A few years later, the brotherhood of the Monastery added a new-martyr to its ranks. The Great Martyr Gideon, who had been forced to change his religion at a young age. Repenting this decision, he was tonsured as a monk at the Monastery, which he left to voluntarily seek martyrdom on 30 December 1818 in Turnavo, Thessaly. The residents of Turnavo sent a part of his holy relics to the Monastery. The brotherhood of the Monastery also includes the Holy Gervasios blessed by Christ the Saviour, who for years lived as a ragged ascetic around the Monastery, where he died peacefully in 1820. As a result of the outbreak of the Greek Revolution in 1821 and the unsuccessful uprising in Macedonia, the Monastery, along with all the monasteries on the peninsula, were negatively affected during the following years. Ottoman troops set up their base camps in the monasteries, which were forced to provide for their needs. a heavy, special tax was levied collectively on the monasteries, and the regular taxes were doubled. The dependencies in Chalkidiki sustained great damage, the debt increased enormously, and a large number of monks abandoned Mt Athos. Between 1823-1830, less than 1,000 monks still remained on the peninsula. For a period of five years, Karakallou suffered losses to its dependencies in Chalkidiki and in Strymona, experienced a crisis, and no structural work was undertaken at the Monastery. After 1830, communication with the dependencies was re-established, the economic situation gradually improved, and the number of monks began to increase. Around 1835, it is possible that the Monastery faced an economic crisis because of its debts, as a result of which they were forced to pawn vestments and artefacts, while in 1836, the British traveller R. Curzon removed at least 16 valuable manuscripts from the library.
It is known that in 1854, Damaskinos, the Abbot of Katakallou, gave a beautiful horse to the military leader Tsami Karataso, an action which caused him to lose his position and to expelled from the Monastery. Moreover, during the second half of the previous century, the Monastery began to have major problems with its property rights: In 1863, the Romanian government confiscated all the dependencies of the eastern Greeks in Moldovlachia, among them being the dependencies of Karakallou, and populated the Monastery with many Russian monks for the purpose of taking control of it. Relevant information indicates that the foreign monks first lived in the dependencies, which they planned to transform into cenobitic sketes, and from there to later enter inside the Monastery itself. In the end, their goals were not achieved: After the liberation and incorporation of Mt Athos into the Greek nation, the Karakallou does not appear to have fallen into decline. However, the economic problems worsened when, after 1922, the holdings of the Athonite monasteries in Macedonia and the islands of the North Aegean were expropriated and given to the refugees from Asia Minor.
