Border and administrative divisions usually have considerable severe impacts on the economic growth and sustainable management of natural and human on both sides of the border. Schengen border regions mostly perform less well economically in comparison to non-border regions, and the citizens and businesses are facing all sorts of barriers on a day-to-day basis when crossing EU Schengen borders. Therefore, the research is focused on the resilience of the frontier areas of Slovakia and Ukraine, both experiencing rising out-migration, demographic ageing and, therefore, less resistance to threats. The proposed Regional Resilience Index (RRI) is based on three resilience capacity domains: (1) The entrepreneurial domain containing partial indicators of industrial diversity, entrepreneurial activity, unemployment and the possibilities to save money; (2) the socio-demographic domain, whose partial indicators are ageing and the health status of the population, and (3) the domain of interconnectedness of communities with its partial indicators of public infrastructure and settlement stability. By calculating RRI, the overall resilience capacity of the monitored districts of Slovakia and Ukraine is estimated. The index shows that the border factor is significant in explaining the differences in each of the index’s three domains. In addition, migration for work is shown to be a key factor increasing vulnerability and is therefore studied in more detail. The prediction and evaluation of risks associated with strategic and territorial planning is a necessary approach in relation to extraordinary events and minimization of consequences.