Statistics South Africa indicates that in the third quarter of 2015 the rate of unemployment in South Africa increased to 26%. Joblessness has always been a post-1994 conundrum, exacerbated by the unstable global economy. Because of this, various economic means are pursued to sustain livelihoods. Among these is informal street vending - tinkering at the periphery of the mainstream economy. This article examines this economic activity, which in 1991, was deregulated. The contextual setting of the subject of the article is Polokwane - one of the largest urban areas in the northern part of South Africa. The question that is asked is: What is the implication of deregulating the street vending industry on the environmental conditions of cities and towns in South Africa? An attempt to provide an answer draws from the research the author conducted to understand the challenges facing informal street vendors. The article is biased towards str