The emergence of so-called ‘gig work’, particularly that sold through digital platforms accessed through smartphone apps, has led to disputes about the proper classification of workers: Should platform workers be classified as independent contractors (as platforms typically insist), or as employees of the platforms through which they sell labor (as workers often claim)? Such disputes have urgency due to the way in which employee status is necessary to access certain benefits such as a minimum wage, sick pay, and so on. (...) In addition, classification disputes have philosophical significance because their resolution requires some foundational account of why the law should make a distinction between employed and freelance workers in the first place. This paper aims to fill this foundational gap. Central to it is the idea that employment involves a worker ceding certain freedoms in return for a degree of security, at least with respect to income. Insofar as the misclassification objection has force against digital platforms, it is when a platform is attempting to have it both ways: Workers are giving up freedom but not being granted a proportionate increase in security. As I shall explain, this approach offers some flexibility as to how actual disputes might be resolved – justice may be indifferent between whether platforms offer greater security or permit workers greater freedom, provided they do at least one of these things. (shrink)