An integral part of the implementation of any reform is the emergence of the risks of its negative impact on one or another area of region development. The decentralization reform in Ukraine is not an exception. In its the context the most probable occurrence of negative phenomena is in the border regions, which could be prevented by first detecting them. In the scientific article, the authors focus on the analysis of a number of challenges for the development of border regions in the context of decentralization reform. Given the territorial remoteness of the central regions of the country and the capital, which today serve as areas of concentration of investment and economic activity, the border regions traditionally (this is typical for the border areas of the EU member states) lag behind the rest of the regions by the main socio-economic indicators of development. Among the main challenges facing the border regions of Ukraine today are the following: the provision of competitiveness in the context of European integration processes and reduction of the border barrier function; low level of economic security; the outflow of human capital and the issue of ethnic minorities. Based on an expert survey of representatives of the fifteen united territorial communities (UTCs), the possibility of such risks of decentralization in the border regions were defined as following: groundless use of local budget funds; emergence of significant imbalances between delegated new authority and available financial resources of the community; increasing uneven development of territories within the community; increasing uneven development of communities within the country; deterioration of the availability and quality of providing educational and medical services; deterioration of the quality of local government; reducing of the state influence on the management of local development processes; radicalization of political unions representing the interests of ethnic minorities in places of their compact residence; further economic decline of the territory of communities and so on.