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While the South African and Australian general anti-avoidance rules ('GAARs') differ in their structure and design, each is directed towards the same end. Although the South African GAAR was substantially amended in 2006 to address perceived inadequacies, there has yet to be any judicial consideration of the 'new' provision. While it is a highly prescriptive provision (at least in comparison with its Australian counterpart) considerable uncertainty as to its effectiveness remains, especially as an earlier attempt to remedy many of the same deficiencies in 1996 was spectacularly unsuccessful.Meanwhile, after a slow start, the jurisprudence on the Australian 1981 GAAR continues to gather momentum. Although many of the application and interpretative issues have gradually been resolved, others seem insoluble.In this paper the authors examine these two GAARs with a view to identifying if any lessons for their application and interpretation can be gathered from each other. The authors argue that, notwithstanding design differences, there are some remarkably similar issues to be resolved. Some of the Australian case law may therefore be instructive as to the approach that could be adopted in South Africa, while some of the prescriptions in the South African legislation could be of value in assisting the Australian judiciary to direct their attention to relevant considerations or, possibly more likely, could form the basis for further legislative prescriptions in the Australian GAAR.