[1] Alexander of Lithuania unsuccessfully tried to even make the Crimean Khanate under Meñli I Giray and Moldavia under Stephen III begin hostilities against Muscovy, with which they were allied.

[6] The Muscovites agitated the Grand Duchy's Eastern Orthodox inhabitants against their Catholic rulers and tried to enflame to renounce Lithuania and join Muscovy.

[2][6] The marriage of Alexander and Elena, daughter of Ivan III, in 1495 did not lead to peaceful Lithuanian-Muscovite relations or a common policy against the Tatars, as was hoped for by some.

[2] The main object contested between Muscovy and Lithuania were the vast territories close to the Dnieper, which was strategically important for communication and trade.

[2] Confident in his strength and underestimating the enemy, the Grand Hetman of Lithuania Konstanty Ostrogski decided to attack first with the 4,000 Lithuanian soldiers.

[2] The Lithuanians attacked the camp of the central Muscovites forces at a tributary of the Dnieper, the Vedrosha River, but were tricked into a well-organized ambush.

[2] Meanwhile, the other part of the Lithuanian army, led by Alexander of Lithuania, was in Borisovsky district, about 200 kilometres (120 mi) from Smolensk, too far away to quickly salvage the situation.