An automated disaster recovery (DR) planning system for a computing environment is provided. A discovery module discovers servers, networks, and storage devices in a computing environment. An expert knowledge base module captures best practices in planning, and capabilities, interoperability, limitation and boundary values for different DR technologies. A match-making module determines multiple DR plans as combinations of one or more replication technologies that can be used to satisfy DR requirements. And, an optimizer configured for assessing a feasible DR plan from said multiple DR plans, to deploy for DR planning of a primary computing environment.