Smolensk, a strong and strategically important fortress, was a part of the Grand Duchy of Lithuania since 1404.

Ivan III of Russia launched the second Muscovite–Lithuanian War in 1500 and Lithuanians suffered a great defeat in the Battle of Vedrosha.

[2] The Russian army plundered Orsha and Vitebsk and attacked Smolensk with artillery.

[2] The indecisive but bloody Battle of Lake Smolino in September[3] as well as Lithuanian reinforcements brought by Great Hetman (commander of the army) Stanislovas Kęsgaila,[4] forced the Russians to retreat.

[5] The Grand Duchy of Lithuania lost approximately 210,000 square kilometres (81,000 sq mi),[6] or a third of its territory: Chernihiv, Novhorod-Siverskyi, Starodub, and lands around the upper Oka River.