This article offers a reparative reading or a critique in solidarity of the discourse on privilege. Giving the practice of privilege checking and its theoretical underpinnings the benefit of the doubt, we analyse where it fails and how it could succeed. While the discourse on privilege rests on important insights about structural oppression and develops political productivity through disruptive elements, it is often misunderstood and misused as a political project in and of itself. By enriching the concept of privilege with an analysis of property relations and its epistemological dimensions, we aim to show pathways for more nuanced political dialogue that takes history and materiality seriously, starts from concrete situations and is oriented towards specific political goals.