The experience of European small states involved in World War II varied widely. Not all of them entered the war as victims of aggression, and even those that did so did not necessarily share the same dire consequences of warfare and/or foreign occupation; they also exited the war in, sometimes dramatically different ways: a number of small states entered the post-war period relatively peacefully, other were plunged into civil war, while a third category experienced a measure of unrest short of civil strife. It is argued in this paper that, among the factors influencing the outcome of a European small state’s involvement in World War II, the political legitimacy of its government should not be underestimated. The impact of this factor was particularly felt during the sensitive transition period from war and/or occupation into peacetime. Reinterpreting existing material, it is further argued that, during the war, democratic legitimacy increasingly appeared to guarantee a safer ground for both withstanding wartime travails and achieving a relatively smooth restoration of free national institutions, without the risk of civil war.