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In this article we examine the challenges faced by data center administrators when deploying and configuring Web applications. We discuss how the configuration dependencies of these Web applications cut across software stacks, network layers, and middleware container boundaries. We argue that the deployment and configuration process requires the combined expertise from multiple domains such as application, middleware, network, security, reliability, and performance. We review the model-based tools available today to manage the configuration complexity of these applications and introduce a new tool that extends the existing state of the art by automatically generating actionable distributed deployment models using model transformation techniques. The key idea behind this new tool is the principle of separation of concerns: developers capture the logical structure of the application in a model, best practices experts define deployment model transformation rules, deployers specify the required deployment patterns, and an operator provides a model describing the data center resources. The tool automatically finds solutions based on these four inputs and executes the deployment.