The Boswell family began their association with Auchinleck in 1504, when the Auchinleck family ceased to have a male heir. King James IV granted the estate and title to Thomas Boswell when he married the daughter of Sir John Auchinleck; Thomas Boswell then became the first Laird Auchinleck. The fortunes of the barony rose and fell. When the 6th Laird Auchinleck, David Boswell (1640-1712), assumed the estate from his uncle, David Boswell, there were many financial and legal burdens. He sold some of its land and carefully managed what remained. By the time he disponed the barony to his eldest son, James Boswell (ca. 1675-1749), circa 1702, he had reduced its debts considerably. Under the stewardship of James Boswell and his wife, Lady Elizabeth Bruce, they cleared the estate’s debts and began increasing land holdings. The standing of the barony reached its pinnacle under Alexander Boswell (1707-1782), the 8th Laird Auchinleck. He, too, increased land holdings and succeeded in buying back most of the lands that had been sold by his grandfather, David Boswell. With James Boswell (1740-1795) as 9th Laird Auchinleck, the estate again fell into disorder. His son, Sir Alexander Boswell (1775-1822), 1st Baronet Auchinleck, increased the estate’s size by purchasing the neighboring barony of Ochiltree. However, his finances had declined by the time he died from an injury sustained in a duel. The barony never regained the prominence it held under the 8th Laird Auchinleck, Alexander Boswell. By the time James Boswell gave Auchinleck House to the Scottish Historic Buildings Trust in 1986, it was in disrepair.