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
Clan Ramsay was claimed by the Douglases who became jealous and William Douglas, Lord of Liddesdale captured Alexander Ramsay with a strong force of men, imprisoning him in Hermitage Castle, where he was starved to death. Alexander's brother, William Ramsay, was captured by the English at the Battle of Neville's Cross but was not killed by them as he lived to tell the tale. In 1400 another Sir Alexander Ramsay held out in Dalhousie Castle against a siege by the English, who were forced to retreat due to Ramsay's resolute resistance. In 1513 during the Anglo-Scottish Wars, Sir Alexander's descendant, another Alexander