It is located on the slopes of the Osogovo mountains, near Kriva Palanka. According to some stories its founder was Joakim Osogovski, an anchorite who lived in the XI century. It is also possible that it was built after his death. In the records of his life it was written that during the Byzantine Emperor Manojlo Omnen /1143 - 1180/, a priest Theodore from Ovce Pole, after entering the monastic order and being given the monastic name of Theofan, founded the monastery. He later became its first prior and built a church dedicated to Joakim Osogovski, where he buried the hermit's ashes. In the historic sources the monastery is first mentioned during the Bulgarian Tzar Kalojan /1196 - 1207/, who visited it. In the "Karlovac Chronicle" there is a record that around 1305 King Milutin built a church dedicated to St. Joakim, yet maybe he only renovated it. It is believed that one of the renovators was also K. Dejanovic Dragas. In 1330, before the battle of Velbuzd with the Bulgarian Tzar Sisman, Stefan Decanski visited the monastery to say his prayers before St. Joakim's relics. There is also a record of it in 1350. In 1436, on his way to conquer Bosnia, the Turkish Sultan Mehmed II came to the monastery. In the second half of the XV century, the monastery sought support from the Republic of Dubrovnik. On 19th December 1474, the Republic of Dubrovnik's Council endowed it 20 perperi (the then golden money). In 1489 the prior of the monastery was Arsenie. In the Sarajevo Museum the monastery's chronicles for 1463, 1487, 1491, and 1492 are kept. In the monastery the book "The Life of Grigorie Omiritski" was written, probably in 15 - 16 century. In 1585 the monastery was destroyed during an earthquake. Throughout the XVII century it was economically sound and had well developed monastic life. At the end of a hand-written Gospel, there is a signature of a Patriarch Arsenie, who noted that he visited the monastery in 1686. In 1690 the Turks ruined it. Also around the mid-XVIII century it was in a bad shape. It will revive in the mid-XIX century, i.e. in 1847 when, initiated by Hadzi Stefan Beglikcija from Kriva Palanka, the construction of a large cathedral church of St. Jovan Osogovski started. It was finished and consecrated in 1851.
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