The interpretation of South Africa's general anti-avoidance rule (GAAR) by the courts has been influenced by the Duke of Westminster principle. This principle was restated in the 1999 decision of the Supreme Court of Appeal in Conhage (Pty) Limited, which to a great degree emasculated the existing GAAR. In November 2005, the South African Revenue Service issued a Discussion Paper on tax avoidance dealing with the problems experienced with tax avoidance generally and setting out the reasons for the new legislation to be enacted as a new substitute GAAR. This article provides a brief history of South Africa's GAAR which led to the proposed change. The article also points out the salient features of the Discussion Paper.