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This dissertation examines immigration and citizenship policymaking in Canada and Germany, focussing on the expansion of both states' membership regimes after World War II. Canada and Germany's initial solutions to the migration-membership dilemma were developed in the early-twentieth century and included policies that prohibited the entry and incorporation of groups deemed undesirable because of their putative racial or ethno-national characteristics. Canada implemented policies and administrative practices that barred non-white immigrants, while Germany combined a system of temporary foreign worker recruitment with a descent-based citizenship law that excluded unwanted groups and reinforced an ethno-cultural conception of German national identity. I argue that world-historical events and epoch-defining processes, including the Holocaust, decolonization, and the emergence of a global human rights culture, created a markedly different normative context in the postwar period that discredited principles used to legitimize prior exclusions, creating a lack of fit between Canada and Germany's postwar commitments to liberal-democratic principles and human rights, on the one hand, and their extant immigration and citizenship policies, on the other. Domestic and international critics highlighted these inconsistencies and pressed for reforms, obliging policymakers in Canada and Germany to stretch policies to conceal incongruities produced by this lack of fit. Policy stretching failed to mollify critics and further undermined the intellectual coherence of established frameworks, hastening their unravelling and opening space for the formulation of new approaches. In Canada, policy stretching, unravelling, and shifting culminated in the introduction of a universal admissions policy based on the so-called points system. In Germany, failure to implement an effective mechanism for ensuring the rotation of temporary foreign workers allowed for de facto immigration, which, in time, necessitated further reforms in citizenship policy to incorporate settled migrants and their families. Through detailed case studies, I demonstrate how differences in domestic political institutions and processes affected the course of unravelling and policy shifting in the two countries, leading to variation in the timing and extent of change. Political factors facilitated the introduction and entrenchment of new solutions to the migration-membership dilemma in Canada, while delaying and limiting the scope of policy shifting in Germany.