The evolution of Online Dispute Resolution (ODR) as an augmentation from Alternative Dispute Resolution (ADR) may lead to an authentic paradigm shift in the way disputes are handled beyond the traditional court systems. To assess state of the art and convey awareness, this paper explores the regulatory landscape of the European Union (EU) using the United Kingdom and Estonia to illustrate the key advancements and shortcomings of the supranational strategy. It discusses the relationships between ADR capabilities and its productive use in ODR, the ODR deployment and adoption, and the consequences that may arise if dispute resolution technologies leapfrog. The paper also speaks of automation and suggests the need to build integrative models into Artificial Intelligence (AI) - powered ODR platforms. It is apparent that the early challenges in the development of the ADR culture in the EU are still unresolved, affecting the proper integration of ADR principles and ODR technologies. A more effective coupling could be expected to smooth digital trade interactions by increasing access to justice and consumer trust in the redress capacities of the Dispute Resolution System (DRS) as a whole.