The goal of this paper is to address the fact that server virtualization is still a relatively new technology undergoing rapid development and innovation. While creating a virtual machine is relatively simple, the underlying complexity of the infrastructure and IT processes cannot be ignored. Without the proper tools and processes in place, extending the value of virtualization can be extremely complex. Businesses have done a tremendous job achieving the initial benefits of the first wave of virtualization, but are quickly being challenged by the road blocks and intricacies that are stalling further implementation and even negating some of the benefits that virtualization had promised from the beginning.