This article provides an analysis and critique of current legislative and judicial approaches to defining employment status. The backdrop for the analysis is the Agency Work Directive (AWD) 2008, and UK Regulations that implement it. It explores the significant changes and growing complexity in employment relationships themselves, with multilateral forms becoming more prominent. The article offers a new typology of employment relationships to reflect these changes. Case law from fiscal and company law as well as employment law is drawn on to illustrate some of the problems for law and policy of complex employment relationships. It is argued that law has failed to create a coherent approach to defining status and, specifically, that it has failed to appreciate the characteristics of emerging forms of self-employment, treating it as merely a default category of employment. The major implications for accessing employment rights are considered and the article concludes by making a series of recommendations for reform.