After the
occupation of Kharkiv by the
Bolsheviks, the
Red Guards and sailors of the
Black Sea Fleet were tasked with capturing
Synelnykove and
Oleksandrivsk, which were important railway junctions in the region. Facing reports that 8,000 heavily armed Bolsheviks were advancing towards Synelnykove, with the aim of cutting off Ukraine from the
Don Host,
Symon Petliura ordered that the railway track in Oleksandrivsk be dismantled and the city's sailors be detained. On , Petliura began transferring his troops of the
Ukrainian People's Army (UPA) to
eastern Ukraine, in order to maintain its connection with its allies in the Don Host. This alarmed local Bolsheviks, led by
Vladimir Antonov-Ovseenko, who desperately attempted to establish a defensive line through the region, marking the capture of Oleksandrivsk as a necessity to prevent the UPA from linking up with the Don Cossacks. On , the Red Guards captured
Lozova and began advancing on Oleksandrivsk. By this time, a conflict between the local Bolsheviks and the Ukrainian authorities was already brewing in Oleksandrivsk, with 40
Free Cossacks, 13 UPA soldiers and a dozen officers facing off against 300 Red Guards. 250
Haydamaks of the 3rd Haydamatsky Kuren were sent from
Katerynoslav to reinforce the city's garrison, with whom they captured a number of armored vehicles from the Bolsheviks of the 3rd Rear Auto Repair Shop. On , the Bolsheviks captured Synelnykove and began preparations to attack Oleksandrivsk. ==Battle==