When the Court of Appeal rendered the decision of Tan Kiam Peng in 2008, it was unable to come to a conclusive determination of the correct interpretation of s. 18(2) of the Misuse of Drugs Act, a provision pertaining to the presumption of an accused’s knowledge of the nature of the controlled drugs in his possession. This issue was presented to a differently constituted Court of Appeal in Nagaenthran, which seemingly ruled in favour of the narrow interpretation of s. 18(2) as opposed to the broader interpretation. Nagaenthran, however, did not address the questions raised by Tan Kiam Peng vis-à-vis s. 18(2) in a comprehensive fashion. Indeed, there are various angles in which light can be shed on the prism that is s. 18(2), and in this paper, three separate and distinct heads will be considered, paying particular regard to cases and perspectives that could have impacted Nagaenthran, but were not discussed or elaborated therein: (a) whether there is a practical difference between the two interpretations; (b) what more can be said about the purposive interpretation of s. 18(2) undertaken in Tan Kiam Peng and other interpretive issues that may arise for consideration; (c) whether cases from Hong Kong, which has legislation similar to s.18 of the MDA, can offer assistance.