The English language has been present in South Africa since the end of the eighteenth century. Although regional varieties were established as part of the nineteenth-century development of South African English (SAfE) as its own variety, the general consensus has been that since the mid-twentieth century the ancestral ‘settler’ variety of SAfE has shown a high degree of regional homogeneity and only a limited set of regionalisms. This chapter investigates more recent developments in this regard, drawing on an acoustic analysis of data from upper-middle class male and female speakers of General SAfE from the three largest urban conurbations of South Africa: Johannesburg, Cape Town and Durban. The focus is on vowel quality and the results include (1) greater centralization of KIN in Durban (2) a Cape Town-centered process of TRAP and DRESS lowering accompanied by STRUT backing (the so-called Reverse Short Front Vowel Shift in SAfE) (3) clearly diphthongal variants of PRICE in Johannesburg and Cape Town in comparison to Durban and (4) backed and lowered variants of GOAT in Johannesburg and Durban as compared to Cape Town. Overall the results suggest a growing degree of regional differentiation in South African English.