Cross border traders make a major contribution to the growth of economies in Southern Africa. Cross border trade is a source of livelihood for many poor people, especially women. However, few studies examined challenges facing cross border traders and future business prospects. The aim of this paper is to examine the challenges that face Zimbabwean cross border traders in South Africa. The paper goes further to review existing literature as well as empirical studies in order to identify the major challenges that face Zimbabwean cross border traders. Among the challenges noted are crime, harassment due to xenophobia, traders are often stigmatized as "prostitutes" or "smugglers", accommodation problems, extortion and bribery by the South African Police and municipal police officials, delays at the border post during peak periods and banks that close early and also do not operate on Sundays. The Zimbabwean Cross Border Traders Association should build office in Musina and Johannesburg so that members can easily consult with the association in times of problems and also help with marketing information like distribution of brochures showcasing Zimbabwean products sold by cross border traders and also organize fairs where Zimbabwean traders can display their products. Furthermore cases of harassment by police officials should be investigated and dealt with. Banks that do have branches at the border posts are also urged to provide 24 hour service to cross border traders.