 In November 1941, the 2nd Division participated in Operation Crusader and conducted offensive operations towards the Sidi Azeiz area. Kippenberger enjoyed early successes in this campaign, with his battalion engaged in several battles. At one stage, he responded to an attack in the battalion's rear with a frontal assault resulting in the capture of 300 prisoners. Later on the night of 25 November, along with the 18th Battalion, he was tasked with the night-time capture of Belhamed, a hill adjacent to Sidi Rezegh. As the units moved to its positions, he made a navigational error which resulted in his headquarters company becoming separated from the other companies of the battalion. It took him until daylight for him to re-establish contact with the remainder of the battalion which, when he located it, was in its expected position having taken the hill with few losses. He was wounded by machine gun fire when he carelessly exposed himself while assessing the battalion's situation. Evacuated to a dressing station, he was captured by elements of the 15th Panzer Division three days later. Still on Belhamed, the 20th Battalion was destroyed in a counterattack, an action observed by a distressed Kippenberger through field glasses.
