For decades, drug trafficking was a serious offence in Singapore potentially punishable by mandatory death. In 2012, Singapore’s Misuse of Drugs Act (MDA) was amended to give the courts sentencing discretion if the accused can first prove that he was merely a courier, and to better reflect the moral culpability accorded as between mules and kingpins in the hierarchy of drug syndicates. However, there are some complications in proving this. Not only must the accused show that he was merely a courier, he must also show that he had substantively assisted the authorities in disrupting drugtrafficking activities in Singapore. This raises an evidential quagmire as it is for the prosecution to certify that such assistance had indeed been rendered – the accused is therefore incentivised to admit to some form of guilt from the outset rather than to remain silent, since he may be precluded from adducing evidence of his role as a courier once the judge is satisfied that a drug-trafficking charge has been made out. Questions of self-incrimination and presumption of innocence are thus engaged. In addition, it is questionable if prosecutorial discretion should be further fortified by placing the certification power in the hands of the prosecutor. Finally, the MDA only states the preconditions of when there may be a discretionary death penalty, but does not state under what circumstances it should be preferred. Part 1 of this article establishes the background to Singapore’s historical approach towards drug-trafficking. Part 2 provides a synopsis of the first major High Court decision that addressed the amended MDA provision, while Part 3 analyses the decision as well as related case law. Concluding observations reside in Part 4.