There is an ongoing debate regarding whether the EU-10 converges at the core of Europe or not. Although the evidence supports both perspectives, the gap in urbanization is undeniable. In this explorative study, two economic processes contributing to this disparity—foreign direct investment and migration—were analyzed and contextualized with respect to urbanization using grounded theory. It was concluded that there is slight convergence in the frontier, usually in urbanized areas of Central and Eastern Europe (CEE), but not in the rural areas; additionally, the rural–urban dichotomy within the CEE countries is deepening due to the self-enhancing nature of the analyzed processes.