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IT Autopilot is a flexible architecture to support the delivery of information technology (IT) systems management services. Complex services that involve several tools require integration between the tools and automated processes that can invoke multiple tools. Designed primarily for the small and mid-sized enterprise, the architecture of IT Autopilot allows it to be deployed as a set of local and remote services delivered by the enterprise or by service providers as a flexible and extensible service offering. The IT Autopilot integrated IT service management platform is able to combine different tools and services to create specific, customized IT service solutions. Using the analogy of an autopilot on an airplane, the pilot first performs a set of manual operations to get the airplane off the ground and flying. Next, the autopilot is engaged to carry on normal flight operations. In our vision, there is an initial manual configuration step before IT Autopilot is enabled to take over and maintain the customer's normal IT operational state. In this paper we explain our vision and describe the prototype system we have implemented.