Using interview data from protesters and frontline police, this chapter examines the transition of protest policing, from soft to hard models, amid the recent unrest in Hong Kong. While police-centric explanations in the protest policing literature view police as intentional decision-makers who can choose from a variety of policing strategies, we employ a mixed-embeddedness framework that reveals a number of factors—external to police—that have deprived the Hong Kong Police Force of its capacity to facilitate peaceful protest through soft strategies of communication and negotiation. These include, (1) a legitimacy crisis of governance in Hong Kong (a macrolevel factor), (2) the erosion of police authority within the local political culture (a mesolevel factor), and (3) stylistic changes in police–protester interactions, involving the increased use of masks and collective action frames of identification as victims of police (microlevel factors). Together, these factors inaugurated reaction spirals that led to the end of soft, facilitative protest-policing in Hong Kong.