The accession of the East-Central European (ECE) countries carried a promise of enhancing and enriching the EU’s Eastern policy. The new member states had the strongest interests among EU member states to ensure that countries in the East are prosperous, stable, and democratic. Yet, the EU’s Eastern policy has been largely criticised for its ineffectiveness. So why have they not been able to address the shortcomings in the EU’s Eastern policies? The article argues that the ECE countries supported the way the EU’s Eastern policies were conceived and implemented because they saw it as a potent vehicle to promote their own transition experience not only in the region but also within the EU. We argue that the ECE states have experienced three types of challenges when promoting their transition experience. First, uploading to the EU level remained largely at a rhetorical level. Second, there are conceptual and practical difficulties in defining what constitutes transition experience and harnessing it, as well as coordinating its transfer between the ECE states. Finally, while using transition experience as the basis for their development assistance strategies, the ECE countries actually insufficiently conceptualised the "development" aspect in these policies. Being so driven by their own experience, they have not drawn the lessons from enlargement to use in a non-accession context, especially by incorporating the broader lessons with regard to development.