This article considers the origin, development, change in the status, and extinction of enclave and exclave formations in the territory of the modern Kaliningrad region. The author offers information on their socio-economic and political features. The article identifies enclave (exclave) problems peculiar to them, including the land access (passenger and cargo transit) of the metropolis to the isolated territory, as well as the issues relating to the origins of state border, border control, visa regime, and political and economic relations to neighbouring states and the mainland. The author reviews cases of evolutional development of enclavity and peaceful and military methods of eliminating enclave formations. Actions towards the solution of political and socioeconomic problems taken in East Prussia are compared to those taken in the Kaliningrad region. The author emphasizes the need to solve the problems of the only Russian exclave region in view of the experience of its historical “predecessors”.