Other Memories Having gained a reputation for "unusual capacity for imparting enthusiasm as well as for organization", he was relieved of the command of Desron 10 on April 8, 1943, to lead the new Destroyer and Destroyer Escort (DD-DE) Shakedown Task Force that was being organized at Bermuda to systematically work up newly built destroyers and destroyer escorts before they joined the Atlantic Fleet.
Arriving at Bermuda on April 13 aboard the destroyer tender Hamul, Holloway quickly established an efficient arena for drilling untrained crews in operations at sea. When newly commissioned ships arrived at Bermuda, their officers and men debarked for training aboard Hamul and ashore while their vessels underwent inspection and repair by task force staff. Ships then returned to sea to practice tactics and the use of their equipment, in daylight and in darkness, against towed surface targets and "tame" submarines. Task force staff handled all repairs and logistics, freeing commanding officers to focus solely on training their crews.
At first, Holloway's training program only covered destroyer escorts and a few gunboats, but his "Bermuda college" was so successful that it was expanded in September to encompass all newly built destroyers, and would eventually be extended to Canadian and British vessels as well. By the time of his relief on November 14, 99 destroyer escorts and 20 destroyers had already graduated from the program and 25 other ships were being trained. The shakedown period had been reduced from six to eight weeks of haphazard preparation to only four weeks for destroyer escorts and five weeks for destroyers, with vastly superior quality of training. For this success, Holloway was awarded the Legion of Merit, whose citation commended his having "built up an efficient organization, turning over to the Fleet competent seagoing vessels and thoroughly indoctrinated personnel. His conspicuous success in fulfilling this important assignment and his skill in collaboration with other commands have contributed vitally to the effective prosecution of the war."