In 1390, d'Artois joined the Barbary Crusade led by Louis II, Duke of Bourbon. He subsequently joined Henry of Bolingbroke (the future Henry IV of England) in Lithuania, fighting with the Teutonic Knights. His exploits there brought him to the attention of John Waltham (the Lord High Treasurer under Richard II), who recruited him as a household esquire. In September 1392, d'Artois entered the employ of Richard II, and by 1394 he is known to have been high in the King's favour.