This article discusses the deductibility of payments made to extinguish a liability under Australian Taxation Law. It examines Section 40-880 of the Income Tax Assessment Act, 1997, Taxation Ruling TR 96/23, and landmark cases such as Sun Newspapers Ltd v FCT, Californian Copper Syndicate v. Harris, and Myer Emporium v. Federal Commissioner of Taxation. The article concludes that if the expenditure incurred by the taxpayer was for producing an asset or advantage of a lasting nature, it would be considered as capital expenditure. However, voluntary payments made under no obligation and without any expectation of return or benefit are not deductible.