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Surplus stripping has been the most frequent issue of application of the General Anti-Skimming Rule since its inception in 1988. Whether it is the circumvention of specific anti-stripping rules such as section 84.1 and subsection 84(2) of the Income Tax Act; the artificial transfer or creation of tax attributes; the use of a trust or partnership; and the abuse of attribution rules or tax treaties; Surplus stripping generally involves the ultimate distribution of corporate profits to individuals, in any manner other than through taxable dividends, by circumventing or using, often abusively, the provisions of the Income Tax Act.This essay discusses the intent of the legislator and maps out acceptable, uncertain or abusive planning vis-à-vis the GAAR. Case law, technical interpretations, legislative amendments and proposals, and doctrine have been helpful in this exercise.