During the Khmelnytsky Uprising Terebovl became one of the centers of the struggle in Podolia lands. The city was frequently raided by the Crimean Tatars, Turks and their erstwhile allies, the Zaporozhian Cossacks. The most destructive attacks happened in 1498, 1508, 1515 and 1516, resulting in a temporary decline of the town. In 1674, as part of preparations for another war with the Turks, who at that time were at war with Russia, the Diet decided to further strengthen Terebovlia and send garrisons there. The following year the Janissary once again embarked on raids against towns and villages, and on 20 September 1675 destroyed the town, but the castle was held by a small group of defenders (80 soldiers and 200 townsmen) until King Jan III Sobieski arrived to relieve them. This episode is known as the Battle of Trembowla. The castle was destroyed during the final Turkish invasion of 1688.
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