After the killing of his father by the servants of the magnate Kalinowski he moved with his mother to Ostroh where his elder brother was a seminary student.

He left the service in 1594, and organized a paramilitary unit of unregistered cossacks in the vicinity of Bratslav, and raided several Moldavian and Hungarian towns.

The following year, Nalivaiko's Cossacks were joined by many run-away Ukrainian peasants and captured the town of Lutsk where his men massacred Polish nobility, Catholic clergy and local Greek-Catholics.

[1] Nalivaiko eventually offered peace to the Polish king Sigismund III Vasa, conditioned that the Poles cede the lands between Southern Buh and Dniester rivers south of Bratslav to the Cossacks in exchange for their military service and loyalty to the Polish–Lithuanian Commonwealth.

Having refused these terms, the king recalled Stanisław Żółkiewski from Moldavia to quell the Nalivaiko Uprising, which had engulfed most of Polish crown lands in Ukraine and Belarus (that time called Ruthenia) by 1596.