In the meantime he had joined the British Army as an ensign on 27 October 1854 and been promoted to lieutenant. Posted to the Crimea, he had arrived during the latter part of the Siege of Sevastopol. He was later under fire at the Battle of the Chernaya and commanded the grenadiers of the 19th Regiment of Foot at the assault of the Redan on 8 September 1855. During the last engagement he was seriously wounded by a ball which through his left thigh, shattering the bone. Left lying on the ground, he was finally rescued, and recovered after six months' confinement to his camp stretcher. His courage was commended in a special despatch by Sir James Simpson and he became popularly known as 'Redan' Massy.