The tradition of classifying owner-drivers as contractors dates as far back as the 1950s and was affirmed anew in TNT Express Worldwide (NZ) Limited v Cunningham [1993] 3 NZLR 681 (CA). The Court of Appeal decision set an authoritative precedent with the effect of excluding a significant majority of owner-drivers in the courier transport industry from the protections of employment law. In the light of a new statutory regime, relevant judicial developments and changes in the character of the courier transport industry, this traditional classification has become contentious. This paper contends that TNT v Cunningham would be decided differently today. The Employment Relations Act 2000, with its inclusive approach to assessing the real nature of a relationship, has replaced the contractually focused Employment Contracts Act 1991. Subsequent judicial developments testify to the relegation of contractual terms as indicative of parties’ intent and the reduced importance of industry practice. Changes in the character of the industry, such as the increasing competitiveness of the tendering process and prevalence of migrant workers, have heightened the dependence of contractors on a single principal and reduced their bargaining power. Owner-drivers in the courier transport industry are de facto employees wrongfully denied the benefits of employment law.