Dragota's Uprising

Dragota's Uprising of 1255 was an attempt by the Bulgarian population of Melnik and its surrounding region to rise against the authority of the Empire of Nicaea. Dragota, commander of the Melnik garrison and a former Bulgarian governor of Serres, decided to rebel against Nicaean rule.
He gathered troops from Melnik and nearby areas and besieged Melnik Fortress. Despite his efforts, the Nicaean garrison successfully defended the fortress and repelled his attacks. Meanwhile, Emperor Theodore II Laskaris of Nicaea set out towards the region to suppress the uprising.
Dragota fortified the Rupel Gorge and built a defensive barrier, guarded by a large army. The considerable military strength he displayed suggests that he may have received support from the Bulgarian tsar Michael II Asen. Nevertheless, the uprising received no support from Tarnovo, contributing to its failure.
The Nicaean operations included successfully outflanking the Bulgarian fortifications in the Rupel Gorge. After this manoeuvre, Nicaean troops attacked the gorge's defenders, also launching a frontal cavalry assault. The Bulgarians scattered and won, while Dragota was severely wounded and died three days later.
After the defeat, Emperor Theodore II Laskaris entered Melnik, which surrendered without a fight. The rebels' property was confiscated, and their wives and children were taken captive. Melnik remained under Nicaean control for around one hundred years.

The uprising ended in failure for the Bulgarian side, and the Melnik region remained part of the Empire of Nicaea for some time afterwards.