At the time of the Great War, Herbert's father, Thomas, owned what was probably Stockport major firm of household furniture removers. The family lived at 97 Shaw Heath, then a very well-to-do suburb. Herbert had attended Brentnall Street School and, at the age of 10, had won a scholarship to Stockport Grammar School. He was a keen sportsman and, whilst at the Grammar School, captained the cricket and football teams. This did not impede his academic studies and he was successful in gaining an Exhibition Scholarship to Christ's College, Cambridge. He started at the University in October 1913 but left as soon as War was declared in August 1914 and joined the army. By October, he had been commissioned as a 2nd Lieutenant and was promoted to Lieutenant in April 1915.
The following month, he was back in Stockport on leave for a few days before returning to the battalion to make final preparations for it to go overseas. They landed in France in mid-July, spending some time familiarising themselves with the reality of trench warfare. Over the following weeks, they alternated between periods in reserve and tours of duty in the front line south of the Belgian town of Ypres (now Ieper).
On 30 September, they relieved the 6th Sherwood Foresters in the front line at a position known as Chester Farm, some 5 kilometres south of Ypres. The Battalion's War Diary records that over the next few days there was considerable fire from enemy trench mortars and snipers.
Sometime during the night of 4/5th October, Harold was shot. His Captain wrote to the family explaining what happened. "He was with his platoon in the firing line and a stray bullet struck him in the neck and severed his jugular vein. He only exclaimed "I'm gone" and fell back unconscious and passed away a few minutes later, quite peacefully and quite prepared to meet his God. We, of course, did what we could for him, but it was of no avail and you will now he passed away with almost a smile on his dear old face. He was one of the best officers in the Regiment and the post he was holding was a most important and dangerous one. I put him in charge of it knowing that no Bosches would surprise him, as he had got his platoon in fighting trim, simply because he did not know what fear was."
The Colonel commanding the Battalion also wrote "I very much regret to inform you your son was shot late last night while on duty in the trenches. He was shot in the neck and expired immediately. There was no suffering. He died a noble death. We shall all miss your son very much, both as an officer and comrade, as he was a great favourite in the Battalion. We laid him to rest in an orchard quite close to one of our temporary headquarters, where also rest many other heroes of various ranks."
Finally, the Chaplain also wrote "I feel I must write to express my deepest sympathy in the great loss which has come to you. This afternoon, I buried him in the little Cemetery near the spot where he was killed. The Colonel of his Regiment, the Second in Command and Adjutant and other officers and men were present......Only a few days before, he and another officer dined with us in the chaplains' mess, it was such a pleasure to have him with us......"