Vasily Mikhailovich was inducted into the military as a private in 1735 at the age of 13, where he gained his first combat experience fighting under Field Marshal Burkhard Christoph von Münnich in the Crimea.

Anna simply replied to her general, "Do not take away my sword from this suckling", and so Vasily Mikhailovich became the only member of his entire noble clan to be exempted from the ban during her ten-year reign.

In 1741 he would be made a captain, and by 1745 would be a lieutenant-colonel and adjutant to his now rehabilitated uncle Vasily Vladamirovich, who had been appointed president of the Collegium of War, the body that oversaw the entire Imperial Army.

According to the recollections of Prince Yakov Shakhovskoy, which he cited from his personal notes,[4] Dolgorukov conspicuously studied from his fellow commanders to improve his knowledge of military affairs.

Towards the end of this campaign Dolgorukov was wounded in the leg by canister shot, and had to seek treatment for his injury, but the General recovered in time to lead an infantry brigade at the Kunersdorf.

In 1771 he was sent to conquer the Khanate: on June 25 he captured the fortifications of the Isthmus of Perekop, on July 10 he defeated the Tatar-Turkish army (95,000) at Kefe (now Feodosia); after this victory the Turks left the towns of Arabat, Yeni-Kale, Kerch, Balaklava and others.