Since the 1970s, covenants running with the land have tethered a large majority of the new housing units produced in the United States. These private restraints usually continue for generations, until a majority or supermajority of covenant beneficiaries affirmatively vote to amend or terminate them. Covenants interact with public land use controls, particularly zoning ordinances. Zoning politics tends to freeze land uses in urban America, particularly in existing neighborhoods of single-family homes. This Article investigates to what extent covenants exacerbate the zoning freeze. It provides a history of the use of private covenants and suggests how drafters, judges, and legislators might address the risk that covenants will become obsolete.