Rochester Castle built during Henry III's reign were never repaired; it has been suggested this was because by the 14th century, when considerable sums were being spent on repairs elsewhere in the castle, Rochester had fallen out of favour as a royal residence. As the castle's importance as a high-status residence waned, its role as a barracks and administrative centre came to the fore. The reign of Richard II (1377–1400) saw the investment of £500 in repairing the castle. This was in part in response to French raids on England's southern coast during the Hundred Years' War as England's fortunes in the
Conwy Castle 12 August 1399, after returning from Ireland, Richard made his way to the castle where he met Bolingbroke's emissary, Henry Percy, for negotiations. Percy swore in the chapel he would not harm the king. On 19 August, Richard surrendered to Percy at Flint Castle, promising to abdicate if his life were spared. The king was then taken to London and died later in captivity at Pontefract Castle. Henry Bolingbroke took the English throne to rule as Henry IV in 1400, but rebellion broke out in North Wales shortly afterwards under the leadership of Owain Glyndŵr. In March 1401, Rhys ap