The ‘right to the city’ is a right of the city’s denizens to have a say in shaping and using their urban environment. Recognizing the city as the locus of technological development and innovation, scholars have also begun theorizing about a ‘digital right to the city’, the right of citizens to play an active role in managing the way they create and control the information relating to how they experience and use the city. Against this backdrop, this chapter considers two aspects of Singapore law—the Public Order Act (Cap 257A, 2012 Rev Ed) and the Protection from Online Falsehoods and Manipulation Act 2019 (No 18 of 2019)—that impinge upon the (digital) right to the city, and the more traditional constitutional rights to free speech and assembly. It seeks to assess the extent to which these civil liberties might impact upon the way the laws are interpreted and applied, and also considers whether there are ways in which aspects of the laws might be reimagined to give better effect to the right to the city in both its forms.