Exactions — a term used to describe certain conditions that are attached to land-use permits issued at the government’s discretion — ostensibly oblige property owners to internalize the costs of the expected infrastructural, environmental, and social harms resulting from development. This Article explores how proponents of progressive conceptions of property might respond to the open question of whether legislative exactions should be subject to the same level of judicial scrutiny to which administrative exactions are subject in constitutional takings cases. It identifies several first-order reasons to support the idea of immunizing legislative exactions from heightened takings scrutiny. However, it suggests that distinguishing between legislative and administrative measures in this context could produce several second-order consequences that actually undercut the goals of progressive property theory.