This article examines a developing trend in the prostitution industry in the western world, the boom in escort prostitution. Escort prostitution, operating through mobile phones and the Internet, is supplanting the brothel as the major form in which prostituted women are delivered to male buyers. Policy-makers who promote the legalization of the prostitution industry have argued that this policy will make prostituted women and girls safer and combat organized crime. These assumptions are based upon the idea that prostitution will take place in brothels which can institute health and safety codes, and enable easy identification of the illegal brothel industry which can be closed down. Escort prostitution provides particular challenges to the regulation of prostitution because there is no way in which it can be controlled or made “safe.” Alongside the other harms associated with prostitution which are exacerbated in legalized regimes, this development provides a significant reason why the policy of legalization is doomed to fail in achieving its objectives. The problems associated with the escort boom will be examined in relation to the state of Queensland in Australia, and the Netherlands, jurisdictions in which the prostitution industry has been legalized.