The 'Roslav-Novozybkov Offensive Operation' was a Soviet offensive by the forces of the Bryansk Front against the the German 2^nd Panzergruppe and 2^nd Army in the Bryansk and Sumy areas as part of the 'Smolensk Strategic Defensive and Offensive Operation' (30 August/12 September 1941).

The undertaking was the last of nine sub-operations within what the Soviets designated the 'Smolensk Strategic Defensive and Offensive Operation'. The other eight elements of this undertaking were the 'Polotsk Defensive Operation' (2 July/16 July), the 'Smolensk Defensive Operation' (10 July/10 August), the 'Smolensk Offensive Operation' (21 July/7 August), the 'Rogachev-Zhlobin Offensive Operation' (13/24 July), the 'Gomel-Trubchevsk Defensive Operation' (24 July/30 August), the 'Dukhovshchina Offensive Operation' (17 August/8 September) and the 'Yelnya Offensive Operation' (30 August/8 September).

This offensive constituted an attempt by General Leytenant Andrei I. Eremenko’s Bryansk Front to destroy Generaloberst Heinz Guderian’s 2^nd Panzergruppe of Generalfeldmarschall Fedor von Bock’s Heeresgruppe 'Mitt' after it turned south toward Kiev. The offensive failed as a result of the over-dispersal of the Soviet armoured forces and poor intelligence, as a result of which the 2^nd Panzergruppe inflicted heavy casualties on the Bryansk Front’s forces, significantly weakening it in advance of 'Taifun' (i), which was launched against Moscow three weeks later. The German troops continued their advance to the south, resulting in the encirclement battle for Kiev, the main city of Ukraine.

On 28 August, the 2^nd Panzergruppe, diverted from its north-eastward progress in the direction of Mogilev, continued to advance to the south, crossing the Desna river near Novgorod-Seversky and Korop by the end of the day. The Stavka ordered a concentration of the warplanes of the air forces attached to the Bryansk Front and General Polkovnik Mikhail P. Kirponos’s South-West Front in order that powerful blows designed to blocking the advance of the 2^nd Panzergruppe, but the Soviet aircraft failed to halt the German progress. By the end of 29 August, the leading Kampfgruppe of Generalleutnant Wolfgang Fischer 's 10^th Division (mot.) within General Leo Freiherr Geyr von Schweppenburg’s XXIV Corps (mot.) had driven forward some 12.5 miles (20 km) to the south, reaching positions to the north of the Seym river, itself 12.5 miles (20 km) to the north of Bakhmach, and in the process meeting and engaging elements of the 293^rd Division of General Major Kuzma P. Podlas’s 40^th Army near Korop and the LXVII Corps of General Leytenant Vasili Cherevichenko’s 21^st Army’s along the Seym river. Podlas’s 40^th Army, which became part of the South-West Front on 26 August, was responsible for defending the front’s right flank and maintaining contact with the Bryansk Front on its right. The army included the 135^th Division, 293^rd Division, 10^th Tank Division, II Airborne Corps and 5^th Anti-Tank Brigade.

At this stage of the 'Barbarossa' campaign, it should be noted, the XXIV Corps (mot.) averaged a daily operational strength of about 320 tanks (including 128 PzKpfw III medium and PzKpfw IV battle tanks, and 192 a miscellany of PzKpfw I and PzKpfw II obsolete light tanks, and command tanks) which was well below half of its strength at the beginning of 'Barbarossa'. At the same time, Generalleutnant Walter Model’s 3^rd Panzerdivision reached western approaches to Glukhov, some 30 miles (50 km) to the south-east of the Desna river at Novgorod-Seversky, where it met 40^th Army’s main body, including the 10^th Tank Division and the 5^th Anti-Tank Brigade.

Behind the 10^th Division (mot.) and 3^rd Panzerdivision, Generalmajor Willibald Freiherr von Langermann und Erlencamp’s 4^th Panzerdivision of the XXIV Corps (mot.), and Generalleutnant Wilhelm Ritter von Thoma’s 17^th Panzerdivision and Generalmajor Walter von Boltenstern’s 29^th Division (mot.) of General Joachim Lemelsen’s XLVII Corps (mot.) were echeloned to the rear at Novgorod-Seversky and to the west of Trubchevsk. The 4^th Panzerdivision was engaged with the 52^nd Cavalry Division of General Major Konstantin D. Golubev’s 13^th Army near Novgorod-Seversky and the same army’s main forces to the west of Trubchevsk. Farther to the rear, Generalleutnant Walther Nehring’s 18^th Panzerdivision of the XLVII Corps (mot.) was quickly moving to the south from Roslavl while mopping up stragglers of the 13^th Army in the 2^nd Panzergruppe's rear in the area to the west of the Desna river.

To the west of the 2^nd Panzergruppe, infantry divisions of Generalfeldmarschall Maximilian von Weichs’s 2^nd Army pushed the remnants of Kuznetsov’s 21^st Army and Golubev’s 3^rd Army, both of the Bryansk Front, in the direction of Chernigov while eliminating the elements of the 21^st Army surrounded in a large pocketed salient to the north-east of Chernigov and to the north of the Desna river.