The ‘Operation Iraqi Freedom’ in 2003 raised many international legal questions, which all have been more or less addressed in the academic literature since then. However, the thrust of the relevant legal etiology pertained to the implementation of a series of UN Security Council Resolutions, whose hermeneutics, ie the rules of interpretation, in contrast to other issues, have been scarcely explored and elucidated. Accordingly, the purpose of this article is to address the latter question of the hermeneutics of Security Council Resolutions, and propound a coherent thesis in this respect, which would be applicable not only in the Iraqi conflict but even beyond. It will examine, first, whether the provisions of Articles 31–33 of VCLT are applicable either ipso jure or mutatis mutandis in this respect and then having deprecated both of these options, it will turn its focus to the question of which theoretical framework in relation to the hermeneutics in international law could better serve its purposes. Drawing insights from, amongst others, Stanley Fish, Ian Johnstone and Aharon Barak, it will be possible to propound the thesis that any relevant regulatio interpretations should pay due regard to the institutional setting of the ‘community’ of the Council, which in turn qualifies the ‘inter-subjective’ approach or the collective will of the Council in light of the object and purpose of the Charter, ie the maintenance of peace and security, as the most pertinent hermeneutic paradigm. Premised upon the latter, the article proceeds and articulates a rubric of interpretive principles and presumptions to be applied in this regard, which, at the end, will be tested in the case of ‘Operation Iraqi Freedom’.