Harold Albert Montgomery was born at Ballarat in 1894 and at the time he enlisted was living at 212 Clarendon St., East Melbourne, more well known as Clarendon Terrace. He enlisted on 8 September, 1916. He was twenty two years old, 5' 8" in height, with brown hair and blue eyes, a motor mechanic by trade, with scars on his right thigh and jaw. Having given his father as next of kin on his enlistment form, he had crossed out his original entry and his next of kin is listed as his wife, V.M. Montgomery.

He embarked on 22 December 1916 on board the Persic A.34, landing at Devonport, England on 31/3/1917. On 7 April 1917, he left camp and went A.W.O.L. On his return, he was charged with disobedience of orders, gambling and being absent from camp and forfeited 4 days pay. On 11 April, he was admitted to hosipita; at Bulford, suffering from venereal disease. He was 27 days in hospital, finally discharged from Bulford  before rejoining his troop, the Auxiliary Australian Mechanical Transport Division,  at Camp Parkhouse.

On 20 June 1917, they was sent to France via Southampton, marching in to No.2 Command Depot and from here, to join the war effort. However, Howard Montgomery's time at war was short. on 20 June, 1918, he was sent back to England and discharged from service on 21 June 1918.  he returned to Australia on the Gaika, and went back to East Melbourne. on 8 June 1924, he was living at 157 Gipps St.

On 11 April, 1917, his father had written to the army authoities: "I wish to know if he has made any money allotment to his sister Constance Alice Montgomery, also in who's (sic) favour he has made his will."  The reply was that Harold would have the will, but his stipend of 5/-  had been assigned to a best male friend.

On 9 August, 1918, his father again wrote to the army authotiries enquiring whether his son had returned to Australia. The return letter said: '... according to the records, No 13071, Driver H.A. Montgomery,2nd Section, 1st Australian Auxiliary Mechanical Transport Company, rteurned to Australia on 5/7/1918 and is at present an inmate of No 11 Australian General Hospital, Caulfield, Victoria.'

Harold Alfred Montgomery was awarded the British War Medal, the Star and the Victory Medal.