ENThe article concerns a difficult art of administering a non-city Wobolniki county (starostwo) in Troki province, Upicki poviat, by Jan Karp, a Samogitian Cześnik (Cup-Bearer). The study has been based on Karp’s correspondence addressed to Duke Karol Stanislaw Radziwiłł, Grand Chancellor of Lithuania from January 1708 to March 1709. The author focuses on Karp’s problems with the county administration and insistent attempts to fulfill his obligations towards Radziwiłł, such as paying rent and collecting taxes. Karp’s problems resulted, most of all, from the warfare conducted within this territory, which entailed war contributions and seizures imposed by the raiding Swedish troops. Moreover, the problems were caused by exterminatory raids by Moscow and Lithuanian armies that were reduced to plunder and arson. In conclusion, the author writes about general impoverishment of the county population as a consequence of the warfare, which was additionally decimated by outbursts of bubonic plague.