The siege of Sofia occurred either in 1382 or 1385 as part of the ongoing conflict between Bulgaria and the Ottoman Empire. In 1373, Bulgarian Emperor Ivan Shishman, recognizing the Ottoman strength, entered into a vassalage agreement and arranged for his sister Kera Tamara to marry Sultan Murad I in exchange for the return of some conquered fortresses.

Despite this peace agreement, in the early 1380s, the Ottomans resumed their military campaigns and besieged the strategically important city of Sofia, which controlled vital communication routes to Serbia and Macedonia. Unfortunately, historical records of the siege are scarce. Initially, the Ottomans made unsuccessful attempts to breach the city's defenses, leading their commander, Lala Shahin Pasha, to consider abandoning the siege.

However, a Bulgarian traitor managed to lure the city's governor, Ban Yanuka, out of the fortress under the guise of a hunting expedition, resulting in his capture by the Turks. With the Bulgarians left leaderless, they eventually surrendered. The city's walls were dismantled, and an Ottoman garrison was stationed there. This victory allowed the Ottomans to advance further north-west, ultimately capturing Pirot and Niš in 1386, thereby creating a barrier between Bulgaria and Serbia.