This article argues that attempts to regulate the private military and security industry have been stymied by a tendency to be constantly ‘regulating the last war’ or responding to the challenges of a previous manifestation of private force rather than dealing with the current challenges. It argues that states ought to more clearly consider the direction of the industry rather than regulate in response to crises, an approach that has left regulation unequipped to deal with two fields of PSC growth: the use of PSCs against piracy, and to deliver and support humanitarian aid.