Ioannina in 1318 and broke away from Arta. In the same year, Ioannina became tributary to the Byzantine emperor Andronikos II Palaiologos (r. 1282–1328). The city was elevated to a metropolitan bishopric, and in 1319 Andronikos II issued a chrysobull conceding wide-ranging autonomy and various privileges and exemptions on its inhabitants.
In 1337–1340, Andronikos III Palaiologos (r. 1328–1341), aided by John Kantakouzenos, dissolved the Despotate of Epirus and Ioannina became once again part of the Byzantine Empire. A few years later however it fell to the Serbs, who had, by then, expanded their state over much of Byzantine and Bulgarian territory to form the Serbian Empire. The city's privileges were also honored by the Serbs, and as a result Ioannina rose to economic and cultural prominence over the next century. The city flourished, becoming an important financial and cultural center. During the Byzantine times it was referred to as the "metropolis of knowledge".
The city was the capital of the restored Despotate of Epirus from 1358 to 1416. In 1366/67 the Serb Thomas II Preljubović became the new overlord of Ioannina, under whose rule the city stood against Albanian attacks. After Preljubović's death in 1384, the city surrendered to Esau de' Buondelmonti (1385–1411) and Carlo I Tocco (1411–1430).
Early Ottoman period (1430–1647)
The death of Tocco in 1430 signaled the submission of Ioannina to the Ottoman Turks who granted several privileges to the town in exchange for its surrender. These were known as the Rule of Sinan Pasha, from the name of Kara Sinan Pasha, who signed the treaty. Ioannina became a seat of the Ottoman Sanjak of Ioannina.
In 1611 the city suffered a serious setback as a result of a peasant revolt led by Dionysius the Philosopher (aka Skylosophos), Bishop of Larisa. The Greek inhabitants of the city were unaware of the intent of the fighting as previous successes of Dionysios had
