Unlike most other dukes, after the collapse of the First Serbian Uprising in 1813, he did not flee across the Sava and the Danube, but together with his father Milija surrendered to the Grand Vizier Hurshid Pasha. Hurshid Pasha did not want to execute them but in 1814, Ćaja-paša in his zeal had Milosav's father liquidated, and then impaled his head and placed it next to other heads of Serbian insurgents in front of the Belgrade's Stambol Gate. Due to his father's death, Milosav, with the support of Belgrade's Metropolitan Dionysius, fled from Belgrade to Resava, where he prepared for a new uprising in 1815. During the Second Serbian Uprising, together with the insurgents, he fought against the Turks in the battle of Ranovac, as well as during the Turkish attack on Miliva.