At 04.17 hours on 16 June 1942, U-87 fired one torpedo at the leading ship of convoy XB-25 northeast of Cape Cod during a gale and fired at 04.18 hours a second torpedo at another ship. Berger observed how the first hit and thought that the second missed, but apparently both hit Port Nicholson. At 04.21 hours, a spread of two torpedoes was fired which both hit Cherokee.

The Cherokee (Master Twiggs E. Brown) was struck by one torpedo on the port side under the bridge. The explosion lifted the vessel out of the water, destroyed the chart house and incoming water gave the ship a sharp list to port. The speed was increased and the rudder was turned hard right, but a second torpedo struck the port bow 90 seconds later, causing the ship to sink by the bow with a 60 degrees list to port within six minutes. The rough seas and the extreme list prevented the launching of lifeboats and only seven rafts were cut loose. The ship carried nine officers, 103 crew men, 11 armed guards (the ship was armed with one 4in, two .50cal and two .30cal guns) and 46 US Army passengers. Three officers, 62 crew men, one armed guard and 20 passengers died. 44 survivors were picked up by the American steam merchant Norlago and landed them at Provincetown, Massachusetts the same day. 39 others were picked up by USCGC Escanaba (WPG 77) which took them to Boston.