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This article defines a legacy system as an aggregate package of software and hardware solutions whose languages, standards, codes, and technologies belong to a prior generation or era of innovation. By this definition, all technology solutions will ultimately become legacy systems. So IT professionals and managers should prepare to manage legacy systems throughout their careers, and software experts and engineers should focus not only on software development but also, after deployment, on the operational phase. Further more, organizations that use software and the vendors that sell and maintain it could benefit from an intentional, formalized, and data-driven approach for making decisions about legacy systems- that is, a systematic approach for evaluating them.