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At Liverpool Jackson swore his allegiance to the King and agreed to serve in the AIF, which is Australian Imperial Force
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Jackson was asigned for special duty in Alexandria and landed on Gallipoli on August 20 where he took part in the attack on Kaiajik Aghyl, the same day he arrived.
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On October 3rd,1915 Jackson was sent to a casualty clearing station, because he was suffering from diarrhoea and a problem with his teeth which made him unable to eat the hard rations that were being provided at that time on Gallipoli.
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Since Jackson was at the casualty clearing station he never got better so, He was placed onboard the Hospital Ship 'assaye'
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Three days out of the hospital, he was off-loaded and admitted to the 1st Auxiliary Hospital Cairo suffering from dysentery.
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After declaring himself fit Jackson left the hospital and rejoined his battalion
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Jacksons division took over a forward position in the eastern Armentieres sector, Relieving the 3rd Brigade, they had to do that as a prelude to the battle of the Somme.
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Jackson acted as a scout for a party that consisted of 40 Officers and men. they carried out a raid that had been planned by General W. Holmes on the forward trenches of the 231st Prussian reserve infantry regiment.
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During the raid Jackson captured one of the enemy and returned safely with him through the 400 yard No-Man's land to his own lines even through the intense barrage of enemy shell and machine gun fire
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When Jackson heard that some of the party had been hit, Jackson immediately returned into the enemy barrage and rescued one of his wounded comrades.
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On Jackson's second rescue mission he assisted Sergeant Hugh Alison Camden of the 19th Battalion to rescue seriously injured Private Alfred Edward Robinson.
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While Jackson was trying to rescue Robinson a blast from a exploding shell rendered sergeant Camden unconscious, and it blew off Jackson's right arm above the elbow, and inflicted further wounds to Robinson.
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After Jackson's injury he returned to his lines where an officer applied a tourniquet(compressing device) to his arm. Then believing that Camden and others was still in No-Man's land, Jackson search for half an hour until he satisfied himself that all the wounded had been brought in, and he was finally sent to hospital.
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The Hospital Ship 'St Patrick' took Jackson to England and at the 3rd London General Hospital the remainder of his right arm was amputated.
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Jackson he was transferred to the 1st Australian Auxiliary Hospital, which was established in the grounds of an estate.