When Vytautas escaped to the Teutonic Knights in 1382, Ivan followed him and Jogaila took away his estate. However, as Vytautas and Jogaila reconciled few years later, Ivan gifted Jogaila with a golden belt and received his estate back. Ivan followed Vytautas when he escaped to the knights once again in 1390 during the Lithuanian Civil War. In 1391 Ivan escorted Sophia, the only child of Vytautas, to Moscow where she married Vasili I of Russia. After Vytautas gained a powerful ally in the east, Jogaila agreed to make peace and Treaty of Astravas was signed in 1392. Ivan became the right hand of Vytautas, and after Skirgaila death, he ruled Kyiv as viceregent.