Everyone is talking about Cloud Computing, but there seems to be wildly differing perspectives on what it means, how it works, and the costs and benefits of such a model. When it comes to databases and other business critical applications in the cloud, the message is even more confusing. In this paper, we will share our lessons learned while helping some of the biggest companies in the world with their Cloud and Database as a Service (DBaaS) strategies. We will also share best practices and success stories around automating the provisioning and deployment of fully customized, complex application environments based on Oracle core database technology.