[6] The principality contained a number of other important cities that usually possessed subordinate status, notable among them Bryansk, Vyazma and Mozhaysk.

In 1355, Algirdas, Grand Duke of Lithuania, attacked Smolensk and captured Rzhev, Bely, Mstsislaw, Toropets.

Smolensk later fought alongside Moscow against Mikhail II of Tver in 1372–1374 and against the Golden Horde in the Battle of Kulikovo (1380).

[9] In 1386, Prince Sviatoslav IV of Smolensk [ru] was killed in the Battle of the Vikhra River against the Lithuanians when he supported Andrei of Polotsk and his rebellion against his younger half-brother Jogaila.

However, Skirgaila, the leader of the Lithuanian forces in battle, wedded to Sviatoslav's niece, and granting permission to Yury of Smolensk was in command, to succeed his father.

In the 17th century, the Rus' under Russian control attempted to bring the city into their expanding state again, and despite defeat in the "Smolensk War" (1632–1634) the Tsardom of Russia captured the city in 1654 at a time when the revolt of the Dnieper Cossacks in the Khmelnytsky Uprising (1648–1657) partially distracted the Commonwealth.

The famous trade route from the Varangians to the Greeks passed through the principality and was an important source of income for its rulers.