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I have a client who wants to upgrade his Windows XP machine to Windows 7. He a lot of important software that he wishes to keep. Instead of doing a clean install of windows 7 and manually installing each and every program, could I do an upgrade of windows 7 without losing and installed programs or files? is this even possible? what would be the best route?

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No, you cannot, as the technicality in how the OS works is changed too much. You can, however, go from Windows XP to Vista (if you have the license), then to Windows 7, without losing your data. This Technet page explains all the upgrade paths available to Windows 7.

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