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This paper describes the Software Technology Risk Advisor (STRA), a knowledge-based software engineering tool that provides assistance in identifying and managing software technology risks. The STRA contains a knowledge base of software product and process needs, satisfying capabilities and capability maturity factors. After a user ranks the importance of relevant needs to his or her project, the STRA automatically infers risk areas by evaluating disparities between project needs and technology maturities. Identified risks are quantitatively prioritized and the user is given risk reduction advice and rationale for each conclusion. This paper presents methods used in the STRA, along with discussions of knowledge acquisition experimental results, current status, and related work.