This article examines the historical as well as contemporary significance of South Africa’s 1913 ban on the recruitment of migrant workers from areas north of latitude 22 degrees south. This ill-conceived policy not only criminalized the employment of so-called “tropical natives” in South Africa but also triggered contestations, fueling illegal migration from the restricted areas. By 1933, when the ban was lifted, illegal migration from Zimbabwe (then Southern Rhodesia) had become a major site of contestations among policymakers, labor agents, business owners, and migrant workers in South Africa. While the dominant narrative in Southern Africa holds that illegal migration only became an issue of concern after the end of apartheid rule, this phenomenon has a much longer history in the subregion. Identifying factors that push people to move from one country to another and those that force or encourage travelers to cross international boundaries without following official channels facilitates the understanding of the complexities involved in cases of illegal migration wherever this practice exists. While low wages and other sources of insecurity in colonial Zimbabwe may indeed have compelled many people to consider moving to South Africa, such factors did not cause migrants to use unofficial channels in crossing the border. Rather, South Africa’s ban imposed numerous barriers, rendering it difficult for those seeking work to cross between the two countries through legal and/or formal channels.