The '1^st Battle of Kiev' was the German encirclement within 'Barbarossa' of Soviet troops in the vicinity of Kiev and the capture of that city, the largest in Ukraine (7 July/26 September 1941).

This encirclement is considered the largest encirclement in the history of warfare by the number of troops trapped. Much of General Polkovnik Mikhail P. Kirponos’s South-Western Front was encircled, but small groups of Soviet troops managed to escape from the pocket in the days after the German armoured pincers met in the area to the east of the city, these escapees including the headquarters of Marshal Sovetskogo Soyuza Semyon M. Budyonny’s South-Western Theatre, Marshal Sovetskogo Soyuza Semyon K. Timoshenko’s Western Front and Commissar Nikita S. Khrushchev of the South-Western Theatre’s military council. Kirponos was trapped behind German lines and was killed while trying to break out.

The battle was an unprecedented Soviet defeat, exceeding even the 'Battle of Białystok-Minsk' in June and July 1941. The encirclement trapped 452,700 soldiers, 2,642 guns and mortars and 64 tanks, of which scarcely 15,000 men had escaped from the encirclement by 2 October. The South-Western Front suffered 700,544 casualties, including 616,304 men killed, captured or missing during the battle. The 5^th, 37^th, 26^th, 21^st, and 38^th Armies, comprising 43 divisions, were almost totally annihilated and the 40^th Army suffered very severe losses. Like the Western Front before it, the South-Western Front had therefore to be wholly re-created.

After the rapid progress of Generalfeldmarschall Fedor von Bock’s Heeresguppe 'Mitte' through the central sector of the Eastern Front, a huge salient had started to develop around its junction with Generalfeldmarschall Gerd von Rundstedt’s Heeresgruppe 'Süd' by a time early in July 1941. On 7/8 July, the German forces broke through the defences of the 'Stalin Line' in the south-eastern portion of the Zhitomir region, which ran along the 1939 Soviet border. By 11 July 1941, the Axis ground forces had reached the Dniepr river’s Irpin river tributary 9.3 to 12.4 miles (15 to 20 km) to the west of Kiev. The initial German attempt to enter the city was thwarted by troops of the Kiev fortified district, and the counter-offensive of the Soviet 5^th and 6^th Armies. The advance on Kiev was halted and the main German effort was then shifted toward the Korosten region to the north-west of Kiev, where the Soviet 5^th Army was concentrated. At the same time, Generalfeldmarschall Ewald von Kleist’s 1^st Panzergruppe was forced to switch to defensive as a result of the Soviet 26^th Army’s counter-offensive. A substantial Soviet force, nearly the entire South-Western Front, was positioned in the salient both in and around Kiev. By the end of July, the Soviet front had lost some of its formations and units as a result of the critical situation of the Southern Front (the 6^th and 12^th Armies) caused by the advance of General Karl-Heinrich von Stülpnagel’s 17^th Army.

While lacking mobility and armour, as a result of their great tank losses in the 'Battle of Uman', on 3 August the surviving Soviet forces nonetheless posed a significant threat to the German advance and represented the largest single concentration of Soviet troops on the Eastern Front at that time. Both the Soviet 6^th and 12^th Armies were encircled at Uman, where some 102,000 Soviet troops were taken prisoner. On 30 July, the German forces resumed their advance onto Kiev, with Generalfeldmarschall Walter von Reichenau’s 6^th Army attacking positions between the Soviet 26^th Army and the formations of the Kiev defensive region.

On 7 August, the German advance was halted again by the Soviet 5^th, 37^th and 26^th Armies, supported by the Pinsk Naval Flotilla. With the help of the local population around the city of Kiev, anti-tank ditches were dug and other obstacles erected, the latter including of 750 pillboxes and 100,000 mines planted along the 28 miles (45 km) front. Some 35,000 soldiers were mobilised from local population along with some partisan detachments and two armoured trains.

On 19 July, Adolf Hitler had issued his Führerweisung Nr 33, which cancelled the assault on Moscow in favour of a drive to the south to complete the encirclement of Soviet forces surrounded in the Kiev region. On 12 August, Hitler issued a supplement to the Führerweisung Nr 34, which was a compromise between Hitler, who was convinced the correct strategy was to clear the salient occupied by Soviet forces on right flank of Heeresgruppe 'Mitte', in the vicinity of Kiev, before resuming the drive to Moscow, and a number of senior staff and operational commanders, who advocated an advance on Moscow as soon as possible. The compromise required Generaloberst Heinz Guderian’s 2^nd Panzergruppe and Generaloberst Hermann Hoth’s 3^rd Panzergruppe of Heeresgruppe 'Mitte', which were redeploying in order to aid Generalfeldmarschall Wilhelm Ritter von Leeb’s Heeresgruppe 'Nord' and von Rundstedt’s Heeresgruppe 'Süd' respectively, to be returned to Heeresgruppe 'Mitte', together with Generaloberst Erich Hoepner’s 4^th Panzergruppe of Heeresgruppe 'Nord', once their objectives had been achieved. The three Panzergruppen, under the control of Heeresgruppe 'Mitte', would then spearhead the advance on Moscow. Initially, Generaloberst Franz Halder, the chief-of-staff of the Oberkommando des Heeres, and von Bock, commander of Heeresgruppe 'Mitte', were satisfied by the compromise, but their optimism quickly faded as the plan’s operational realities proved to be too challenging.

On 18 August, the Oberkommando des Heeres submitted a strategic survey to Hitler with regard to the continuation of operations on the Eastern Front. The survey made the case for the drive on Moscow, arguing once again that Heeresgruppe 'Nord' and Heeresgruppe 'Süd' were strong enough to accomplish their objectives without assistance from Heeresgruppe 'Mitte'. The survey also pointed out that there was sufficient time before the onset of winter to conduct only a single decisive operation against Moscow.

On 20 August, Hitler rejected the proposal based on the idea that the most important objective was to deprive the USSR of its industrial areas. On 21 August, General Alfred Jodl, the chief of the operations staff of the Oberkommando der Wehrmacht, issued a directive, which summarised Hitler’s instructions, to Generalfeldmarschall Walther von Brauchitsch, commander-in-chief of the army. The directive reiterated that the capture of Moscow, before the onset of winter, was not a primary objective. Rather, it emphasised that the most important task to be achieved before the onset of winter were the seizure of Crimea and the industrial and coal region of the Don river; the isolation of the oil-producing regions of the Caucasus from the rest of the USSR; and, in the north, the encirclement of Leningrad and the establishment of a land link with the Finns. Among other instructions, it also instructed that Heeresgruppe 'Mitte' was to allocate sufficient forces to ensure the destruction of the 'Russian 5^th Army' (the Soviet forces in the salient according to Hitler) and, at the same time, to prepare to repel Soviet counterattacks in the central sector of its front. Halder was dismayed, and later described Hitler’s plan as 'utopian and unacceptable', concluding that the orders were contradictory, that Hitler alone must bear the responsibility for inconsistency of his orders, and that the Oberkommando des Heeres could no longer assume responsibility for what was occurring. However, Hitler’s instructions still accurately reflected the original intent of the 'Barbarossa' directive, of which the Oberkommando des Heeres had been fully aware from the start. The adjutant of von Brauchitsch, Gerhard Engel, in his diary for 21 August summarised it as 'a black day for the army'. Halder offered his own resignation and advised von Brauchitsch to do the same, but the latter declined to do so, stating Hitler would not accept the gesture, and nothing would change anyhow. Halder withdrew his offer of resignation.

On 23 August, Halder met von Bock and Guderian in the Belorussian town of Borisov, and afterward flew with Guderian to Hitler’s headquarters in East Prussia. During a meeting between Guderian and Hitler, with neither Halder nor von Brauchitsch present, Hitler allowed Guderian to make the case for advancing on to Moscow, and then rejected his argument. Hitler claimed his decision to secure the northern and southern sectors of western USSR were 'tasks which stripped the Moscow problem of much of its significance' and was 'not a new proposition, but a fact I have clearly and unequivocally stated since the beginning of the operation'. Hitler also argued that the situation was even more critical because the opportunity to encircle the Soviet forces in the salient was 'an unexpected opportunity, and a reprieve from past failures to trap the Soviet armies in the south'. The German leader also declared that 'the objections that time will be lost and the offensive on Moscow might be undertaken too late, or that the armoured units might no longer be technically able to fulfil their mission, are not valid'. Hitler reiterated that once the flanks of Heeresgruppe 'Mitte' had been cleared, especially the salient in the south, then he would allow the army group to resume its drive on Moscow, an offensive, he concluded, which 'must not fail'. Guderian returned to the 2^nd Panzergruppe and began the southern thrust in an effort to encircle the Soviet forces in the salient.

The bulk of the 2^nd Panzergruppe and Generalfeldmarschall Maximilian Reichsfreiherr von Weichs’s 2^nd Army were detached from Heeresgruppe 'Mitte' and sent south, their mission being to encircle Budyonny’s South-Western Front in conjunction with von Kleist’s 1^st Panzergruppe of Heeresgruppe 'Süd', which was advancing from a south-easterly direction.

After the crossing of the Dniepr river by German forces on 22 August, the city of Kiev came under threat of direct encirclement, and the command of the South-Western Front appealed to the Stavka for authorisation to withdraw its forces from Kiev. On 17 September, the Soviet chief-of-staff, Marshal Sovetskogo Soyuza Boris M. Shaposhnikov, wrote to the South-Western Front authorising withdrawal from Kiev, when the encirclement had already been completed when German forces met at Lokhvitsa, in the Poltava region.

The Panzergruppen made rapid progress. On 12 September, von Kleist’s 1^st Panzergruppe, which had by now turned to the north and crossed the Dniepr river, emerged from its bridgeheads at Cherkassy and Kremenchuk. Continuing north, it cut across the rear of Budyonny’s South-Western Front. On 16 September, it made contact with Guderian’s 2^nd Panzergruppe, advancing to the south, at Lokhvitsa, 120 miles (190 km) to the east of Kiev. Budyonny was now trapped, soon relieved by an order of Iosif Stalin on 13 September, and replaced by Timoshenko, in command of the South-Western Direction.

After this, the fate of the encircled Soviet armies was sealed. With no mobile forces or supreme commander left, there was no possibility of a break-out. The infantry of Heeresgruppe 'Süd''s 17^th Army and 6^th Army soon arrived, along with the 2^nd Army, also on loan from Heeresgruppe 'Mitte', and marching behind Guderian’s tanks. The infantry formations embarked systematically on the reduction of the pocket with the assistance of the two Panzergruppen. The Soviet armies encircled at Kiev did not yield easily and a savage battle, in which the Soviets were bombarded by artillery, tanks and aircraft, had to be fought before the pocket was finally overwhelmed.

By 19 September, Kiev itself had fallen, but the encirclement battle continued. After 10 days of heavy fighting, the last remnants of troops to the east of Kiev surrendered on 26 September. Several Soviet armies, namely the 5^th, 37^th and 26^th Armies, were now encircled, as were separate detachments of the 38^th and 21^st Armies. The Germans claimed to have captured as many as 665,000 Soviet soldiers, although these claims are known to have included a large number of civilians suspected of evading capture.

During withdrawal from Kiev, on 20/22 September 1941 at Shumeikove Hai near Dryukivshchyna, several members of the Soviet headquarters staff were killed, including Kirponos (commander), Mykhailo Burmystenko (a member of military council), and General Major Vasili I. Tupikov (chief-of-staff). Some 15,000 Soviet troops managed to break out of the encirclement.

As a result of Guderian’s wheel to the south, the Germans had been able to destroy the entire South-Western Front east of Kiev during September. The Germans inflicted nearly 700,544 casualties on the Soviets, but at the same time the Soviet forces to the west of Moscow delivered many attacks on Heeresgruppe 'Mitte'. Although most of these attacks failed, the Soviet attacks in the 'Yelnya Offensive Operation' succeeded in forcing the German forces to abandon the town, and resulted in the first major German defeat in 'Barbarossa'. With its southern flank secured, Heeresgruppe 'Mitte' launched 'Taifun' (i) in the direction of Vyaz’ma during October.

Over the objections of von Rundstedt, Heeresgruppe 'Süd' was ordered to resume the offensive and overran nearly all of the Crimea and left-bank Ukraine before reaching the edges of the Donbas industrial region. However, after four months of continuous operations, von Rundstedt’s forces were at the brink of exhaustion, and suffered a major defeat in the 'Battle of Rostov-na-Donu'. The infantry formations of Heeresgruppe 'Süd' fared little better and failed to capture the vital city of Kharkov before almost all its factories, equipment and skilled workers had been evacuated to fresh locations lying to the east of the Ural mountains.

Despite the order for the wholesale destruction of Kiev issued in the supplement to Führerweisung Nr 34 from 12 August, the city was spared, to Hitler’s fury, as there had been no fighting in it. The German troops, who occupied Kiev on 19 September, were surprised by the detonations of a series of Soviet radio-controlled mines in the city centre from 24 September onward, the first of which also killed a number of local civilians reporting at the German field command to surrender banned items. The resulting fire, which was not put out until 29 September, offered the German authorities a pretext to start the mass murder of Jews in Babi Yar on the same day. As the city had not been razed, the German leadership launched the plan to starve it while officially attributing the food shortages to the consequences of Soviet economic policies. Ultimately the implementation of the German 'hunger plan' in occupied Kiev was restrained by the fears of an uprising behind the lines, and instead the city was forcibly evacuated and subjected to widespread looting and burning during the German withdrawal in September/November 1943.

Immediately after World War II’s end, prominent German commanders argued that had operations at Kiev been delayed, and had 'Taifun' (i) been launched in September rather than in October, the German army would have reached and captured Moscow before the onset of winter. However, a prominent historian of the war on the Eastern Front has argued that had 'Taifun' (i) been launched in September, it would have met greater resistance as a result of the fact that the Soviet forces would not have been weakened by their offensives to the east of Smolensk. The offensive would have also been launched with an extended right flank. The historian also claims that regardless of the final position of German troops when winter came, they would have still faced a counter-offensive by the 10 reserve armies raised by the Soviets toward the end of the year, who would also be better equipped by the vast industrial resources in the area of Kiev, and therefore that had Kiev not been taken before the 'Battle of Moscow', the entire operation would have ended disastrously for the Germans.