At 05.40 hours on 23 Oct 1942 the unescorted Reuben Tipton (Master Giles Warren Hatch) was torpedoed by U-129 about 400 miles northeast of Trinidad. One torpedo struck the starboard side in the #1 hold, blew off the hatch covers and buckled the deck. The engines were secured, the radio operator sent distress signals and the armed guards fired 20 rounds from the stern gun in the assumed direction of the U-boat without ever sighting it. As the ship settled by the head the master noticed that she could be saved, restarted the engines and proceeded towards the coast on a zigzag course with 3 knots.

The U-boat maneuvered into a new firing position and fired at 09.45 hours two other torpedoes that struck on the port side in the engine room and the #4 hold and caused the ship to sink within two minutes, killing one officer and two crewmen on watch below. The survivors of the nine officers, 35 crewmen and ten armed guards (the ship was armed with one 4in, four .50cal and two .30cal guns) abandoned ship in one lifeboat and a raft. The master and a crewman were picked up from a raft by a US Navy PBM flying boat after two days and taken to Trinidad. On 26 October, the remaining survivors were picked up by a British motor torpedo boat after being sighted by a patrol plane and landed at Barbados.