Conwy Castle was not well maintained during the early 14th century and by 1321 a survey reported it was poorly equipped, with limited stores and suffering from leaking roofs and rotten timbers.
These problems persisted until Edward, the Black Prince, took over control of the castle in 1343.
Sir John Weston, his chamberlain, conducted repairs, building new stone support arches for the great hall and other parts of the castle.
After the death of the Black Prince, however, Conwy fell into neglect again.

At the end of the 14th century, the castle was used as a refuge by Richard II from the forces of his rival, Henry Bolingbroke.
On 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 Tudur and his brother Gwilym, cousins of Owain Glyndŵr, undertook a surprise attack on Conwy Castle.
Pretending to be carpenters repairing the castle, the two gained entry, killed the two watchmen on duty and took control of the fortress.
Welsh rebels then attacked and captured the rest of the walled town.
The brothers held out for around three months, before negotiating a surrender; as part of this agreement the pair were given a royal pardon by Henry.

During the War of the Roses between 1455 and 1485, fought by the rival factions of the Lancastrians and the Yorkists, Conwy was reinforced but played little part in the fighting.
Henry VIII conducted restoration work in the 1520s and 1530s, during which time the castle was being used as a prison, a depot and as a potential residence for visitors.
Conwy Castle was not well maintained during the early 14th century and by 1321 a survey reported it was poorly equipped, with limited stores and suffering from leaking roofs and rotten timbers. These problems persisted until Edward, the Black Prince, took over control of the castle in 1343. Sir John Weston, his chamberlain, conducted repairs, building new stone support arches for the great hall and other parts of the castle. After the death of the Black Prince, however, Conwy fell into neglect again.
At the end of the 14th century, the castle was used as a refuge by Richard II from the forces of his rival, Henry Bolingbroke. On 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 Tudur and his brother Gwilym, cousins of Owain Glyndŵr, undertook a surprise attack on Conwy Castle. Pretending to be carpenters repairing the castle, the two gained entry, killed the two watchmen on duty and took control of the fortress. Welsh rebels then attacked and captured the rest of the walled town. The brothers held out for around three months, before negotiating a surrender; as part of this agreement the pair were given a royal pardon by Henry.
During the War of the Roses between 1455 and 1485, fought by the rival factions of the Lancastrians and the Yorkists, Conwy was reinforced but played little part in the fighting. Henry VIII conducted restoration work in the 1520s and 1530s, during which time the castle was being used as a prison, a depot and as a potential residence for visitors.
Conwy Castle