With much of the global political momentum shifting towards greater fragmentation and uncertainty, closer cooperation between the EU and the Association of South- east Asian Nations (ASEAN) is not just beneficial—it is strategic. As stabilisers amid uncertainty, by working together during unpredictable times, the EU and ASEAN can project predictability based on a shared commitment to a rules-based order. Faced with a less-reliable America, an aggressive Russia and an assertive China, Europe is stepping up to boost resilience and carve its own way forward. Notwithstanding regional diversity, the ASEAN countries are working on lessening their reliance on major powers and seeking to foster greater intraregional integration in trade and digital connectivity. This policy brief explores the dynamics in EU–ASEAN relations amid the current global uncertainty, and urges the adoption of a flexible and pragmatic strategy to maximise potential and project power. The EU and ASEAN must work from the bottom up and develop strategic maturity to accommodate each other’s differences in worldviews and perceptions. The present moment offers an opportunity for the middle powers to exercise greater agency and help to shape what comes next for geopolitics and technology.