The imperial power, Britain, was in a quandary over the extent of press freedom to allow in Nigeria, its largest black African colony, during the Second World War. This fundamental issue so emphasized by Allied propagandists as one of the freedoms for which the world was at war has not yet received scholarly attention and is investigated in this study. The colonial state so much pressurized the local press that the latter had walked a tight rope throughout the duration of the war. An anti press freedom enactment which took effect on the declaration of war had foreshadowed the muffling of freedom of expression at a critical period of Nigerian history when the press was the only viable avenue open to colonized Nigerians to ventilate war induced grievances. This historical study applies the critical evaluative methodology built on archival sources, including the newspapers in the repositories of the Nigerian National Archives, Ibadan and the University of Ibadan Library to expand the cumulative knowledge of Nigerian media history. It concludes that the Nigerian press exploited loopholes in the censorship regulations, the palpable support of the newspaper publishers for Allied victory, and the restraining influence of the Colonial Office, to articulate Nigerian grievances and evade the colonial sledge hammer. The latter situation was only reversed when the colonial state enforced full press censorship after the European phase of the war as its strategy of stemming the rising tempo of militant nationalism in wartime Nigeria. Keywords: Nigerian media history, press freedom, Second World War, British colonialism, militant nationalism