The presumption of advancement has been subject to criticisms by the Singapore courts. Judicial attempts have been made to marginalise and relegate it to an evidentiary rule of last resort which is easily rebuttable. However, the latest Court of Appeal decision, which reaffirms its usefulness, appears to have resuscitated the presumption in Singapore. This article—subjecting the Singapore cases to comparative developments in other jurisdictions—seeks to advance a proper understanding of the underlying rationales of the presumption, clarify its function, and propose suggestions for its more consistent application.