It is not known exactly when the monastery was founded. Today's see of the Eparchy of Mileševa was established before the 1465 Ottoman conquest of the city. Since the Ottoman law forbade the building of new churches, but permitted the rebuilding of those which had existed at the time of Mehmed the Conqueror, it is certain that a church had existed on the site of the present monastic church, before the Ottoman conquest and probably made of wood. The first reference to Holy Trinity Monastery in Pljevlja dates from 1573, when Sava, a monk from the monastery, copied a manuscript. At that time the monastery was managed by abbot Visarion, who took great pains to improve its economic position. Moreover, an inscription published by Sava Kosanović in 1871 shows that it was precisely this abbot who restored the monastery. This testimony is corroborated by the donor's portrait of Visarion on the south wall of the nave. On 1 December 1941, during the Battle of Pljevlja the Communist forces killed Serafim Džarić, an archimandrite of the Monastery of the Holy Trinity of Pljevlja, as a direct consequence of the order of Partisan headquarters to start with "fierce struggle against spies and fifth column" after the capture of the town.