Through a multi-method qualitative case study, I examine the failed 2016 ballot campaign of the Committee for Professional Policing (CfPP), a police accountability group in Minneapolis, Minnesota. In attempting to make Minneapolis the first city nationwide to require police to carry professional liability insurance, the CfPP turned the logic of Malcolm M. Feeley and Jonathan Simon’s “new penology” paradigm onto police. Their thesis argues that a contemporary penal shift occurred away from rehabilitation toward managing aggregates of dangerous criminal categories through risk management approaches. I extend their thesis in a new direction by examining how—in the emerging age of “algorithmic risk governance”—social movement organizations, like the CfPP, are starting to invert the new penology onto criminal justice personnel. In flipping the script, the CfPP called for a new private insurance market using mandatory police misconduct insurance to manage aggregates of dangerous police officers. After highlighting how the CfPP developed new penological objectives, discourses, and technologies, I discuss the implications of grassroots groups adopting and redefining traditional penal logics and propose future research avenues.