It was all quite illegal.

From The Road to Guilford Courthouse by John Buchanan. Page 206.

The Over Mountain People were largely Scotch Irish, but the mixing had already begun, for among them were sizeable numbers of English and some Germans and Welsh. At the time of which we write they lived in the extreme northeastern corner of what is now Tennessee, along the Watauga, Nolachucky, and Holston Rivers, where Tennessee, Virginia, and North Carolina meet. They were squatters on Cherokee land, for it was the official policy of the British government to keep white settlers east of the mountains, and to that end the Proclamation Line of 1763 was established. The line followed the watershed of the Appalachian Mountains. The country west of the line was Indian territory under the charge of the commander in chief of the British Army in America. That did not prevent sixteen families from North Carolina, led by James Robertson and his deputy John Sevier, from crossing the mountains and stopping their wagons on the banks of the Watauga River, at a beautiful spot called Sycamore Shoals (modern Elizabethton, Tennessee). There they established the Watauga settlements and leased two large tracts of land from the Cherokee.

It was all quite illegal. The Royal Governor of Virginia, Lord Dunmore, called it a “dangerous example,”26 and from the British point of view, and the Cherokee, he was right. But who was going to do anything about it? Three years later the Watauga Association purchased their leased lands from the Indians, but other Cherokee, including young Dragging Canoe, vehemently objected. The subject of Indian land tenure, wellspring of historical and modern controversies, is not our concern. All we need know is that Dragging Canoe and several hundred warriors were back in July 1776, this time in war paint. But the besieged settlements, outnumbered and on their own, held; and from one fort Over Mountain riflemen sallied and in a hard fight on the South Fork of the Holston defeated the Cherokee.

The Indian threat would not end for several years. The bitter struggle in the Appalachians was a phase in a war that began in the early 1600s and lasted for almost three centuries: undeclared, unrelenting, unforgiving. The Over Mountain Man, hardened by the toil of pioneering, was further hardened by Indian fighting. His life could indeed be short, nasty, and brutal. But if he survived falling trees, fever, snake bites, drowning, disease, backbreaking labor, blood poisoning, and the scalping knife, he rode into a fight a warrior for the ages.