This paper examines the intersection between immigrant incorporation regimes and the legacies of postcolonial migration practices in order to explain outcomes of contemporary minority political and social integration in Europe. Rather than treating the outcome of integration as the linear byproduct of incorporation regime structures, I also consider migrants’ ability to “invest” in their own integration into the host country as a key determinant, namely in the form of citizenship, language acquisition, cultural familiarity, and the network benefits of large numbers of co-migrants. This article explores the extent to which postcolonial migrants have an investment advantage over non-colonial immigrants, and how this translates across generations. Using extensive data from Maghrebi and Portuguese immigration in France, I find support for the theory that postcolonial legacies have historically eased the very initial transition for first-generation migrants; However, the reverse is true for subsequent generations of immigrants. I find that in French context, in which the immigration regime discourages transnational loyalties and communitarianism in favor of adopting the national identity, the children of postcolonial migrants will actually pay an integration penalty compared to those without a colonial legacy because of their parents’ maintenance of a transnational identity.