Pringle was accepted by CDSNA as an allied family in July 2012.
The Douglas Archives state,
“One branch of the Pringles were the descendants of the family of Whitsome, Berwickshire, afterwards designed of Smailholm and Galashiels. Robert Hop Pringle of Whitsome is mentioned in a donation to the monastery of Soltray, confirmed by King Alexander III. For their support of the Bruce family, in their competition for the crown, the Pringles of Whitsome were deprived of their lands by King John Baliol, who conferred them upon John de L'yle, confirmed by a charter from King Edward 1 of England, l3th October 1295. After the battle of Bannockburn, the lands were restored to Reginald Hop Pringle of Whitsome, by charter from Robert Bruce in 1315. During the brief and shadowy sovereignty of Edward Baliol, after that monarch's death, by a mandate from King Edward III of England, they were ordered to be delivered up to "Walter de Insula," son of John de L'yle. They were restored, in 1336, to Thomas Hop Pringle of Whitsome, who, in 1363, had a safeguard to go into England, with his son and twelve persons in their retinue.
The Pringles of Whitsome were adherents of the house of Douglas, and held the office of scutifer, or squire, to the earls of that name. Robert Hop Pringle of Whitsome was present, in that capacity, with James, second earl of Douglas, at the battle of Otterbourne in 1388, where the earl was slain. From Archibald, third earl of Douglas, lord of Galloway, styled the Grim, he got a charter of the lands of Smailholm, Roxburghshire, in 1408, as well as a grant of the lands of Pilmuir and Blackchester in Lauderdale, which remained for nearly three centuries in possession of the family. From the Douglases also, who were then lords of Ettrick forest, he got the forest steadings of Galashiels and Mosalee, which were held by the Pringles in kindly tenants till the forfeiture of the Douglases in 1455. They were subsequently held by them as kindly tenants of the crown till 1587, when they were feudalized by charter and sasine. It was this Robert Pringle who built the tower of Smailholm, a large square building, now entirely ruinous, and originally a border keep, situated among a cluster of rocks on an eminence in the farm of Sandy-knowe. The apartments rise above one another in separate floors or stories, and mutually communicate by a narrow stair. A wall surrounds the building, enclosing an outer court, and being defended on three sides by precipice and morass, the tower is accessible only by a steep and rocky path on the west. At the farm of Sandy-knowe, which was leased by his paternal grandfather, Sir Walter Scott spent some years of his boyhood. In a note prefixed to the ballad of "The Eve of St. John," he says that he wrote that ballad in celebration of Smailholm tower and its vicinity and in the epistle preliminary to the third canto of Marmion, he notices the influence which the place had exerted on his tastes. In 1406, Robert Pringle of Smailholm, which became his designation after the erection of the tower, had a safe-conduct from Henry IV., to go to England, and in 1419 he had another, from Henry V., with John Wallace, to pay the ransom of James de Douglas, who succeeded his grand-nephew as seventh earl of Douglas, November 24, 1440, and was called James the Gross. The laird of Smailholm accompanied Archibald, fourth earl of Douglas, duke of Touraine, (the Douglas of Shakespeare,) on his famous expedition to France, in 1423, and was slain, with him, at the battle of Verneuil, the following year. (See vol. ii. p.43.)”
The Douglas Archive. http://www.douglashistory.co.uk/history/Septs/pringle_of_whitsome.htm