The fact that we know the end points of formal colonial rule may lead us to forget that, for those involved, the process appeared less determined and more contingent. It is deceptively easy to trip over the supposed ‘milestone’ of the Second World War, ascribing undue influence to a failing capacity or will to rule among the colonial powers themselves. Such generalizations leave no room for agency among colonized peoples themselves and dismiss both rulers and ruled as essentially homogenous, almost preprogrammed to behave stereotypically as reactionaries or revolutionaries. Recognizing these interpretive problems, political analysts of European decolonization are now more divided over the extent to which the Second World War prefigured the end of European colonial rule. Much of the evidence for a strong causal link is powerful. By 1950 the geopolitical maps of eastern, southern, and western Asia were markedly less colonial. The justificatory language for empire was also different, evidence of the turn towards a technocratic administrative style that would soon become the norm in much of the global South. If basic political rights were frequently denied within dependent territories, a stronger accent on improved living standards gave imperial powers something with which to muffle the rising chorus of transnational criticism against colonial abuses. For all that, the concept of the Second World War as a watershed in the end of empires should not be accepted uncritically. This chapter explores the reasons why.