In 1556 in service to Ivan the Terrible he helped lead two raids of Ukrainian Cossacks and Russians against the Crimean Tatars around Ochakiv. In 1558 he raided around Perekop. In 1559 he raided down the Donets and Don. With the start of the Livonian War, Ivan turned his attention west and Vyshnevetsky, being Ivan's close relative and his governor in the North Caucasus, returned to the Lithuanian service with a great number of his Adyghe warriors. His detachments became the major military force of the Polish-Lithuanian Commonwealth in centuries to come. In 1561, at the request of the Lithuanian prince, he went back to fortifying Khortytsia.