[4] He was attached to the 2nd Battalion, Oxfordshire and Buckinghamshire Light Infantry, then serving in India, from 13 March 1937, and subsequently transferred to that regiment 27 April 1938 (never joining the Indian Army) so that he would be able to continue his hobbies of tiger hunting and pig sticking.

Upon hearing of his brother John's death at the Second Battle of El Alamein in late 1942 with the 2nd Dragoon Guards, The Queen's Bays, Digby volunteered for the airborne forces and transferred to the Parachute Regiment.

His tiger hunting exploits were well known, and his reputation was enhanced as he was able to obtain the use of an American Dakota aeroplane in which he flew all the company officers in the camp to London for a party at the Ritz.

[1] Digby and A Company managed to travel 8 miles in 7 hours while also taking prisoner 150 German soldiers, including members of the SS.

During the battle, Digby wore his maroon beret instead of a helmet and waved his umbrella while walking about the defences despite heavy mortar fire.

When the Germans started using tanks to cross the bridge, Digby led a bayonet charge against them wearing a bowler hat.

[9] Because of his injury, Digby was sent to St Elizabeth's Hospital but escaped out of a window with his second-in-command, Captain Tony Frank, when the German nurses left them alone.

Wildeboer had a fake Dutch identity card made for Digby to allow him to pose as Peter Jensen, the deaf-mute son of a lawyer.

[8] He also wrote a report on the Battle of Arnhem Bridge that resulted in Lieutenant Jack Grayburn's posthumously receiving a promotion to captain and being awarded the Victoria Cross.

[10] After the war ended, Digby served in British-controlled Mandatory Palestine before being appointed to the 5th King's African Rifles in British Kenya in 1946, where he also bought two estates in Eburru and Nanyuki.