Dowling became executive officer on HMS "Naiad" when the ship was commissioned in 1940. Following service with the British Home Fleet, the cruiser transferred to the Mediterranean Station in May 1941, where she took part in the Battle of Crete. She was involved in action against German torpedo boats on the night of 20/21 May. On 22 May, after engaging a German destroyer with , "Naiad" was severely damaged by air attack. Following repairs, she became flagship of the 15th Cruiser Squadron and conducted shore bombardments in support of Allied troops during the Syrian campaign in June and July. She also escorted convoys resupplying Malta. In December, "Naiad" participated in the First Battle of Sirte against Italian naval forces. On 11 March 1942, she was torpedoed by a German U-boat off the Egyptian coast, and sank in just over twenty minutes. Dowling remained in the water for an hour and a half before being rescued by a destroyer.