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 Colon