This article reviews some of the recent challenges to the legal status of homosexuality in Singapore. On July 14, 2014, the Court of Appeal of Singapore heard oral arguments from two sets of plaintiffs regarding the repeal of Section
377A of the Singaporean Penal Code: the section of the code that criminalizes gay male sex between two consulting adults. This article demonstrates how the cases on appeal uncover a trepidatious government carefully untangling itself from values left behind by Colonial rule, and an equally apprehensive court system that seeks refuge in outmoded statutory guidelines and shifting popular sentiment. The article also aims to document some of the changes over the past few decades in Singapore’s landscape that have contributed to the monumental changes taking
place regarding gay rights in the city-state, and how such changes may hopefully provide for the broadening of civil rights and the easing of governmental control in the near future.