Nestor Makhno in the context of "Ukrainian War of Independence"

Crimea in the five years after the Russian Revolution had a large number of governments culminating in being a stronghold of anti-Communist forces and the place on Russian soil where they made their last stand.

Following the Russian Revolution of 1917, the military and political situation in Crimea was chaotic like that in much of Russia. During the ensuing Russian Civil War, Crimea changed hands numerous times and was for a time a stronghold of the anti-Bolshevik White Army. It was in Crimea that the White Russians led by General Wrangel made their last stand against Nestor Makhno and the Red Army in 1920. When resistance was crushed, many of the anti-Bolshevik fighters and civilians escaped by ship to Istanbul.

Anarchism in Ukraine has its roots in the democratic and egalitarian organization of the Zaporozhian Cossacks, who inhabited the region up until the 18th century. Philosophical anarchism first emerged from the radical movement during the Ukrainian national revival, finding a literary expression in the works of Mykhailo Drahomanov, who was himself inspired by the libertarian socialism of Pierre-Joseph Proudhon. The spread of populist ideas by the Narodniks also lay the groundwork for the adoption of anarchism by Ukraine's working classes, gaining notable circulation in the Jewish communities of the Pale of Settlement.

By the outbreak of the 1905 Revolution, a specifically anarchist movement had risen to prominence in Ukraine. The ideas of anarcho-communism, anarcho-syndicalism and individualist anarchism all took root in Ukrainian revolutionary circles, with syndicalism itself developing a notably strong hold in Odesa, while acts of anarchist terrorism by cells such as the Black Banner became more commonplace. After the revolution was suppressed, Ukrainian anarchism began to reorganize itself, culminating in the outburst following the February Revolution, when Nestor Makhno returned to the country and began to organize among the peasantry.

The Makhnovshchina (Ukrainian: Махновщина, romanized: Makhnovshchyna, IPA: [mɐxˈnɔu̯ʃtʃɪnɐ]) was a mass movement to establish anarchist communism during the Ukrainian War of Independence of 1917–1921. Named after Nestor Makhno, the commander-in-chief of the Revolutionary Insurgent Army of Ukraine, its aim was to create a system of free soviets that would manage the transition towards a stateless and classless society. It controlled territory in southern and eastern Ukraine.

The Makhnovist movement first gained ground in the wake of the February Revolution, when it established a number of agricultural communes in Makhno's home town of Huliaipole. After siding with the Bolsheviks during the Ukrainian–Soviet War, the Makhnovists were driven underground by the Austro-German invasion and waged guerrilla warfare against the Central Powers throughout 1918. After the insurgent victory at the Battle of Dibrivka, the Makhnovshchina came to control much of Katerynoslav province and set about constructing anarchist-communist institutions. A Regional Congress of Peasants, Workers and Insurgents was convened to organise the region politically and economically, with a Military Revolutionary Council being established as the movement's de facto executive organ.

The Revolutionary Insurgent Army of Ukraine (Ukrainian: Революційна Повстанська Армія України, РПАУ, romanized: Revoliutsiina Povstanska Armiia Ukrainy, RPAU; abbr. RIAU), also known as Makhnovtsi (Ukrainian: Махновці), named after their founder Nestor Makhno, was an anarchist army formed largely of Ukrainian peasants and workers during the Russian Civil War. They protected the operation of "free soviets" and libertarian communes by the Makhnovshchina, an attempt to form a stateless anarcho-communist society from 1918 to 1921 during the Ukrainian War of Independence.

Huliaipole (Ukrainian: Гуляйполе [ɦʊlʲɐjˈpɔle]; lit. 'walk-about field') is a small city in Polohy Raion, Zaporizhzhia Oblast, Ukraine. It is known as the birthplace of Ukrainian anarchist revolutionary Nestor Makhno. In January 2022, it had an estimated population of 12,786.

Huliaipole was attacked by Russian forces during the Russian invasion of Ukraine and sustained heavy damage, placing it on one of the lines of contact separating Ukrainian and Russian forces.

The Battle of Dibrivka was a military conflict between Ukrainian insurgents, led by Nestor Makhno and Fedir Shchus, and the Central Powers that were occupying southern Ukraine. It took place on 30 September 1918, towards the end of World War I. The battle began when Makhno, Shchus, and a group of anarchist supporters ambushed Austrian and Ukrainian detachments stationed in Dibrivka. The anarchists were armed with machine guns and were assisted by local peasants, who together captured ammunition, arms, and prisoners of war. It resulted in an insurgent victory and the establishment of an autonomous territory in the region, following the subsequent defeat of the Central Powers.

Semen Mykytovych Karetnyk (Ukrainian: Семе́н Мики́тович Каретник; 1893 – 1920) was a Ukrainian anarchist revolutionary and military commander in the Revolutionary Insurgent Army of Ukraine (RIAU). He often replaced Nestor Makhno as supreme commander of the Insurgent Army in 1920. Karetnyk gained a reputation for his central role in defeating the White Army in Crimea in November 1920.