In the second half of the fourteenth century Podillya gradually became a new historical region on the contested borders. Remaining under the influence of the Tatars for a long time, the subordination of the land to the Koriatovych brothers did not change perceptions of the territory. Defeated in the Battle of Blue Waters, three Tatar kings— Hadjibei, Kutlubuh, and Dmytro— had ruled over three parts of the vast region, stretching more than 500 kilometres east from the Dnieper and crossed by the main trade routes from that part of Europe. Echoes of this perception of the region found their reflections as late as the Battle of Grunwald in 1410.

In the 1360s the Koriatovyches founded the Principality of Podillya. It was one of the elements of the Grand Duchy of Lithuania's expansion, and the intention was to own a significant part of the Ruthenian lands, as well as to seize control over the socalled eastern trade in the Black Sea region, protecting the Grand Duchy from the Golden Horde's encroachments.

To a certain extent, this policy might have served the interests of the Gediminids, who tried to take control of the principalities of the Rurikids in the traditional way, through their large family. The Koriatovyches initially acted in line with this dynastic policy, but their collaboration with the Polish King Casimir III the Great led to them becoming the king’s, and the Crown’s, vassals (before 1366).

After the change of the dynasty, in 1370, the Koriatovyches faced, yet again, the dilemma of serving: either to serve a new king, Louis I of Hungary, or to return to the Gediminas dynasty. They chose Louis I of Hungary, a more powerful member of the House of Anjou, and his daughter Jadwiga, who occupied a higher position in the hierarchy. Their choice resulted in fatal consequences when Vytautas's army, having conquered Kamyanets— the last capital of the Principality of Podillya— forced Fedir and Vasyl Koriatovych, the last rulers, to seek refuge in the Hungarian Kingdom.

The deposition of the Koriatovyches from Podillya led to the partition of the region into three parts. The voivode of Kraków and starosta Spytek of Melsztyn from the family of arms of Leliwa received, oddly enough, a part of Podillya, along with the capital city of Kamyanets by the prince's right.