The chapter identifies warnings within the EU foreign policy system related to the Russian annexation of Crimea and the destabilisation of Eastern Ukraine in 2014 and examines the reasons for the differentiated impact among EU decision-makers. The Ukraine case was a strategic surprise to the overwhelming majority of EU policy-makers and posed significant diagnostic problems, but senior ministers within the system were warning their peers on the basis of previous cases, historical analogies, expert knowledge and recent indications of changed Russian intent. However, the persuasiveness of the few and late warnings suffered, first of all, from distraction by external crises coupled with limited bandwidth in the EU, shortages in relevant and reliable intelligence, high resistance against divergent policy predispositions of the warning and, finally, significant suspicions of national biases against key warning sources. The supranational part of the system was almost completely blindsided to geopolitical risk, while the newly established EEAS was partly unable and partly unwilling to persuade the Commission. It is fair to say that the system as a whole acted as an impediment to having a holistic discussion of warning as part of foreign policy discourse.