Principality of Smolensk
Roslavl was founded as Rostislavl in the 1130s or 1140s. The name is likely due to Prince Rostislav of Smolensk, who was the founder of the fortress. It belonged to the Principality of Smolensk. The area belonged intermittently to the Principality of Smolensk and the Grand Duchy of Lithuania. In 1376, Roslavl was transferred to Lithuania and became the center of a principality. It was chartered under Lithuanian rule in 1408. In 1515, it was conquered by the Grand Duchy of Moscow, but in 1618 transferred to Poland. Under Polish-Lithuanian rule Roslavl was part of the Smolensk Voivodeship. In 1667, according to the Truce of Andrusovo, Roslavl was transferred back to Russia. During all this period, it was a fortress at the border, and the fortifications were extensively used. The last time they were in use in 1706, during the Great Northern War. In the course of the administrative reform carried out in 1708 by Peter the Great, the area was included into Smolensk Governorate and remained there until 1929, with the exception of the brief periods between 1713 and 1726, when it belonged to Riga Governorate, and between 1775 and 1796, when Smolensk Governorate was transformed into Smolensk Viceroyalty. It was the center of Roslavlsky Uyezd.