In this article we discuss how transnational motherhood is managed and experienced in contexts of uncertainty and conflicting pressures. We propose a conceptual approach and apply it to a specific case: female migration from Cape Verde to Europe and North America. The analysis is based on extensive ethnographic fieldwork conducted by the authors in Cape Verde and the diaspora over the past decade. We first address the ideal of and expectations towards transnational mothering in Cape Verde, relating these to local forms of kinship, fostering and household organisation. We demonstrate that lengthy separations between mothers and young children are socially constructed as a normal aspect of transnational lives: they are a painful necessity, but are not automatically assumed to be traumatic. In an ideal situation, the biological mother and the foster mother play complementary roles in what we describe as the transnational fostering triangle. Subsequently, we ask how transnational mothering is confronted by unforeseen incidents and obstacles, which we refer to as contingencies. We relate these contingencies to the negotiation of individual and collective ideas and aspirations. The Cape Verdean case is interesting in a comparative perspective because of the social acceptance of mother–child separation. Our analysis explores how this acceptance co-exists with the real-life challenges of transnational mothering.