This paper proposes that the traditional theoretical-methodological approaches that have analyzed the relationship between city and immigration are necessary, but also insufficient to capture three contemporary dynamics: the interconnected global processes of socio-spatial segregation; the destabilization of geo-historical categories such as “North”- “South”; and, the specific historical geography that has occurred in Latin America as a result of the intensification of certain migratory processes. Strategically focusing on the residential relocation of North American retirees in Latin America during the twenty-first century, this paper proposes that some small and peripheral cities in the region have become spaces in which, based on structural dynamics of accumulation and dispossession, geographically dispersed populations have converged and multi-scalar processes of inequality have been configured. It is posited that the residential relocation of North American retirees is symptomatic of a novel form of externalization of the U.S. border that operates differentially when migratory flows go from “North” to “South” or from “South” to “North”. This border externalization is expressed in the extraterritorial expulsion of a U.S. population considered, to a certain extent, surplus, but it also manifests itself through fractal recursions of the border—a multi-scale structure that reproduces renewed antagonisms in different dimensions—that permeate spatial, symbolic and intersubjective relations in the receiving Latin American cities.