Ukrainian anarchist guerrilla bands were active during the Russian Civil War. Some claimed to be loyal to the Ukrainian state, but others acknowledged no allegiance; all fought both Red and White Russians with equal ferocity in the opening stages of the Civil War. Of all the anarchist groups, the most famous and successful was that of the peasant anarchist leader Nestor Makhno, aka Batko ("Father"), who began operations in the southeastern Ukraine against the Hetmanate regime in July 1918. In September, he formed the Revolutionary Insurrectionary Army of Ukraine, or Anarchist Black Army, with arms and equipment largely obtained from retreating Austro-Hungarian and German forces. During the Civil War, the Black Army numbered between 15,000 and 110,000 men and was organized on conventional lines, with infantry, cavalry, and artillery units; artillery batteries were attached to each infantry brigade. Makhno's cavalry incorporated both regular and irregular (guerrilla) horse-mounted forces, and was considered among the best-trained and most capable of any of the cavalry units deployed by any side in the Russian Civil War.
The Bolshevik government and Red Army commanders often referred to the Black Army as "Makhnovist forces", because they pointedly declined to accord the Ukrainian anarchists the status of having an army or a legitimate political movement. Volin described the Insurrectionary Black Army of the time (less its cavalry, which normally ranged far afield) as follows: The infantry, when it was not fighting, led the march of the army ... tachankas. Each of these vehicles, which were drawn by two horses, carried the driver on the front seat and two soldiers behind them. In some sections a machine-gun was installed on the seat between them. The artillery brought up the rear. A huge black flag floated over the first carriage. The slogans Liberty or Death and The Land to the Peasants, the Factories to the Workers were embroidered in silver on its two sides.
A main obstacle to the anarchist army, and one which it never overcame throughout its existence, was a lack of access to primary industrial manufacturing resources, specifically factories capable of producing large amounts of arms and ammunition. Denied large-scale arms shipments from the Bolshevik government in Moscow, and without arsenal manufacturing centers of its own, the Black Army was forced to rely on captures of munition depots and supplies from enemy forces, and to procure food and horses from the local civilian population.
By early 1919, the Bolshevik government had withdrawn most Red Army forces from Ukraine after White successes in the south. The remaining Red Army troops who had stayed in various parts of Ukraine were suspicious of their commanders, and angry at the withdrawals from Ukraine, which they considered a defection from the revolutionary cause. At the end of July, 1919, Red Army detachments numbering some 40,000 troops in Crimea mutinied and deposed their commanders; many set out to join Makhno's anarchist Black Army. The mutiny was organized by some of Makhno's anarchist comrades who had remained commanders in the ranks of the Red Army, including Kalashnikov, Dermendzhi, and Budanov; these men also planned the transfer of forces. Large numbers of Red Army soldiers advanced from Novi Bug to Pomoshchnaya in search of Makhno's Black Army, bringing with them, as captives, their former commanders: Kochergin, Dybets and others. The mutineers joined Black Army forces at Dobrovelychkivka in the municipality of Kherson at the beginning of August 1919. For the Bolshevik government in Moscow, this defection was a major blow; since almost nothing remained of the Red Army in southern Ukraine and the Crimea, Bolshevik influence in the area vanished.
Makhno and the Ukrainian anarchist Black Army, at first declared 'bandits' and 'outlaws' by the Moscow's Bolshevik government, were welcomed after General Anton Denikin threatened to overrun Moscow in a drive towards the city in 1919. After concluding an agreement with the Ukrainian Directory, Makhno and his subordinate commanders made plans to turn the Black Army east and attack Denikin's Volunteer Army and its lines of supply, hoping to break through his lines.