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South Africa is a migration destination with a paradoxical policy environment. On the one hand it is generous – extending access to health care, education and rights for women, homosexuals and persons with disabilities to all persons within its borders. On the other hand, it is stingy and obstructive – tolerating a large informal labour market with uneven protections disadvantaging migrants, high hurdles for asylum seekers and one of the most extreme inequality rates in the world. As transnational workers, children, partners, spouses and parents expand their social, economic and physical footprint beyond their home countries they confront South Africa’s borders, laws and policies. They also encounter South Africa’s ongoing project to build a collective national identity and semblance of ‘social cohesion’, a project that has proven contentious, sometimes violent and arguably, poorly managed. With global migration trends increasingly South-South in orientation and largely inter and intra-regional, this article focuses on South Africa, examining the incentives and disincentives that influence family decisions to transnationalize to South Africa and how those decisions, in turn, shape and are shaped by law, policy and society.