Son of Gas Company Secretary, John Harper Penney, and his wife, Meggie Isabella Gilliers, Herbert Gillies Penney joined the High School at the age of 12.

He was one of 10 children, of which three brothers (Herbert Gillies, John Stanley and Reginald Harper) attended the High School and served in the war.

Herbert entered the High School (along with his older brother William Alexander Penney) on 11-Sep-1897, and left in July 1900 to work in an insurance office.

He joined the Royal Garrison Artillery volunteer force, and was made 2nd Lieutenant on 23-Jun-1906. On 1-Apr-1908, Lieutenant Herbert Penney was appointed to the 4th Durham (Howitzer) Battery of the 4th Northumbrian (County of Durham) Howitzer Brigade.

By 1911, Herbert was a fire surveyor and agent inspector in the insurance business.

He served as Captain with the Northumberland Fusiliers and the Dorset Regiment, joining the action in France on 12-Mar-1916.

Herbert was injured, brought home and honourably discharged, receiving the Silver Star on 23-Mar-1918, at which time he was living in Ealing Common, London.

After the war, he is believed to have continued in the insurance business in Glasgow, however he is believed to have died in Croydon on 21-Aug-1966.