At 20.10 hours on 22 May 1942 the unescorted and unarmed Plow City (Master George Hazeleaf) was hit by one torpedo from U-588 about 200 miles off Cape May, New Jersey. At 15.00 hours, the ship had spotted the sail of a lifeboat from Peisander, which had been sunk by U-653 (Feiler) on 17 May, but the master suspected an U-boat and fled the area on a zigzag course at eight knots. The U-boat had noticed the smoke and chased the ship for four hours before firing a spread of two torpedoes. The first missed by about five feet ahead and the second struck on the port side aft of the #2 hold at the waterline. The second mate was blown overboard by the explosion and drowned. The watch below secured the engines and the most of the eight officers and 23 crewmen abandoned ship in two lifeboats, while the radio operator stayed behind to send distress messages. At 20.22 hours, a coup de grâce hit the engine room on the starboard side and caused the ship to sink by the stern within three minutes.

One survivor was taken aboard the U-boat for questioning and the Germans returned him along with rations of cigarettes and rum to one of the lifeboats. They also rightened one of the boats that capsized during launching before leaving the area. The survivors were picked up after five days by the American patrol yacht USS Sapphire (PYc 2).