Europe has experienced not one, but two profound turning points within a remarkably short period of time. The first Zeitenwende began on 24 February 2022 with Russia’s full-scale invasion of Ukraine. The second followed in early 2025 with the return of Donald Trump to the White House. Together, these two moments have produced a qualitatively new condition for Europe – one defined not only by uncertainty, but by insecurity in the most literal sense. This roundtable takes these two Zeitenwenden as its starting point and focuses on a central aspect of the broader research project on German–Polish relations: the shifting roles of Germany and Poland in Europe’s security order under conditions of compounded crisis. While the first Zeitenwende shattered long-standing assumptions about peace, interdependence and Russia, the second has called into question the reliability of the transatlantic framework on which European security has rested for decades. In 2022, Germany proclaimed a historic rupture in its foreign and security policy. Yet three years later, the balance between rhetoric and action remains contested. The second Zeitenwende has intensified this tension. Signals of a growing American disengagement from European security and Washington’s transactional approach to alliances have exposed Europe’s strategic vulnerabilities with unprecedented clarity. In Poland, these developments carry a different meaning. The war in Ukraine confirmed long-standing threat perceptions and validated years of warnings about the Russian threat directed at Berlin and other Western capitals. Poland’s growing military capabilities, its outspoken stance on Russia and willingness to assume risks have elevated its visibility in European security debates. At the same time, the new uncertainty raises uncomfortable questions: Is Poland becoming a security actor by necessity or choice? Can its assertiveness translate into sustainable leadership without broader European backing? The roundtable explores how the interaction of these two Zeitenwenden has altered German–Polish relations. It tries to answer whether the traditional “teacher–student” dynamic is eroding under pressure, or whether old hierarchies persist because Europe lacks clear leadership. How do Germany and Poland interpret each other’s roles in an environment where neither certainty nor security can be taken for granted? How does Europe’s apparent inability to act decisively deepen both uncertainty and vulnerability (insecurity)? The discussion will conclude by asking what forms of German–Polish and regional cooperation might help Europe overcome its current strategic impasse under conditions of transatlantic unpredictability. Designed as a moderated, policy-oriented conversation, the roundtable invites participants to reflect on how Central and Eastern Europe is navigating an era shaped by a dual rupture, and on whether these moments of radical uncertainty can still be turned into catalysts for strategic clarity.