At 10.51 hours on 27 May 1942 the unescorted Jack (Master Serge Burrack) was hit by one torpedo from U-558 about 100 miles southwest of Port Salut, Haiti. The torpedo struck on the starboard side between the foremast and #2 hold. The explosion opened a large hole in the hull, blew the hatch covers off, stopped the engines, and damaged the radio, the starboard lifeboat and a raft. The ship sank quickly within four minutes and the suction swamped the port lifeboat, which had been successfully launched. The badly damaged starboard boat was launched with two men. 14 survivors transferred into this boat from a raft. These survivors were picked up by USS Grunion (SS 216) on 31 May and landed at the submarine base in Coco Solo on 3 June, after the submarine conducted a fruitless search for other survivors. Two armed guards and five crew members spent 32 days on a raft before being picked up. Five others on a makeshift raft were never seen again.

27 crew members, three armed guards and seven passengers of her complement of 43 crew members, nine armed guards and eight passengers (US Army personnel) were lost, including the master.