I don't see why not. I am looking at my 2008 web server answer file and it *could* work with Windows 7. But there are a couple things that may cause a problem, you'd have to test it. I can think of these issues: 1. The user account you specify would get created on both 7 and 2008 installs. This shouldn't be too big of a problem since you can just delete that user from 2008 afterwards. 2. Computername... both would get the same computer name. Probably should have it set to * to generate a random name if you want them to be different. 3. The fact that the Administrator account is disabled in 7 may cause a problem when trying to assign a password to it. 4. If you have any packages to configure, a 7 install may error if it doesn't have those packages... That being said, here is what you should do. Create 2 answer files, one for 7 and one for 2008. Then you need to create a new boot.wim that gives you an option to launch setup of either OS. So if you pick Windows 7, you run setup.exe /unattend:win7.xml, and obviously other option to install 2008 using its own XML. You specify the image number for each, say 7 is 1 and 2008 is 2.