The Taylor Review of Modern Working Practices 2017 states that ‘the way in which employment protections are applied, relies on individuals and employers understanding the type of relationship that exists between them – most basically, deciding whether the individual is an ‘employee’, a ‘worker’ or genuinely self-employed’. Concluding his report, Taylor found that, for numerous reasons, this categorisation was becoming more complex for an increasing proportion of the workforce; those in ‘atypical’ employment. In view of this complexity, this article seeks to analyse the law in which an individual is legally classified in their employment status. In particular, the article questions whether English law has released itself from its historic shackles of the binary divide between the employed and self-employed to protect those in atypical employment in modern working practice? Or has the judiciary over stretched the elastic of the legal framework leading to a need for legislative reform?