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The situation after the ignition of the Greek revolution and the failure of the rebellion in Macedonia in 1821 influenced the Monastery of Karakallou as well as the whole of Mount Athos. Turkish troops settled in every Monastery and demanded the cost for their living. Extra taxes were imposed and regular taxes doubled. The metochia of Halkidiki suffered heavy damages, the debts swelled and a large number of monks left Mount Athos. Between 1823-1830, less than 1,000 monks remained in Mount Athos. For a period of five years the Monastery suffered damages to its metochia in Halkidiki and Strymon. After the retreat of the Turkish troops in 1830, communication with the metochia was restored, the economic situation gradually improved and the number of monks began to increase. As is known, in 1854 the abbot of the monastery Damaskinos of Karakallou, donated to the chieftain Tsamis Karatasos a nice horse, an act that eventually caused him to lose his authority and to leave the Monastery.

Since the 16th century, the Monastery, like many others, had functioned as an idiorhythmic community. In July 1813, a declaration by its Great Assembly announced the decision of the Karakallos Monastery to readopt the cenobitic system of monastic life, with the hieromonk Nektarios from the Ascension cell as the new Abbot. The transition to the cenobitic mode was consolidated by the patriarch Kyrillos VI's sigillion issued in the same year.

Despite its losses during the Ottoman era, the Monastery continued to retain ownership of its Byzantine dependencies. In fact, new estates that the Monastery had not had in the Byzantine period now appeared among its possessions: Chalkidiki (Ierissos, Kassandra, Ormylia, Sidirokaussia), Strymon (present day Nea Kerdylia, etc.), the islands Thassos, and Agios Efstratios in the North Aegean, and other dependencies in Crete, Asia Minor and Bessarabia. According to C. Pavlikianof, in 1535, Suleiman the Magnificent issued a firman (i.e., an official Ottoman decree) that authorized the voevoda (prince) of Moldavia and Wallachia to restore the Monastery's buildings without expanding them. Perhaps this edict refers to the maritime tower and the barbican (i.e. defensive fortification), which according to an inscription was completed when Germanos was Abbot, with the sponsorship of the Prince John Peter (perhaps Peter IV Rares of Moldova) and a monk named Joasaf.
According to Smyrnakis, in 1548, an Ottoman officer named Ibrahim ordered two Muslims, Mustafa and Ali, to visit Karakallos Monastery to measure the cathedral before its restoration was allowed, as was finally the case.
In 1708, Komnenos writes that in the 16th century, the Monastery was renovated at the expense of two generous sponsors: The Prince Neagoe Bassarab of Wallachia, and a prince named Peter. In fact, according to P. Androudis, the impressive tower has typical features of the 16th century, indicating it might have been one of the structures included in the above-mentioned work.
In the 17th century, Artchil, the King of Iberia, together with his brother George Vachtags (1674) and the monk Joashaff in the 18th century, played an active role in the Monastery, which grew considerably during that time: According to some testimonies, the population of monks practising in the Monastery and its dependencies reached several hundred.

Two hundred years later, in the the 16th-century Ottoman era, another great ascetic lived at the boundary of the Karakallos Monastery: St Dionysios of Olympus. According to his what is known about his life, around the year 1520, he retired to a skete of the Monastery, built a cell and the church of the Holy Trinity, and practised asceticism for several years. After a pilgrimage to Jerusalem, he returned to his skete and built the church of the Holy Fathers, before being elected Abbot of the neighbouring Monastery of Philotheou.

From the beginning of the 14th century, the Monastery and its environment lived the mystical experience of hesychasm with great ardor, as suggested by the relationship with Patriarch St Athanasios I with it. Particularly important was the time of the Abbot Hyakinthos Kerameus (1310-1333), when great ascetics were associated with the Monastery, among them being the Patriarch Philotheos Kokkinos, a former monk of Athos. In the Life of St Germanos written by the Patriarch, he describes the physical and spiritual environment of the monks and the Monastery. In fact, from 1322-1324, the young St Grigorios Palamas (who later went on to become an official defender of hesychasm) lived near the hermit Grigorios Drimys in the skete of Glossia, a dependency of the Monastery.

In 1287, a dispute on border issues erupted into a long-standing conflict between the monasteries of Karakallos and Great Lavra, which was to continue until the end of the 16th century. It is likely that this situation created the need for the 1294 chrysobull by the Emperor Andronikos II Palaiologos, which is preserved in the archives. It is the oldest document that describes the Monastery's property, its dependencies, and estates both in and outside Mt Athos. It shows an image of economic and demographic growth after a period of serious hardship. The introduction of the chrysobull refers to the many beneficial interventions by the Patriarch Athanasios I to the Emperor for the issuing of decrees in favour of the Karakallos Monastery, where he formerly resided. Although unknown from other sources, the information is considered accurate, since the emperor had a close friendship with Athanasios, and personally knew his earlier monastic life on Athos. Hence the Patriarch Athanasios, an enlightened and austere ascetic, a supporter of orthodoxy and consistency in the observance of the monastic rules, used to live in the Karakallos Monastery, perhaps on his second stay on Mt Athos, around 1278.

At the beginning of the 19th century, St Nikodemos Hagiorites is reported to have seen a very old imperial seal of the Emperor Romanos IV Diogenes (1068-1071), 'I saw a damaged sigillion by the Emperor Romanos IV Diogenes, on which the seal had representations of the king Romanos and the queen Eudokia with two children protected from above by Jesus Christ. On the back of the seal, there was a cross and some capital letters. According to what I was able to read from this very worn sigillion, it was validating the possession of lands that were dedicated centuries ago.' It was last seen and described in 1867 by Victor Langlois. In 1903, Smyrnakis writes that the sigillion had become lost, but its seal remained. However, he describes a different seal, as Kriton Chrysochoidis recently observed, the same as the one visitors can see today in a display case in the library: On the front, Christ is depicted standing between Romanos and Evdokia and crowning them; the three sons of Eudokia from the previous emperor Constantine I – Constantine, Michael (who later became Emperor), and Andronikos – are depicted on the reverse. Unfortunately, the content of the sigillion has not been preserved.

For the entirety of the medieval period until the end of the 15th century, the archives of the Karakallos Monastery have only seven documents. It is by far the smallest collection in a Monastery on Athos. The oldest document is only from 1294, and three more documents are preserved for the period 1568 to 1600. Professor Cyril Pavlikianov who studied them notes that fortunately there are some surviving interesting Greek, Slavic and Western references of the 18th and 19th centuries to compensate for the lost content of the archives of Karakallos.

Various speculations have occasionally been made about the origin of the Monastery's name. One connects it to the Roman Emperor Caracalla (188-207), perhaps through some unknown ruin or toponym. In fact, a popular legend, which misled the painter of the cemetery chapel, presents him as the Monastery's founder, adding an ironic hint to the anachronism, since Caracalla was a well-known persecutor of the Christians. Another suggestion that the owner was called Karakalos is made by the Patriarch Philotheos Kokkinos, who had lived on Athos in the 14th century, in his work The Life of St Germanos Maroulis. This name, however, does not occur earlier than the end of the 13th century, when it is known to be the name of the bishop of Nicomedia (1289-1309). Smyrnakis mentions in 1903 that Nikolaos from the village of Karakalla and the family of Karakalla, who was converted to Christianity during the years of Athanasios of Athos, is celebrated as the founder of the Monastery. However, Delouis points out that such a person is not known from any historical source.

The earliest mention of the Monastery is in a document of 1018/9 concerning the resolution of a border dispute between the three neighbouring monasteries of Great Lavra, Amalfinon and Karakallos. A few years later, however, in 1045, the Karakallos Monastery is curiously absent from the list of monasteries whose representatives signed the second charter of Mt Athos, which was prepared during the reign of the Emperor Constantine III Monomachus. This absence, which is difficult to interpret, is added to the question that we already have about the exact time and conditions of the Monastery's founding, as well as about the identity of its founder or founders. As for the meaning of the name, there are only legends and speculations. As Olivier Delouis notes, throughout the medieval period the Monastery is referred to as Karakàlou, Karakàllou, Karakàlous, Karàkala or Karakalà. So, the founder may have been named Karàkalos, or Karàkallos, or Karakàlas, or Karakalàs, or someone with a completely different name.