[citation needed] However, in July 1914, he used his skills as a yachtsman for a quite different purpose, to surreptitiously assist his friend Erskine Childers (who was executed by the Free State government in 1922 during the Irish Civil War) in landing a consignment of weaponry at Howth aboard Childers' yacht, The Asgard, on behalf of the Irish Volunteers, an action which, had it become known, would have resulted in, at a minimum, the termination of Shephard's military career, if not far more drastic punishment.

[1] His covert operations came to an abrupt halt when he and a companion were briefly detained by the German authorities at Emden, after they were seen taking photographs in a sensitive area.

[2] On 22 August 1914, Shephard landed near Maubeuge for petrol, where he was given first-hand accounts of the fighting from French cavalry falling back from the Sambre canal.

On 24 August 1914, he and Lieutenant Ian Bonham-Carter reported to the Staff that General von Kluck's right wing would swamp the British Army unless the retreat was continued.

[5] Shepard's father, Sir Horatio, left a sum of money in trust to award annual prizes for essays on reconnaissance and related subjects submitted by RAF officers and airmen.