In the present study, on the basis of a rich archive material, the author analyzes the land disputes between Moldavian monasteries and Bessarabian landowners in the first decades after annexation, based on an example of the transaction concluded by the landowners Leon and Tomuleţ with the monastery of St. Ioan Zlatoust from Iasi. The author ascertains that the transaction has in fact led to a long dispute between the parties who have concluded the exchange, which lasted until the end of the 1820s, with adverse effects both for the St. Ioan Zlatoust monastery in Iasi and Tomuleţ and Leon landowners, as well as for the inhabitants of Lăpuşna, especially for those who lived in the hearth of the former fair, which at the beginning of the 19th century fell to a state of a village, as well as for some people who risked, due to the dispute between the two parties, to lease the estate’s income, etc. The changes occurred in regard to the owners of the Lapusna estate practically did not solve the dispute with the inhabitants, but even aggravated it, advancing from disputes in the courts of law, to direct confrontation, which led some scholars to believe that these events preceded with a decade the similar processes that carried out in Moldova in 1831.