The main aim of this chapter is to analyse the contradictions among several verdicts in Spain about the legality of digital monitoring in the workplace, more specifically, the legal viability of reading workers’ e-mails. These contradictions arise mostly because of the use of two incompatible metaphors: e-mail as a company instrument and e-mail as a system to deliver letters. Nevertheless, the existence of these two metaphors is not mostly due to the judges’ lack of knowledge about digital media, but to political interests towards completely informating the workplace. If my analysis is correct, Spanish legal background does not allow the company instrument reading of the situation. E-mail as a letter is the only interpretation that should prevail.