The Battle of Attu began on 11 May 1943 with U.S. landings on Attu Island. On 21 May 1943, with the situation on Attu deteriorating, the Japanese Imperial General Headquarters decided to evacuate the isolated garrison on Kiska. On 24 May 1943, "I-169" set out from Yokosuka bound for Kiska with a cargo of 1,440 rifles with ammunition and 2 tons of food. En route, she was ordered to join "I-171" and "I-175" in forming a scouting line in the vicinity of Attu. On 30 May 1943, combat operations on Attu ended with the annihilation of the Japanese garrison. "I-169" conducted a reconnaissance of Kuluk Bay on the northeastern coast of Adak Island on 5 June 1943, and on 9 June 1943 arrived at Kiska and discharged her cargo. Embarking 60 passengers, she departed Kiska on 10 June 1943. She survived an attack by a radar-equipped destroyer that opened fire on her with guns while she was on the surface charging her batteries and arrived safely at Paramushiro on 14 June 1943. On 14–15 June 1943 she took aboard cargo from the auxiliary submarine tender and refueled from "Teiyō Maru".