People experiencing homelessness (PEH) are pressed to survive both in public spaces, where they face intense judicialization and criminalization, as well as in spaces of care, where they also experience punitive governance. Frontline service providers, in shelters, or conducting street outreach, regularly engage with security forces and the police. The social profiling and punitive control of PEH has been widely documented, yet little is known about the impacts of the COVID-19 pandemic on key issues important to practitioners and their clients. Our paper reports on 43 semi-structured interviews conducted with Montreal practitioners, focusing on local themes such as COVID tickets, encampments, and increased security forces in shelters. Engaging with work on the punitive governance of homelessness and a criminology of crisis, we analyze how frontline workers face challenges while also pushing to adapt, innovate and resist punitive approaches. Our work can help clarify when and how pandemic-related laws, regulations, police practices, and agency rules impact practitioners and the people they work with. We contribute to a better understanding of the control, punishment and exclusion of PEH and of legal violence, while also focusing on community and frontline resilience.