About 09.00 hours on 16 July 1942 the unescorted and unarmed Gertrude (Master Walter Broward Crosland) was ordered to stop by U-166 about 30 miles northeast of Havana, Cuba. The crew was asked to abandon ship and they left immediately in a 14-foot motorboat. U-166 then sank the trawler by gunfire or by a scuttling charge. The motorboat with the crew ran out of fuel before reaching shore and drifted for 78 hours before being spotted by a Civil Air Patrol aircraft about three miles south of Alligator Reef Lighthouse. A boat out of Whale Harbor brought the three men ashore.