If you are getting an error that says File cannot be found or a 404 error when you try to go to webmail.mydomain.com, this may help you out. The error occured right after i set "enable parent paths" to true on the website folder of iis. The problem was that the default mapping options overwrote ALL of my domains, including webmail. The problem is that the default mapping application extensions do not include php support. Here is how to fix this: Go to start - > Administrative Tools -> Internet Information Services (IIS) Manager Expand the server (local computer) Expand Web Sites Right click on webmail(default) and click Properties Go to the Home Directory tab Click on the Configuration button towards the bottom. In the list box that appears, if the extensions php, php3, and phtml do not exist, you have found your problem. Click Add For executable, type the location of the file php.exe mine was: "C:\Program Files\SWsoft\Plesk\Php\php.exe" (You need the " around the file if there is a space in the location) (If you cannot find it there, try searching for the file.) For extension, type: .php Leave everything else as default checked. Click ok. Repete this step using the same executable and adding the extensions: .php3 and .phtml Exit out of everything. Webmail should be up and running now. If it didnt help, im very sorry . If it did, great . Let me know if there is anything else i can do for you folks.