At 07.50 hours on 12 June 1942 the unescorted Cities Service Toledo (Master Kosti F. Toivola) was torpedoed by U-158 about 20 miles east of the Trinity Shoal Light Buoy in the Gulf of Mexico, while she proceeded on a nonevasive course. Two torpedoes struck two seconds apart on the starboard side amidships in the #6 and #7 tanks. The tanker rapidly took a starboard list. Five minutes later two more torpedoes struck the starboard side about amidships at the #4 and #5 tanks, causing the tanker to burst into flames. The armed guards (the ship was armed with one 5in, two .50cal and two .30cal guns) stayed with the ship as long as possible and fired three rounds at a light thought to be the U-boat. The most of the eight officers, 28 crewmen and nine armed guards abandoned ship in two lifeboats, because all rafts and the two other lifeboats were destroyed. One of these lifeboats could not get clear the flames and the men had to jump in the water. The Cities Service Toledo sank about two hours after the second attack. The 17 men in the remaining lifeboat were picked up by the Norwegian motor tanker Belinda several hours later. Eight hours after the attack, the surviving 13 men in the water were picked up by the American steam tanker Gulfking and the Panamanian steam merchant San Antonio. All survivors landed at Burwood, Louisiana and were then sent to New Orleans, where four men were hospitalized. One officer, ten crewmen and four armed guards died.