John Leslie Oakley enlisted at Chesterfield into Antrim Field Company RE in 1940, which in 1941 was redesignated as 591 (Antrim) Field Company RE. In May 1943 the company converted to a parachute role and joined 6 Airborne Division as 591 (Antrim) Parachute Squadron RE.Sapper Oakley qualified as a military parachutist on course 81 which ran at RAF Ringway from 9 to 16 September 1943. The course instructors’ notes record ‘good performance, confident and capable.'

He served served with as 591 (Antrim) Parachute Squadron RE until 1945 when he was posted to Palestine.