The monastery greatly prospered until the Ottoman conquest. Many Byzantine emperors, such as John V Palaiologos, contributed to this prosperity, as did other Orthodox rulers such as Serbian Emperor Stefan Dušan and Serbian Despot Đurađ Branković. This prosperity was however shrouded by constant disputes over land issues with the neighboring Vatopediou monastery, as well as by many pirate raids and two great fires that damaged the monastery during the 14th century. According to manuscripts held in the monastery's collection, the pirates posed a serious threat to the monastery because the sea near it is usually calm compared to the seas around the rest of the Athonite peninsula. Because of these reasons the monastery was eventually ruined and practically deserted which allowed the nearby monasteries of Hilandar and Zograf to grab various portions of land from it, which led to further legal disputes.