This article examines the eventful history of the bailiwick of the Benedictine monastery of Remse near Glauchau, founded in the middle of the 12th century. Close to the empire and under royal protection in the High Middle Ages, with the collapse of the Hohenstaufen kingship first the lords of Waldenburg and then, as their heirs, the lords of Schönburg took over the bailiwick of the nunnery. In the 15th century, the convent, together with the mother monastery of Bürgel, tried to escape the bailiwick of the Schönburgs and instead place itself under the patronage of the Wettin hegemons. An extremely favourable situation in terms of tradition provides detailed insights into the preparation and implementation of the legal disputes from the 1480s onwards, in which even the falsification of documents was not shied away from, for the purpose of “de-bailiwicking”. The monastery did succeed in replacing the lords of Schönburg as monastery bailiffs, but at an economically ruinous price. At the same time, general transformation processes of the late Middle Ages can be shown within the framework of a micro-historical study, such as the establishment of a closed sovereignty of the Wettins by eliminating the special rights of smaller lords.