At 03.16 hours on 8 June 1942 the unescorted Pleasantville (Master Johan Wildhagen) was hit on the port side underneath the forward mast by one G7e torpedo from U-135 while steaming on a zigzag course at 9 knots about 200 miles northwest of Bermuda. The ship had left New York in a coastal convoy which was dispersed off Chesapeake Bay. Shortly after the crew and ten passengers (US Army engineers on transfer to North Africa) abandoned ship in three lifeboats, the ship was struck on the port side in the engine room by a coup de grâce at 03.46 hours and sank by the bow after 34 minutes. The third officer and one crew member were lost. The U-boat surfaced, questioned the men in two lifeboats and offered help, but it was declined by the first officer of the merchant, who had also ordered the passengers to throw their dogtags and other items that identified them as soldiers into the water before the U-boat approached.

Eight crew members and two passengers in one lifeboat were picked up in the afternoon on the next day by Chickasaw City in 34°36N/69°55W and landed in Port of Spain on 18 June. The 35 survivors in the remaining two boats were picked up on 11 June by Paderewski and landed at Trinidad.