Its strategic importance in the Welsh Marches meant that it was destroyed and rebuilt a number of times until the early 14th century, when the area was largely pacified.

The de Boulers (later known as Bowdler) family held the castle until 1214, when it was destroyed by Prince Llywelyn ab Iorwerth of the Royal House of Aberffraw.

[2] The rebuilding of Montgomery Castle in stone was commenced in the late summer of 1223 on the 16th birthday of Henry III of England, a mile to the south-east of the original site.

[3] When the First English Civil War began in August 1642, Mid Wales was largely Royalist and the castle held for Charles I by the elderly Lord Herbert of Cherbury.

[6] Much of Wales rose again in the 1648 Second English Civil War and the castle walls were demolished by Parliament in June 1649, despite opposition from the 2nd Lord Herbert, who succeeded his father in 1648.