The S-44 completed four war patrols and was on her fifth patrol when sunk. During her first patrol S-44 sunk a small freighter off the coast of New Britain. On her Second patrol she sank the Japanese gunboat Keijo Maru southwest of Florida Island. During her third war patrol, S-44 put four torpedoes into the heavy cruiser Kako and sent her to the bottom. Kako was one of the four cruisers who had participated in the first Battle of Savo Island, sinking four Allied cruisers without a single loss to themselves. S-44 damaged a destroyer type ship off the coast of New Georgia on her fourth patrol. S-44's first four war patrols were conducted in the Solomon Islands area.

S-44 began her fifth patrol out of Attu Island in the Kuriles. The first day out, she was forced to dive when a Japanese warplane dropped several depth charges. Nothing eventful happened for the next eleven days, but on the night of October 7, a radar contact was established on what was thought to be a small freighter. The S-44 proceeded to close on the surface and commenced firing her four-inch deck gun. The enemy ship, which turned out to be a destroyer type vessel, returned fire with all guns.

At this point, Captain Brown gave the order to submerge and sounded the diving alarm. The S-44 had taken major damage including a hit below the water line. A pillowcase was waved in hopes the destroyer would cease firing but she continued shooting, scoring several more hits. About eight men made it into the water before S-44 sank, but only two were picked up. These two men, Chief Torpedoman Ernest Duva and Radioman Third Class William Whitemore, were first interrogated at Ofuna and then placed in a forced labor group at the copper mines in Ashio. Both men survived the experience and were repatriated at the end of the war.

NOTE: I received an update from Mike & Pat - - William F. Whitemore was my Uncle and he died on Feb 20, 2026 - His son is living in California, His Grandson is at the Calif. Merchant Marine Academy.