On 24 November 1942, the evacuation of the 2/2nd Australian Independent Company from Timor along with 150 Portuguese people was approved by the Allied Land Forces Headquarters. In response to this, Commodore Cuthbert Pope, the Naval Officer-in-Charge Darwin, organised an operation utilizing HMA Ships Kuru, Castlemaine and Armidale. The operation was to involve the three ships undertaking two voyages each, the first to take place on the night of 30 November/1 December and involve a trip to Betano, Timor, in which the ships were to land 50 fresh Dutch guerrillas in the area along with supplies, and simultaneously withdraw 190 Dutch soldiers as well as the 150 Portuguese refugees. The second excursion was to be carried out on the night of 4/5 December, and entail the extraction of the 2/2nd Independent Company.
HMAS Armidale in Port Moresby harbour c. September 1942.
At 22:30 on 28 November 1942, Kuru set sail for Betano. Kuru was scheduled to arrive at approximately 20:30 on 30 November, where she was to unload the supplies on board and embark the Portuguese refugees, which were to transfer to Castlemaine once she arrived along with Armidale two hours later. However, Kuru hit bad weather during her voyage and arrived at Betano three hours late. Armidale—with two Dutch Army officers, 61 Netherlands East Indies troops and three Australian Army soldiers aboard—and Castlemaine set sail from Darwin at 01:42 on 29 November. At approximately 09:15 on 30 November, while 190 kilometres (100 nmi) from their destination, the two ships were attacked by a single Japanese aircraft. Having missed with several bombs, the aircraft flew off in the direction of Timor an hour later. Fearing that their discovery by this aircraft would jeopardise the mission, Castlemaine's Commanding Officer, Lieutenant Commander Philip Sullivan, ordered evasive action and signalled Darwin for further orders. A signal returned decreeing that the operation must proceed and a party of fighter aircraft were to be dispatched as protective cover.
Continuing in their voyage, Armidale and Castlemaine were attacked twice more by air, each time by a formation of bombers that bombed and machine-gunned the ships. Despite this, neither ship suffered damage or casualties and both arrived at Betano at 03:30 on 1 December, however there was no sign of Kuru. Having made sure that Kuru was not in the bay, the two corvettes decided to abandon the mission and sailed south in order to return to Darwin. Kuru's commanding officer, Lieutenant John Grant, had loaded 77 of the Portuguese refugees as well as one critically injured Australian soldier on board the ship and set sail at around 02:00 on 1 December from Betano, fearing he had missed the rendezvous with the other two ships. While approximately 110 kilometres (59 nmi) south of Betano, Armidale and Castlemaine sighted Kuru, and the three ships closed by dawn.
Following the transfer of passengers from Kuru to Castlemaine, the former received orders that she was to return to Betano that evening "and do the job tonight". At this time, a formation of Japanese aircraft was spotted and Kuru sailed for cover. Assessing the situation, Sullivan—as senior officer—decided that Armidale would accompany Kuru in order to unload the former's passengers at Betano while Castlemaine returned to Darwin. Armidale and Kuru assumed separate routes to Betano, and at approximately 13:00 Armidale was attacked by a party of five Japanese bombers; the explosives, however, fell wide of their target. At 13:58, Armidale reported that she was under attack from "nine bombers, four fighters" over the Arafura Sea.
Armidale undertook evasive action, manoeuvring frantically to avoid the aerial attack. However, at 15:15, the vessel was struck by two air-launched torpedoes, one hitting her port side and the other colliding with the engineering spaces, before a bomb exploded aft. Armidale listed sharply to port at this stage, and the order was given to abandon ship. As the crew leapt into the sea, they were strafed by the attacking aircraft. Sheean—after assisting to free a life-raft—was hit by two bullets from one of the aircraft, wounding him in the chest and back. Scrambling across the deck, he strapped himself into the aft Oerlikon 20 mm cannon and began shooting at the fighters in an effort to protect some of the sailors already in the sea. Subject to the fire from Sheean's Oerlikon, the Japanese aircraft were kept at bay and were unable to effectively strafe those in the water.
With Armidale rapidly sinking, Sheean continued to fire and managed to shoot down one of the Japanese bombers. He damaged a further two aircraft before Armidale's stern was engulfed by the sea. Despite this, Sheean maintained his fire as the water rose above his feet, and remained firing as he "disappeared beneath the waves". Sheean's crewmates later testified to witnessing tracers rising from beneath the water's surface as Sheean was dragged under.
There is a small geocoin for the FTF.