On 5 January 1941 he took command of the 30th Infantry Division, which participated in Operation Barbarossa. As part of Army Group North, the division prevented the breakthrough of a Soviet corps on the river Pola and then went on to counterattack. The battle lasted a week and Tippelskirch distinguished himself as commander of the division, he was awarded on 23 November, the Knight's Cross of the Iron Cross. In the winter of 1942, the 30th Infantry Division was encircled in the Demyansk Pocket, and Tippelskirch was ordered to be flown out. In August 1942, he was assigned as the liaison officer of the Italian 8th Army near the Don river. This position was extremely difficult for Tippelskirch because he had no German staff at his disposal and the Italians were reluctant to seek advice from German officers. The Italian 8th Army was sent into the Battle of Stalingrad at the end of the year. Tippelskirch was recalled from the front on February 1943. On 18 February 1943 Tippelskirch became the commanding general of the XII Army Corps. He retained this position until 4 June 1944, when he had to assume command of the 4th Army from General Gotthard Heinrici. Soon after, Operation Bagration against Army Group Center began on 22 June. The 4th Army was defending the Mogilev area and repeatedly requested permission to retreat. The approval came too late, but Tippelskirch along with most of the army managed to withdraw to behind the Dnieper, although 4th Army was still threatened by three Soviet fronts. The 4th Army was encircled east of Minsk on 1 July 1944, and most units of the army were forced to surrender on 8 July 1944. Tippelskirch himself was at the time outside the pocket and escaped capture. On 18 July 1944 he suffered severe injuries in a plane crash. On 30 July he received the Knight's Cross with Oak Leaves for his achievements in the fighting at Mogilev. On 31 October he entered back into service and replaced the ailing Otto von Knobelsdorff as the commander of the 1st Army in Lorraine. On 13 December of the same year, he took over as the commander of the 14th Army during the Italian campaign. He led the 14th Army until the end of February 1945. At the end of April 1945, Tippelskirch took command of the 21st Army in Mecklenburg and Brandenburg. On 29 April however, General Gotthard Heinrici now the commander of Army Group Vistula was dismissed, and Tippelskirch was ordered by Field Marshal Wilhelm Keitel to temporarily take over command of the army group. He reluctantly did so, taking the opportunity to negotiate with the Western Allies. He surrendered on 2 May 1945 in the Ludwigslust area to American forces.
