Harold Kipling was the son of Frank and Isabella C Kipling, of Richmond, Yorkshire, and husband of Mary Mainland Kipling. He enlisted into the Army 3 June 1943.

Harold volunteered for airborne forces while serving in The Royal Army Service Corps during World War II, and later qualified as a military parachutist on Course 84, which ran at RAF Ringway from 20 September to 1 October 1943. His jump instructor noted this about Harold's performance:

"Steady, intelligent and made rapid progress"

He subsequently served with the 12th (Yorkshire) Parachute Battalion and took part in the parachute drops into Normandy in June 1944 to seize Ranville from the Germans. Harold was killed later in the month by enemy shellfire while the battalion was in a rest area in Ranville.

Pte Harold Kipling died on 17 June 1944, aged 32 years, and is now buried at Ranville War Cemetery, Calvados, Normandy.