Although the western Anglo-Scottish Border was agreed in Edward II's reign with David II of Scotland in 1330, to run along the course of the Esk and Liddle from Gretna to Kershopefoot to delineate between the English and Scottish West Marches, in practice this region was controlled by Wardens who usually held the land in their own right. In Scotland the Maxwells, Johnstones and Scotts securely held the Scottish West March to Gretna and Langholm and in England the region was controlled by the Warden from Carlisle. The Esk basin at Arthuret was a marshy bogland called Sollomoss which was difficult to police and with the Scottish jurisdiction having difficulty policing their side from Gretna to Canonbie.

The Debateable Land arose because the Graemes, Armstrongs, Elliots and Bells were too powerful and the Wardens left them alone. These four families raided equally in both England and Scotland, claiming alliegance to neither country; it actually suited both Governments to have such a "buffer" zone, so the district became a sort of no-mans land, where neither country could or would enforce their jurisdiction. Eventually the lawlessness of all such no-go area's prevailed and both Wardens demanded that the Debateable Land be eradicated. So in 1552 a commission under the French ambassador was appointed to finalise the Border line. Typically he simply divided the Debateable land into two halves cut by a man-made ditch called the Scots Dyke, giving the western half to England and the eastern half to Scotland.....intriguing that England received the main western road into Scotland, while Scotland received little else but moorland. In point of fact nothing much changed, except that a Dyke was constructed, but the four families were unimpressed and continued their raiding activities just as equitably and lawlessly as they had in the past.

An amusing anecdote about how the debateable land came to belong to neither side is told around the local hostelries when the natives are in their "cups". Apparently at some time around the early 16th century, the English West March Warden and the Scottish West March Warden grew tired of being unable to enforce their jurisdictions, because no-one knew exactly where the border lay. They then met and agreed that two Scottish nobles from Edinburgh along with two English nobles from London would mark out an agreed border line. These four just worthies met up at Annie-Janes pub the evening before the day appointed for this purpose and as nobles do consumed vast quantities of the local brew as a pre-requisite for their hard task. In the morning, the Englishmen were up early and being impatient to be about their task, left without the two Scotsmen, to mark out the border from Kershopefoot to Gretna.

Meanwhile the two Scotsmen arriving at breakfast late, asked about the route the Englishmen have taken, to be told by the locals to follow the River Liddle to the Esk and then to Langtoon, which they would recognise by it’s bridge across the Esk. Setting off the two Scotsmen travel down the Liddle to the Esk and meeting a shepherd ask him the way to the Lang place with the bridge. They are duly directed up the Esk to Langholm. So the nett result is two borders: one from Kershope to Longtown to Gretna; and the other from Kershope to Langholm to Gretna. The resulting 12 mile long by 5 mile wide strip between the two became the Debateable Land.