A central argument of this article is that the exercise of police power in respect of protests is relatively autonomous of judicial pronouncements affirming or upholding rights of free speech and peaceful public assembly. Using mostly Australian examples, but also drawing on UK material and some American references, the article shows how protests have gone ahead regardless of prohibitions on mass gatherings during the COVID-19 pandemic. In New South Wales, courts have sometimes allowed protests to proceed when public health experts have assessed the risk to community transmission of coronavirus to be sufficiently low. Notwithstanding that, as they did prior to the pandemic, police have moved to prevent protests and repress protestors. Accordingly, the article takes issue with the ‘negotiated management’ model of protest policing, which perpetuates a fiction of police-protestor cooperation. Indeed, protest policing has often been conflictual and heavy-handed, even militaristic, which, paradoxically, has sometimes led to potential breaches of COVID-19-safe protocols. The article concludes by highlighting analogies between the COVID-19 crisis and the ‘war on terror’ following 9/11, including the role played by courts in attempting to limit the concentration of executive power, government overreach, and intensification of police powers under a paradigm of security.