In April 1941, the Division moved east via Warsaw and along the Vistula River to conduct intensive training in river and bunker assaults as well as training in combat in forested areas until the 6 June 1941, when they moved up to their assembly area near Hrubieszow on the River Bug. At 03.15 a.m. on the 22 June 1941 the assault over the river began achieving complete surprise over their Soviet opponents. However, the bunker complexes to the east of the river proved to be a difficult proposition to overcome only being finally subdued after considerable losses on the 23 June 1941.
The advance to the old Soviet-Polish border of 1939 was hampered by Soviet tank attacks on the 1 July 1941 near Dubno but once subdued, German Panzer forces raced on towards Zhitomir and Kiev. In the meantime the 44th Infanterie Division was assigned the task of supporting the flank and defending against continuous attacks from Soviet Partisans and Regular forces operating from within the Pripet Marshes. With this task completed the Division was assigned next with taking part in the assault on the city of Kiev in August. Meanwhile the 6th Army had by now also succeeded in crossing the Dnieper River near Gornostaipol north of Kiev. Whilst the panzer troops of both Army groups Centre and South were used to conduct a deep encirclement of Kiev, 44th Infanterie Division was utilised to divide and surround the Soviet forces in the city itself.
Fighting in the Beresani area lasted from the 20-30 September 1941 with retreating Soviet forces then being pursued over the Psel and Voskla Rivers to between Kharkov and Belgorod. However, the pursuit was hampered by the arrival of the autumn rainy season turning the roads into rivers of mud. By the beginning of November, the Division had been moved back into Army Reserve west of Kharkov but had to be used to plug a gap forming between the 297th and 298th Infanterie Divisions and then to take up defensive positions on the Donets River. Winter had now arrived and whilst hampered by the lack of adequate clothing and equipment the Division had to continually contend with constant attacks from the Soviet Winter Offensive. The whole German army was reeling from this offensive on a broad front and the decision was to shorten the lines and to defend more favourable positions and the 44th Infanterie Division was used to bolster the border of the 6th and 17th Armies following a Soviet breakthrough on both sides of Izyum on the 18 January 1942.