The deregulation of planning controls is often presented as a panacea that will help increase housing supply and give individuals more freedom to extract value from their property or properties. From the streamlining of planning regulation to the government’s red tape challenge, the answer to the provision of better outcomes for society appears to be: let the market decide. But is it always best or desirable to allow the market to arbitrate collective values? Is planning deregulation necessarily the answer? This short film examines the case of the extension of Permitted Development Rights to allow office to residential conversion and the partial deregulation of planning controls on short-term letting in London from the perspective of local government officers.