At 05.26 hours on 2 November 1941 U-208 fired a spread of two G7e torpedoes from a rather long distance at the unescorted Larpool (Master Charles Patton) which was steaming at 8 knots in rough sea and strong wind about 150 miles east-southeast of Cape Race. The ship had been in station #91 of convoy ON-27, leading the outside starboard column, but experienced bad weather shortly after departure and eventually lost contact with convoy during the night of 28/29 October. One of the torpedoes hit her on port side forward after a running time of 5 minutes and 38 seconds, but had not much effect. Nevertheless, the 39 crew members and four gunners (the ship was armed with one 12pdr and two machine guns) immediately began to abandon ship, first releasing the rafts and then launching both lifeboats. The master had just put his personal papers in the port lifeboat in charge of the second officer when it drifted away as the painter had parted. He went to the other side and discovered that the starboard boat in charge of the chief officer had already pulled clear, shouting to them to bring it back alongside, but was surprised when the chief officer answered from the after deck. His lifeboat had been filled with water from the engine room discharge, so he and four other crewmen went aft to launch one of the small boats there and eventually abandoned ship together with the master, who ordered all boats to remain nearby in order to reboard her at daylight as he did not believe that she will sink. In the meantime, the U-boat moved closer and fired two more torpedoes as a coup de grâce from only 300 meters at 07.17 hours, that struck the drifting Larpool on port side amidships and at the bow, causing her to break in two and sink within 40 seconds.

As the master and chief officer were in the small boat, the starboard lifeboat with 15 occupants was left in charge of the third officer, while the remaining survivors were in the port lifeboat. All boats set sail and soon lost sight of each other, experiencing a very heavy westerly gale with strong wind, very rough sea and extremely cold temperatures. This probably led to the loss of the 19 crew members and three gunners in the second officer’s boat that was reported missing after being last seen by the boatswain on the day of the sinking. The small boat with six men only made little headway, in fact one day there were blown back about 50 miles, but they kept heading for the south of Newfoundland and eventually made landfall near Burin on 10 November. Four crew members died of exposure in the third officer’s boat before ten crew members and one gunner were rescued by HMCS Bittersweet (K 182) (A/LtCdr J.A. Woods, RCNR) after 13 days at sea and landed at Halifax. All survivors suffered severely from exposure, thirst and swollen feed from the icy water in the half-filled boats.