In her work, Rossiter (2011) considered the violence inherent in representation and called for a critical social work that is committed to an unsettled practice. In following Rossiter’s call to action , this article works to unsettle the trampled ground on which I walk to draw out the unsettled nature that is critical social work within the slippery and often unknowable parameters of grassroots and professional social work spaces. In utilizing my own experience in the unsanctioned Moss Park Overdose Prevention Site and the sanctioned Toronto Safe Consumption Site, I ask, What is critical social work? How is it tied to resistance and subversion? What happens when radical roots are co-opted by the state? In three sections, Grassroots, Professional, and Positionality, I assert that social work must always be unsettled in order to resist oppressive practices within. Using harm reduction and safe consumption services to discuss an unsettled practice, I conclude that social work must always be unsettled and continuously work to decentre itself