The Battle of Ilovaisk started on 7 August 2014, when the Armed Forces of Ukraine and pro-Ukrainian paramilitaries began a series of attempts to capture the city of Ilovaisk from pro-Russian insurgents affiliated with the Donetsk People's Republic (DPR) and detachments of the Russian Armed Forces. Although Ukrainian forces were able to enter the city on 18 August, they were encircled between 24 and 26 August by overwhelming Russian military forces that crossed the border, joining the battle. After days of encirclement, Ukrainian forces rejected the DPR's proposal to open a humanitarian corridor on the condition that they abandon their armored vehicles and ammunition, and on the morning of 29 August 2014 began to leave Ilovaisk with their weapons. The Russian side opened fire on the evacuating Ukrainian soldiers, many of whom died whilst trying to escape.

The Chief of the General Staff and Commander-in-Chief of the Armed Forces of Ukraine, Viktor Muzhenko, stated on 26 August 2016 that the cause of the battle's outcome was the involvement of Russian troops, along with Ukrainian commanders' incompetence in the planning of the retreat.Kyiv honoring soldiers killed in 2014 Ilovaisk battle, UNIAN (29 August 2016)

Events

Prelude

Since 11 July 2014, parts of Donetsk Oblast were shelled from Russian territory. On 23 July 2014, the brother of the Border Troops General Mykola Lytvyn, General Petro Lytvyn, was appointed the commander of sector D.Tynchenko, Ya. August 2014. Ilovaysk. Part I. Unjustified hopes for victory (Серпень 2014-го. Іловайськ. Частина І. Невиправдні сподівання на перемогу). The Ukrainian Week. 23 August 2015 Sector D consisted of the area between Donetsk city and the Russo-Ukrainian border. Ukrainian forces intended to cut off insurgent supply lines between Donetsk and Luhansk. At the same time, some units were involved in attempts to retake the Russo-Ukrainian border. The sector was to be managed by two battalions of the 30th Mechanized Brigade, one battalion from each 25th and 95th Airborne brigades and 51st Mechanized Brigade, Prykarpattia Battalion (composed of volunteers), and a company of the 28th Mechanized Brigade.

Soon after securing the area around the Savur-Mohyla hill (Amvrosiivka Raion and Shakhtarsk Raion), on 31 July 2014, a battalion of the 25th Airborne Brigade was sent to assault Shakhtarsk. During the attack, the battalion lost 26 soldiers and passed the city from East traveling North conducting a raid towards villages of Petropavlivka and . Two other battalions traveling past Torez and Snizhne were supposed to reach Miusynsk. Along the line, those two battalions, from the 30th and 95th brigades, lost communication with each other, but later the battalion from the 95th Brigade met up with the battalion of the 25th Brigade near Orlovo-Ivanivka and exited towards Ukrainian forces at Debaltseve.

On 11 August, the Ukrainian mass media portrayed the manoeuvre as a successful raid behind enemy lines; however, the results and purpose of it remain unknown. It is possible that the activities of Ukrainian airborne troops near the MH-17 crash site triggered the use of the regular armed forces of the Russian Federation.

On 6 August, the National Security and Defence of Ukraine announced that there was a possibility of a Russian military invasion and that Ukrainian army was prepared to stop it.Ukrainian army is ready to stop Russian aggression – NSDC (Українська армія готова дати відсіч російській агресії - РНБО). Ukrayinska Pravda. 6 August 2014 On 7 August 2014, the leader of the pro-Russian militants in Donetsk Oblast, Alexander Borodai, was replaced by Alexander Zakharchenko. Ukrainian troops made their first attempts to attack the city of Ilovaisk on 7 August 2014.

Over the next few days, Ukrainian forces made multiple attempts to enter the city, but were bogged down by heavy fighting with the insurgents.

Ukrainian forces enter Ilovaisk

Ukrainian forces attempted to enter Ilovaisk during the day on 18 August, but failed. Led by the Donbas Battalion, Ukrainian forces launched another attempt to storm the city on the night of 18–19 August. This attempt was successful, and they raised the Ukrainian flag over the city administration building without any casualties. Ukrainian media viewed this victory as an example of the strength and effectiveness of the government's "Anti-Terrorist Operation" (ATO) against the insurgents. As Ukrainian forces entered the city, Donbas Battalion commander Semen Semenchenko was wounded after being struck by mortar fire and was evacuated for medical treatment.

Following the flag-raising, the Internal Affairs ministry said that Ukrainian military, including the Donbas, Dnipro and Azov brigades, were clearing the city of "terrorists", specifically mentioning that they killed "a great number" of insurgents from the Oplot Battalion of the Donbass People's Militia. They also said that reinforcements from the National Guard of Ukraine were forthcoming. After a day of fighting, roughly fifty percent of Ilovaisk was under government control. Ukrainian forces also captured six insurgents, including one Serbian volunteer. Azov and Shakhtarsk battalions left the battle of Ilovaisk that day, heading to reinforce garrisons of Mariupol and Komsomolske cities respectively.

On the following day, 20 August, Ukrainian forces claimed they had taken complete control of Ilovaisk. DPR officials denied this, and declared that they remained in control. Over the course of the day, Ukrainian forces fought off numerous insurgent counter-attacks. Street battles took place across the city, and at least nine Ukrainian soldiers were killed in the fighting. Following this, the Donbas Battalion requested reinforcements.

By 21 August, amidst the heavy and constant fighting, the Internal Affairs ministry stated that twenty-five percent of those from volunteer paramilitary battalions killed since the ATO began were killed in Ilovaisk. No reinforcements for Ukrainian forces arrived. According to commander Semenchenko, some members of the Donbas Battalion were killed when insurgents flying the Ukrainian flag attacked an ambulance. Semenchenko described this act as "medieval savagery". He also said that the Donbas Battalion had been "abandoned" by both the Ukrainian government and the other volunteer paramilitary battalions, both of which largely had withdrawn from the city.

Encirclement of Ukrainian troops; Ilovaisk under siege

The remaining Ukrainian forces in Ilovaisk became completely encircled by DPR insurgents and Russian reinforcements on 24–26 August, and the fighting continued to take its toll. Ukrainian soldiers started seeing Russian regular army troops on 24 August, and their presence increased over the next few days.

On 24 August at around 12:15, a column of BMD-2s for the Russian 331st Airborne Regiment was hit by a Ukrainian anti-tank squad of the 51st Mechanized Brigade near Kuteinykove settlement. Two BMD-2's were destroyed. The paratroopers left their vehicles and took cover in trees nearby. Several hours later, around 5 pm, they left their cover and were captured by the reconnaissance group of the 51st Mechanized Brigade near Dzerkalne village, the Ukrainian battalion tactical group's field headquarters. Ten paratroopers were captured.

On 26 August, a T-72B3 tank of the 6th Tank Brigade was captured by Ukrainian troops of the 51st Mechanized Brigade in a fight near Ahronomichne village. The captured tank took part in another fight that day near Mnohopillya village where the Russian column of mixed units from the 8th Mountain Brigade and 31st Air Assault Brigade were ambushed by the Ukrainian anti-tank artillery squad of the Ukrainian 51st Guards Mechanized Brigade. Two soldiers of the 31st Air Assault Brigade and one wounded soldier of the 8th Mountain Brigade were captured by Ukrainian forces.

According to the DPR, a large number of Ukrainian soldiers and paramilitaries were trapped in the town. During the fighting, the Ukrainian commander of the Dnipro Battalion suffered a concussion, while the commander of the was killed. In response to commander Semenchenko's pleas, many Euromaidan activists in the Ukrainian capital Kyiv protested what they saw as the government's "abandonment" of the volunteers fighting against the insurgents. Repeated artillery barrages launched by insurgent forces from nearby villages caused heavy casualties amongst the trapped Ukrainian forces.

Attempt to free encircled forces

The Ukrainian command attempted to free the encircled forces near Ilovaisk. The company tactical group was formed from 92nd Mechanized Brigade and had 276 soldiers, four tanks, three SPGs and 10+ IFVs. It was sent from Kharkiv Oblast to Ilovaisk on 24 August 2014, after it became clear Russian military forces were approaching Ilovaisk. The unit was supposed to meet an assault squad from the Rukh Oporu Battalion and attempt to breach the Russian encirclement. Rukh Oporu squad had 90 soldiers and was equipped with two IFVs.

The 92nd Brigade's company arrived on 27 August in Komsomolske and continued to advance towards Ilovaisk. The column stopped for the night and shortly after was hit by heavy artillery shelling. The next morning it was completely defeated by Russian paratroopers, losing most vehicles but with relatively low troop casualties, with eight dead and several missing. The same fate met the Rukh Oporu squad, which was defeated on the morning of 28 August nearby, meaning the units were never able to rendezvous.

Ukrainian forces retreat and massacre

After days of being under siege in Ilovaisk, commanders of Ukrainian forces in the city attempted to negotiate an agreement that would allow them to withdraw from the city. Russian president Vladimir Putin said in the early morning on 29 August that a "humanitarian corridor for besieged Ukrainian soldiers" should be established, allowing the trapped soldiers to leave Ilovaisk. DPR prime minister Alexander Zakharchenko said he had agreed to open a humanitarian corridor on the condition that the Ukrainian forces leave their armoured vehicles and ammunition behind. These proposals were not accepted by the Ukrainian military command, and on 29 August at 06:00, Ukrainian forces began to move out of Ilovaisk in a column of sixty vehicles. At 8:00, Ukrainian forces regrouped at Mnohopillya, just south of Ilovaisk proper, forming two columns, and prepared to withdraw. The northern column, commanded by General Ruslan Khomchak, consisted of forces from the 17th Tank Brigade, 51st Mechanized Brigade and police units and had four tanks, several IFVs and approximately 1000 troops. The southern column, led by Col. , was formed from forces of the 93rd Mechanized Brigade and Donbas Battalion; it had two tanks, including a captured Russian T-72B3, a couple of IFVs, and roughly 600 troops.

The northern column advanced along the corridor, about an hour's drive, but was then surrounded by Russian and insurgent troops. At the village of Oleksandrivka, two T-72BAs and an IFV of the Russian 21st Motor Rifle Brigade were destroyed in a clash with Ukrainian forces. Near the Krasnaya Polyana valley Russian troops opened fire on the northern column with mortars and heavy machine guns, splitting it in two. The front half of the column, with tanks, headed to the village of Novokaterynivka, while the rear half was obliterated, with six IFVs and multiple cars of police units destroyed.

That valley had a battery of D-30 howitzers of the Russian deployed. Several trucks of the regiment were destroyed near the artillery positions. The armoured head of the column reached Novokaterynivka, where several dug-in tanks and IFVs were spotted by Ukrainian tankers of the 17th Tank Brigade. After a brief clash, all four Ukrainian tanks and IFVs were destroyed. Some crews were able to leave vehicles, and 42 Ukrainian soldiers made it out of the encirclement and reached Ukrainian positions.