This article considers the approach taken to devices that are designed to avoid tenancy legislation, exploring the doctrines of sham, pretence, contracting out and the “artificial device doctrine” developed in tax cases. It is argued that the legal response takes two stages. The first judicial task is to determine which legal route is being followed, an enquiry which is designed to identify what the genuine relationship is between the parties and incorporating the doctrines of sham, pretence and labelling. Having determined the true nature of the legal relationship, the task of the court is then to apply the legislation to that relationship, which will include a consideration of whether any “contracting out” by the tenant is lawful. Having reviewed the legal response to devices, the article discusses the decision of the Court of Appeal in Bankway Properties v Pensfold-Dunsford.