This chapter provides a comparative analysis of when, how, and why rural-urban labor migration patterns in colonial Belgian Congo and Southern Rhodesia shifted in character from largely temporary to more permanent settlement in urban areas. We argue that differences in urban labor stabilization patterns in these two colonies resulted from complex, interlinking factors under two broader categories: geopolitical conditions and colonial institutions. Specific geopolitical circumstances affected the timing and character of each colony’s industrial take-off and the degree of integration with surrounding territories, impacting upon their respective urban labor markets and migratory flows. Meanwhile, the different contexts of the semi-autonomous settler colony of Southern Rhodesia relative to the more metropolitan-controlled Belgian Congo influenced colonial institutions and social policies with implications for rural and urban opportunity structures. This, in turn, diversely affected the decision-making of African migrants.