Defining Cloud Computing can be difficult, as each organization often has its own spin on the definition. Despite being hard to define, Gartner Research named Cloud Computing as one of the top technologies to watch in 2010, 2011, and 2012. At its core, Cloud Computing is a technical architecture that meets a specific business need. This chapter traces the roots of Cloud Computing from its origins in mainframe distributed computing, discusses the basics of the Cloud Computing model today, and offers insights for future directions that are likely to be pursued in the Cloud Computing arena. A number of challenges to Cloud Computing are identified, including concerns of security and how to deal with the rise of mobile computing. The chapter ends with recommendations on how to choose which Cloud model is most appropriate to meet your organization’s needs and how to establish a successful Cloud strategy.