At 00.37 hours on 29 Nov, 1942, U-161 fired a spread of two torpedoes at the Tjileboet (Master J.W. Kroese), dispersed from convoy ON-145, and scored a hit after 72 seconds. The ship exploded in a heavy detonation and debris fell even around the U-boat in a distance of about 1000 metres. At 08.14 hours on 28 November, the Tjileboet had been spotted and she almost escaped as they forced the U-boat to dive at 11.10 hours when turning towards it and firing with artillery, but was finally hit after a difficult hunt in heavy rain squalls and being identified by her distress calls.