The encirclement began as the Demyansk Offensive Operation, the first phase being carried out from 7 January until 20 May 1942 on the initiative of General Lieutenant Pavel Kurochkin, commander of Northwestern Front.

However, owing to the very difficult wooded and swampy terrain, and heavy snow cover, the initial advance by the Front was very modest against stubborn opposition.

From the middle of February, the weather improved significantly, and while there was still considerable snow on the ground at this time, resupply operations were generally very successful due to inactivity of the Soviet Air Forces (VVS) in the area.

Over the winter and spring, the Northwestern Front launched a number of attacks on the "Ramushevo corridor" that formed the tenuous link between Demyansk and Staraya Russa but was unable to reduce the pocket.

The success of the Luftwaffe convinced Reichsmarschall Hermann Göring and Hitler that they could conduct effective airlift operations on the Eastern front.

[13] After the German 6th Army was encircled in the Battle of Stalingrad, Göring convinced Hitler to resupply the besieged forces by airlift until a relief effort could reach them.

[14] However the sheer scale of the effort required in Stalingrad – calculated at 750 tons per day – greatly exceeded the Luftwaffe's now-depleted capacities,[15] when up against the now-strengthened Soviet Air Forces.

The Stalingrad airlift effort ultimately failed to deliver sufficient supplies before the airfields were overrun by the Soviets, and the Germans estimated that they lost 488 transports, as well as 1,000 personnel.