Berkhamsted Castle was taken prisoner at the Battle of Poitiers. When the Black Prince fell ill following his campaigning in France, he retired to Berkhamsted and died there in 1376. Richard II inherited Berkamsted Castle in 1377; initially the use of it was given to his favourite, Robert de Vere and, after de Vere's fall from power and exile in 1388, to John Holland. Henry IV lived in the castle after he deposed Richard in 1400, and he used the property to detain rival applicants to the throne. During this period Geoffrey Chaucer, later famous for his "Canterbury Tales", oversaw renovation work
Castles and Town Walls of King Edward in Gwynedd to conduct negotiations with the king. Henry Percy took an oath in the castle chapel to protect the king if he agreed to leave the castle, but when Richard left he was promptly taken prisoner, and was taken away to die later in captivity at Pontefract Castle. Tensions between the Welsh and the English persisted and spilled over in 1400 with the outbreak of the Glyndŵr Rising. At the start of the conflict, Harlech's garrison was badly equipped, and Conwy had fallen into disrepair. Conwy Castle was taken at the start of the conflict by two Welsh brothers, who took