This thesis deals with the problem of how to understand and explain strategic surprise in relation to the crisis in Ukraine 2013-2014. It describes the events that triggered surprise and identifies the EU Vilnius Summit, the Maidan square massacre and the annexation of Crimea as focus points. Using a theoretical framework based on surprise theory, the thesis examines the agenda of the EU Eastern Partnership, the psychology of Foreign Ministers Carl Bildt and Radek Sikorski before the identified focus points, and the organizational dynamics of the European Council throughout the crisis. The conclusion is that the Eastern Partnership agenda provided a toolbox with limited usability in a crisis, that the overconfidence of Bildt and Sikorski meant they failed in turning registered warning signs into a rethinking of policy, and that procrastination by the European Council led to a reactionary pattern that contributed to recurring surprises.