The polysemy of crisis anticipation and decision-making in crisis situations, and the difficulties regularly encountered during these processes, have been highlighted in the literature. This paper illustrates the obstacles to accurately predicting crisis situations by demonstrating the fragmentation of the pair anticipation/decision-making. It does so through two studies involving the Caribbean Irma–Jose–Maria hurricane sequence (2017), through the respective lenses of the French National Crisis Coordination Centre at the Interministerial level and of a government operator, the French Geological Survey, at the territorial level. Absence of shared vision within and between crisis management rooms regarding the nature, time horizon, and methodological framework of the anticipation function all hampered its effective implementation during the hurricane sequences. This was mainly due to the coexistence of different ministerial cultures regarding crisis anticipation and the siloed structure of the French Crisis Management System. Findings suggest that time is a critical structuring element for adaptive and shared anticipatory approaches. Therefore, the anticipation/decision-making pair can be seen as a continuum integrating all temporalities from prevention to crisis management and reconstruction. This new paradigm should be applied through the plurality of administrative cultures, which are in great tension with each other in preventing and managing crisis situations.