This chapter’s intention is to present and analyse urban border locations, and the various geopolitical and/or economic reasons for their situation, based on examples from different periods of the Prussian-German territories, from 1701  to 1989. The area formed a conglomerate of territories, changing in spatial configuration. Almost by chance, some of Prussia’s and Germany’s towns came to be situated on, or very near, the boundary with another, often hostile, state. In some cases, these towns had a trans-border twin; in others, a twin town was intentionally built as a result of a new border delineation. The chapter will highlight four cases: Anklam, an 18th century border town with a split administration, Tilsit/Sovietsk under extreme geopolitical changes, The Free City of Danzig and its new Polish border replica, Gdynia, and the river towns separated by the Oder-Neisse agreement.