This chapter examines Cruiskeen Lawn during the period of the Second World War (the “Emergency” in Ireland) with a focus on how Myles na gCopaleen navigated censorship, neutrality, and wartime anxiety. Against claims that wartime columns were evasive or politically inert, the chapter argues that O’Nolan developed a sophisticated “aesthetics of the half-said,” allowing him to comment incisively on international conflict and domestic policy while remaining within the constraints of the Emergency Powers Act. After outlining Ireland’s political and cultural climate—marked by neutrality, press censorship, shortages, and heightened state control—the chapter analyses how Myles employed allegory, parody, mock bureaucracy, and linguistic play to smuggle political critique into the public sphere. Particular attention is paid to representations of neutrality, rationing, censorship, and the general elections of 1943 and 1944, as well as to Myles’s oblique engagement with fascism, British policy, and the moral ambiguities of Irish non-belligerence. The chapter situates these strategies within O’Nolan’s personal and professional circumstances as a civil servant and journalist and argues that the Emergency constituted a turning point in his career. Ultimately, the chapter contends that Cruiskeen Lawn offered a subtle yet informed critique of wartime Ireland insofar as it functioned as a politically alert form of satire rather than a retreat into solipsistic humour.