The 'Battle of the Kholm Pocket' was fought between Soviet and German troops for Kholm, in the area to the south of Leningrad, on the Eastern Front (23 January/5 May 1942).

A much larger pocket was meanwhile surrounded in Demyansk, about 60 miles (100 km) to the north-east of Kholm, both pockets having come into existence in the aftermath of the German retreat following the defeat in the 'Battle of Moscow'. The air supply of the German forces trapped in Kholm and Demyansk was successful, but for the Germans had unfortunate consequences as it led to an exaggerated confidence of the Luftwaffe’s ability to supply encircled forces by air, and this had disastrous consequences in the 'Battle of Stalingrad' late in 1942 and early in 1943.

In the Kholm pocket, 5,500 German troops held out for 105 days. The pocket was supplied by air, but as it was too small to accommodate an airstrip large enough for operations by transport aircraft, supplies had to be dropped for location and recovery by the German defenders even as the pocket was steadily squeezed by the Soviet forces, largely on its eastern side. Most of the German units in the pocket, whose defenders were commanded by Generalleutnant Theodor Scherer, were provided by parts of Generalleutnant Horst Freiherr von Uckermann’s (from 20 March Generalleutnant Viktor Langpart’s) 218^th Division, the 65^th Reserve-Polizeibataillon, the 553^rd Infanterieregiment of Generalleutnant Helmuth Castorf’s (from 7 March Generalmajor Bruno Hippler’s and from 22 March Generalleutnant Dr Johannes Mayer’s) 329^th Division, parts of Generalleutnant Erwin Rauch’s 123^rd Division, the 8^th Jagdkommando and the 3/1^st Luftwaffenfeldregiment.

The attacking Soviet forces, under the command of General Leytenant Nikolai F. Vatutin, the chief-of-staff of General Leytenant Pavel A. Kurochkin’s North-West Front, were centred on the 33^rd and 391^st Divisions of General Leytenant Maksim A. Purkayev’s 3^rd Shock Army, supported by 20 tanks.

Kholm was finally reoccupied by the Soviet forces on 21 February 1944.