While the Balkan states were exhausting their strength in feudal disunity and rivalries (there existed by the middle of the 14th century 40 independent feudal possessions in the Balkans), stormy clouds appeared from Asia, ominously threatening the Balkan peoples. The beginning of the 14th century marked the onward march of the Ot-toman Turks. In 1352 they captured the Tsimpe stronghold on thq Gallipoli Peninsula and two years later the Gallipoli fortress, thus placing the Dardanelles under their control. The Byzantine Emperor offered to Serbia and Bulgaria to act in concert against the invaders, but they turned a deaf ear to his desperate appeals. During the 1360s Sultan Murad I conquered the whole of Eastern and part of Northern Thrace, including the big cities of Plovdiv and Stara Zagora.
The local population, left without protection by the Byzantine government, organized its defence on its own. The Bulgarian feudal lord Momchil rejected the suzerainty of the Byzantine Emperor and established his rule over the entire Rhodope region and part of the Aegean coast. Momchifs several big victories over the Ottomans won him great popularity and his fame rivalled that of Ivailo before him. His army consisted not only of men from the regions directly afflicted by Turkish incursions but also of discontented peasants from all over Bulgaria. Constantinople became even more afraid of Momchil's men than of the Turks. A Byzantine-Turkish alliance against the rebellious boyar was hastily concluded and the small state of Momchil, who had risen to the position of a genuine popular leader, was wiped away.
After Momchil, two feudal lords from Macedonia – Vukashin and Ouglesh – decided to cross swords with the Ottomans but they were utterly defeated in a battle near Chernomen, not far from Adrianople, and fell in that battle, after which Murad I advanced to the north and northeast, entering the territory of Bulgaria. Here, however, the conquerors came up against unexpectedly strong resistance put up not so much by the troops of the Tsar as by local commanders of strongholds and by the population itself. The Ottomans needed moie than ten years to traverse the route between Plovdiv and. Sofia. The cities of Yambol, Karnobat, Sofia, Bitola, the strongholds in the Rhodope Mountains of Tsepena and Rakovitsa and many others put up particularly strong resistance. Sofia fell in 1382, only after the Turks had managed by deceit to take prisoner Ban Yanuka, the extremely capable Leader of its defence. With the hope of preventing the further penetration of the Turks into Bulgaria, Tsar Ivan Shishman became vassal to Murad I.
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