The advent of the October Revolution caused the outbreak of civil war in Ukraine, as the forces of the Central Council and the Soviets struggled to take power in the country.

[25] Under pressure by the advancing Makhnovists, on 30 December, Slaschov's White forces finally quit Katerynoslav province and retreated to Crimea,[26] where they built a new base of operations.

[28] The Makhnovists had underestimated the rapid advance of the Red Army, with Peter Arshinov later analyzing that a tactical error had been made by the insurgents in not establishing a front from Oryol to Poltava.

[39] Beset by epidemic typhus and more inclined to fight on their home turf than in western Ukraine,[40] the Insurgent Army responded with a categorical rejection of the order,[41] just as the Bolshevik command had anticipated.

[48] By 15 January, the Red Army had occupied Nikopol,[49] where 15,000 insurgents were sick with typhus, shooting the Makhnovist commanders stationed there[50] and capturing large amounts of war material.

[54] With the insurgent army taken care of, the Bolsheviks turned their attention towards carrying out the Red Terror in Ukraine, with Leon Trotsky himself ordering that all supporters of the partisans be "mercilessly punish[ed]".

[59] The Bolshevik government implemented war communism in Ukraine, introducing a strict system of rationing and food requisitioning,[60] which confiscated agricultural produce and livestock from the peasantry, and even forbade them from fishing, hunting or collecting lumber.

[69] The insurgents began to prosecute a campaign of guerrilla warfare against the Red Army throughout left-bank Ukraine, where the Makhnovists knew the land and could carry out a series of surprise attacks against the Bolshevik forces.

Towards the end of February, the Estonian Red Riflemen in Huliaipole were eliminated in a surprise attack,[70] after which its commanding officers and political commissars were shot, while its rank-and-file soldiers were given the option to either join the insurgent army or be stripped of their uniforms and sent home.

The insurgents set out from Huliaipole on a series of raids against the Red Army positions in northern Ukraine, taking 13,400 soldiers as prisoners of war, rendering a further 30,000 hors de combat and executing 2,000 political commissars and commanding officers.

[76] The continuous attacks against Red positions, combined with sustained propaganda efforts and the redistribution of property to the local peasantry, eventually resulted in more partisan detachments joining the Insurgents.

[80] On 25 May, the Bolshevik authorities of Katerynoslav province decided to re-focus local efforts on eliminating the resurgent Makhnovshchina, prioritizing anti-insurgent activities over the newly-established Committees of Poor Peasants and the requisitioning of food.

[84] As Red Army defections increased, the Bolshevik central command once again turned its attention towards the insurgents, with the Cheka's director Felix Dzerzhinsky even arriving in Katerynoslav province to personally direct the anti-Makhnovist campaign.

[107] Negotiators from both factions drafted the terms of a political-military agreement, which would extend civil liberties to Ukrainian anarchists in return for the military subordination of the Insurgent Army to the Bolshevik high command.

[110] The other Bolshevik signatory was Yakov Yakovlev, who denounced the Ukrainian anarchists at the first congress of the Red International of Labor Unions, blaming the breakdown of the alliance on the Makhnovists, who he labelled as "bandits".

[111] Despite the Bolshevik displays of Realpolitik, the Makhnovists hoped that the pact would continue to hold for another few months, which would allow them time to build a libertarian alternative to the Ukrainian Soviet government.

The Makhnovist delegation to the anarchist congress in Kharkiv, led by Dmitry Popov, bluntly declared the restoration of the free soviets and the autonomy of the Makhnovschina, calling on the Bolsheviks to fully implement the terms of the political pact.

[119] That same day, spies from the 42nd Rifle Division were discovered attempting to locate the exact whereabouts of the insurgent command, with the purpose of aiding a Red Army offensive against the Makhnovshchina.

[120] The delegation in Kharkiv responded by pressing Christian Rakovsky to arrest the 42nd Division's commanding officers and prevent any Red Army incursion into insurgent-held territory, but the Soviet government claimed it had all been a misunderstanding and promised to investigate it.

[143] The contingent's commanders announced "the return of the Crimean army", now only 1/5th of its original size, and told the story of Karetnik's assassination at a general assembly of the remaining insurgent forces.

With the Revolutionary Military Council putting pressure on Frunze and Kamenev to liquidate the insurgent movement, they ordered continual sweeps through insurgent-held territory over the subsequent weeks, planning to push them down towards the Sea of Azov, where they would be "ruthlessly exterminate[d]".

[146] But the Makhnovists continued to remain an ephemeral target, launching waves of surprise attacks against Red units and seizing their equipment, before breaking out of their encirclement with relative ease.

Surrounded by a much larger Red force, the insurgents managed to go on the offensive, breaking out to the north and escaping with their entire cavalry and almost all of their infantry after a day of constant fighting, in a battle that became known as the "Andriyivsky konfuz".

[157] The insurgents responded by splitting up into several small detachments and scattering throughout Ukraine,[162] abandoning their heavy weapons in order to stay mobile on the open steppe.

[166] Makhno himself led a detachment towards Yuzivka, but was turned back by a larger enemy force and retreated to Yelysavethrad, taking care to avoid the roads in order to make their pursuit more difficult.

[173] The Ukrainian Soviet government were increasingly worried by the persistence of the Makhnovist movement, with Eidemanis publishing several papers on how he thought the insurgency could be overcome, through both military and political means.

[183] In response to the outbreak of the Kronstadt rebellion in March 1921, Mykhailo Brova's detachment was dispatched to the Don and Kuban regions, while others were sent to Voronezh and Kharkiv, all in order to foment the further spread of the insurrection.

Makhno's detachment stuck to the banks of the Dnieper, eventually splitting up in order to cover more ground, in the face of continued Red Army assaults and ambushes.

Under Avksentevsky's command, the Red Army offensive against the Makhnovists was stepped up, with prominent Bolsheviks such as Roberts Eidemanis, Vasily Blyukher and Nikita Khrushchev taking charge of on-the-ground operations.

The subsequent pursuit of the Makhnovists lasted five days and covered 520 kilometers, causing the insurgents heavy losses and almost running them out of ammo, before they were finally able to shake the armored detachment off their trail.