The division began forming in accordance with a directive of the Northwestern Front dated 8 November 1941 in the area of Kuzhenkino and Yedrovo.

[4] On 19 January, simultaneously with the successful advance of the 33rd Rifle Division, the vanguard of the 257th reached the area of Losevo, implying a move on Velikiye Luki.

[8] Continuing the advance on Velikiye Luki, the flank guards of the division engaged scouts from Gruppe Meyer during the afternoon of 27 January.

[9] The skiers of the division and partisan detachments operated against Gruppe Meyer, defending the gap between Kholm and Velikiye Luki.

From late January to November, the division as part of the 3rd Shock Army of the Kalinin Front defended positions northeast of Velikiye Luki.

[11] On 15 June, the 31st Rifle Brigade and two ski battalions were placed under the control of the division, expanding its defensive line from 40 to 80 km.

During its months on the defensive, the division conducted reconnaissance raids against the opposing German positions with the goal of capturing prisoners and destroying infrastructure.

[14] In this period of relative quiet on the front, between 1 June and 20 September, the 257th lost 320 men: 100 killed, 188 wounded, two captured and 30 missing.

The attacks of the 2nd Guards Rifle Corps failed and after several attempts on Skaruyevo the regiment retreated into the forest 700 meters to the southwest of the village.

[19] As the German attack ground towards the relief of the Kholm Pocket, the 953rd was replaced by the 164th Rifle Regiment of the 33rd Division by the end of 5 May.

[13] During the winter of 1942–1943, the 257th fought in the Battle of Velikiye Luki to destroy the German garrison of the city, which was captured on 17 January 1943.

For the battle in the city, the division trained extensively for urban warfare, practicing attacks upon mock German fortifications built from snow.

Dyakonov created five assault detachments of up to a hundred soldiers from the personnel of the division, consisting of sappers, machine gunners, mortarmen, smoke screen deployers, artillerymen, and Ampulomet throwers.

Due to lack of preparation, the 357th and the 7th Estonian Rifle Divisions, who attacked with reinforced battalions instead of assault groups, failed to achieve their objectives and the city was not captured by the target date of 16 December.

[21] As a result, army commander Kuzma Galitsky decided to send the 249th Estonian Rifle Division into action to break the stalemate, while the 257th was ordered to capture strongpoints on the outskirts of the city that flanked the advancing forces.