The King of Scotland was resident in Kirkudbright in July 1457 & sent a vessel to the Isle of Man to explore.
In 1507 Thomas Earl of Derby led a raid on Kirkudbright by the Manxmen which inflicted much damage. The last phase of the curtain wall at Peel Castle was erected in reponse to the Scottish threat in the early 1500's.
Dumfries suffered repeated raids by the English - it was notably raided and burned in 1384, 1415, possibly 1483, 1547, 1549, and 1570. I wonder what part if any the Earls of Derby played in these raids.

According to legend, the residents of Bride "ate their pudding before their broth" so that they had eaten the most substantial part first if there was a Scottish raid & they had to rush off to fight, thus missing part of their meal.

In 1547 the town of Kirkudbright was under siege.