Unlike other housing courts, Chicago’s building court is characterized by leniency. The mostly low-income property owners who appear in building court often receive extensions to remedy building code violations or even dismissals of their violations. This article shows that, paradoxically, the consequences of these lenient outcomes are punitive for building court defendants, replicating the kinds of detrimental outcomes that harsher legal enforcement can produce. Building on conceptual apparatus from socio-legal studies, I identify two mechanisms—property markers and hassle of leniency—through which building court entrenches or even exacerbates housing precarity for low-income homeowners and small-time landlords. I argue that without additional support for low-income defendants, even well-intentioned leniency on the part of municipal officials and legal actors reinforces economic inequities in the housing market.