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General Collins had VII Corps attacking north, in the direction of Cherbourg (the largest port in Normandy and a major strategic objective) and west, toward the coast (in order to cut off the Germans in the Cotentin from their line of communications), but gains were limited and little progress could be expected until the bottleneck at Carentan had been broken. The task fell to the 101st.
General Taylor decided to attack from three directions simultaneously. The 327th Glider Infantry Regiment would come in from the north, the 501st from the northeast, while the 506th would undertake a night march, swinging around the almost surrounded Carentan to the southwest. Coordinated attacks were scheduled to begin at dawn, 0500, June 12.
Captain Sobel had seen to it that Easy Company had spent months of training at night. Forced night marches cross-country, through woods, night compass problems, every conceivable problem of troop movement and control of troops at night. The men were completely at ease working at night, indeed some of them insisted they could see better in the dark than in daylight.
According to Winters (who was by now the acting company commander,- Meehan was still listed as missing in action rather than KIA), the ones who could not handle the night were the regimental staff officers. They had "crapped out" on the training problems and had not done the field work night after night that the troops and junior line officers had undergone. It had shown up on D-Day night, Winters said: "They were the ones who had the problems getting oriented and finding their objectives. They had the big problem getting through hedgerows. The junior officers and enlisted men, completely on their own, had found their way around and found their objective with little problem and no maps."
The deficiency showed up again on the night march of June 11-12. F Company led the way, with E following. They set out for Carentan across a marsh, over a bridge, then west across fields to the railroad. It was rough going through swampy areas and hedgerows. The companies kept losing contact. F Company would hit a tough section, work its way through, then take off at a fast pace, with no consideration for the rear elements breaking through that same bottleneck. Regimental HQ kept changing orders for the boundaries of the 1st and 2nd Battalions. The companies would stop, dig in, set up machine-guns, then get orders to move out again.
There had been major fighting over the route the 2nd Battalion was following. The area was strewn with bodies, American and German, weapons and equipment, difficult to see clearly in the dark. Once over the Douve River, heading toward the railroad track, Easy lost contact with F Company. "I knew we would not be able to find our way to our objective over the strange terrain on our own," Lipton recalled, "and that we were strung out in a defenseless formation."
Winters tried to raise battalion on the radio. The operators spoke in muffled undertones. A German MG 42 (the best machine-gun in the world) opened up with several short bursts from somewhere off to the left. Lipton moved over to his machine-gunner and whispered to him to set up his gun facing toward the incoming fire. As Lipton moved quietly off to position the rest of his platoon, he remembered, "I almost jumped out of my skin when [the man] full-loaded his gun. The sound of a light machine-gun being full-loaded, two times pulling back and releasing the bolt, can be heard a half-mile away on a still night. All our attempts at being quiet and surprising the Germans gone for nothing." But there was no further attack, and Lipton breathed a bit easier.