@ryan woodsmall && @roelpaulo: Please stop posting misinformation! @jjmckenzie said it already, but I will say it again: SOME apps must be reinstalled, SOME don't. From my experience it goes like this: Games - about 99% works without reinstalation (some games use registry to store information like serial number - very, very, VERY bad idea - those usually must be reinstalled, or their registry key imported from Windos installation) Professional software - about 90% MUST be reinstalled - this is because, most of this programs uploads additional dll's and other components into Windos system/system32 folder, and create hell of a lot registry entries In other words - IT DEPENDS ON THE SOFTWARE if it must be reinstalled or not. I suggest you first try out your software like this: Code: wine start /Unix /path/to/the/exe If that doesn't work, and you are sure this is not wine's fault - reinstall.