This article will critically argue that the regulation of behaviour in cyberspace is not simply the imposition through a top down system from regulator to regulated, a number of actors and elements come into play. In doing so, it will analyse the boundaries between public and private law, between national and international law and between state law and self regulation, and review whether the traditional positivist methodology of law, within these boundaries offers an adequate intellectual framework in which to consider the nature and form of regulation in cyberspace. Cyberspace is not a static regulatory universe into which an intervention can be made. Any response must acknowledge cyberspace’s dynamic, complex and peculiar nature, particularly its veil of anonymity and consequential challenges posed by Web v.2 and Web v.3. Hence, through the use of the example of cyber-stalking this article will consider the differences between offline and cyber-stalking, and review how these differences affect the nature of the regulation of such activities. These characteristics and differences should inform the debate about the nature and form of regulation of stalking in cyberspace and mean that it is not simply a question of transferring behaviours across from the physical world, communities in cyberspace are different and so is their behaviour. The explosion of social networking sites that encourage the posting of personal profiles, interests, blogs, photos, videos and online diaries and to the increased use of intelligent systems that enable much more sophisticated data-mining and machine learning means that within such environments which actively encourage users to share personal information and with tools that enable the capture and analysis of such data the opportunity and ability to cyber-stalk is greatly increased. Finally, the article will consider if any of the methodologies offered by authors such as Bert-Jaap Koops et al, Biegel and Murray could be adopted to meet the particular challenges of cyberstalking. References: Bert-Jaap Koops et al, Starting Points for ICT Regulation: Deconstructing Prevalent Policy One- Liners (The Hague:TMC Asser Press, 2006) Biegel, S. Beyond Our Control? Confronting the Limits of Our Legal System in the Age of Cyberspace (Cambridge, Mass: MIT Press, 2003) Gillespie, T. Wired Shut copyright and the shape of digital culture. (Cambridge, Mass: MIT, 2007 ) Lesssig, L. Code and Other Laws of Cyberspace, (London: Routedge, 1999) Murray, A. D. The Regulation of Cyberspace: Control in the Online Environment, (Abingdon: Routledge Cavendish, 2007)