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This thesis examines military decision-making under uncertainty in the context of hybrid threats and counterintelligence operations conducted by the Swedish Armed Forces. The study analyses how uncertainty, agility and legitimacy interact in decision-making processes to enable initiative. Empirical data were collected through field observations and focus group interviews and analysed through reflexive thematic analysis, guided by a theoretical framework based on Boyd’s OODA-loop. Findings indicate that military commanders seek to exercise agility under conditions of legal ambiguity, time pressure and potential risks to organisational reputation. Organisational agility and the prevailing culture are not perceived to promote or reward initiative. Initiative and individual agility can be enhanced when acceptance of uncertainty is seen as inherent to decision-making and when legal conditions are understood as enablers rather than obstacles. The study contributes an empirically grounded theoretical framework for decision-making under uncertainty and advances understanding of military decision-making in complex operational environments.