 9,028 wounded soldiers.
KG 55 covered the retreat of the German forces until the spring and II./KG 55 celebrated their 10,000 mission on 11 May 1943.
KG 55 supported German forces throughout 1943, and was heavily involved in Operation Citadel and continued to cover the retreat across Russia. As air superiority slipped away, losses in the bomber units began to climb. Ritterkreuz des Eisernen Kreuzes holder Oberfeldwebel Willi Nemitz and Oberleutnant Herman Meyer of Stab II./KG 55 were killed in the space of three weeks in May 1943. Many of the Heinkels were modified to enable them to carry out low strike missions in the face of enemy air superiority. The specialist train-busting unit 14.(Eis)/KG 55 had its Heinkels fitted with an electric altimeter that enabled them to fly at tree top level over the railway tracks and began using the Ju 88C-6 aircraft in this role. The unit lost nine aircraft but flew over 5,000 missions before disbanding on 27 April 1945.
The role of the unit in Russia continued much as in 1943. Most notable during this year was the completion of KG 55's 50,000th mission on 10 May 1944. With production of the Heinkel ceasing in 1944 the unit was being prepared to re-equip with ground attack versions of the FW 190. KG 55 was mostly disbanded in 1944 with only 14.(Eis)/KG 55 surviving into 1945.
Luftwaffe records reveal the unit had flown 54,272 combat sorties, dropped 60,938 tons of bombs, carried 7,514 tons of supplies, and lost 710 killed and 747 missing from 1 September 1939 to 1 October 1944.
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