On the night of 25-26 June Jackson was one of eighty-two Australian raiders who entered the German trenches. Engineers with the party blew up two bomb stores and five minutes later the party withdrew after causing considerable havoc, but as they crossed no man’s land they suffered casualties from enemy artillery fire. Jackson got back to his lines safely, handed over a prisoner, and immediately went back out into the heavy shell fire to assist in bringing in one of the thirteen wounded. He went out again and was assisting a sergeant to bring in another wounded man when his arm was blown off and the sergeant was knocked unconscious. Despite his terrible wounds Jackson returned to his lines and got assistance, then went out again to search for the sergeant and the wounded man he had been helping in. One of the men was located and escorted to safety and Jackson was then dispatched for treatment. His arm was amputated.