Cloud computing promises a radical shift in the provisioning of computing resources within the enterprise. This paper describes the challenges that decision makers face when assessing the feasibility of the adoption of cloud computing in their organizations, and describes our Cloud Adoption Toolkit, which has been developed to support this process. The toolkit provides a framework to support decision makers in identifying their concerns, and matching these concerns to appropriate tools/techniques that can be used to address them. Cost Modeling is the most mature tool in the toolkit, and this paper shows its effectiveness by demonstrating how practitioners can use it to examine the costs of deploying their IT systems on the cloud. The Cost Modeling tool is evaluated using a case study of an organization that is considering the migration of some of its IT systems to the cloud. The case study shows that running systems on the cloud using a traditional ‘always on’ approach can be less cost effective, and the elastic nature of the cloud has to be used to reduce costs. Therefore, decision makers have to model the variations in resource usage and their systems' deployment options to obtain accurate cost estimates. Copyright © 2011 John Wiley & Sons, Ltd.