Liberal democracies have struggled recently with protecting freedom of speech and assembly during the COVID-19 pandemic. This is an old, general problem in new, specific guise. In Australia, the Supreme Court of New South Wales has been exercising a statutory jurisdiction to ‘authorise’ or ‘prohibit’ proposed public assemblies for 40 years. This article offers the first sustained analysis of the Court’s jurisprudence. After describing the operation of the statutory permit scheme and systematising the case law, this article critiques the Court’s jurisprudence from the perspective of free speech and freedom of assembly. It then argues that there is a puzzle at the heart of the legislative scheme: the conferral of a wide discretion the exercise of which produces a narrow legal order. This puzzle suggests that the legal effect of an authorising or prohibiting order does not exhaust its broader social significance.