A system and method for automating the migration of configuration settings and data from computer systems running the Windows® operating system to computer systems running the Linux® operating system. The method utilizes data from one or more sources to create the configuration of the target system, and translates between settings related to the Windows® systems and Linux® systems involved. As a result, it simplifies the otherwise complex and time-consuming task of migrating from one server to another, specifically when migrating between two operating systems that provide similar functionality but are configured in distinctly different ways.