ENThe article is devoted to the mechanisms of the formation of the border between the Duchy of Courland and Semigallia and the Grand Duchy of Lithuania in the second half of the 16th century. Delimitation of the border between these socio-historical organisms was based on the old contracts from the period of the Livonian Order. The lack of an actual demarcation line right up until the moment of the emergence of the Duchy of Courland in 1561 resulted in a number of highly varied privately fought disagreements. This said, the southern borders of Courland, established by the end of the 16th century, are largely preserved to this day in the form of boundaries between modern Latvia, Lithuania and partially Belarus.