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Securing our digital assets has become increasingly challenging as our reliance on rapidly evolving technologies continues to grow. The security perimeter in computing has changed from a well-defined boundary that was relatively easy to identify and defend, to an elastic boundary that is constantly changing and for which the threats are constantly evolving. This paper investigates the complex security challenges that are introduced by the trend towards Infrastructure as a Service (IaaS)-based cloud computing. While not exhaustive, it identifies some technological and legal issues and concerns from the perspectives of identified stakeholders, and suggests some future directions for security research and development to help advance the security posture of this technology.