It is clear that Hector had by then already acquired at least a paper title to a large estate. When the Lords of the Association, a factious party of the nobility, took up arms against James III, Alexander of Kintail despatched his sons, Kenneth and Hector, with a retinue of 500, to join the Royal standard; but Kenneth, hearing of the death of his father on his arrival at Perth,returned home at the request of the Earl of Huntly; and the clan was led by Hector Roy to the battle of Sauchieburn, near Stirling. After the defeat of the Royal forces, and the death there in 1488 of the King himself, Hector, who narrowly escaped, returned to Ross-shire and took the stronghold of Redcastle, then held for the rebels by Rose of Kilravock, and placed a garrison in it. He then joined the Earl of Huntly and the clans in the north who were rising to avenge the death of His Majesty but meanwhile orders came from the youthful King James IV, who had been at the head of the conspirators, ordering the Northern chiefs to lay down their arms, and to submit to the powers that be.